S1
Catalyst-Free Facile Synthesis of Polycyclic Indole/Pyrrole
Substituted-1,2,3-triazoles
Jitendra Gour,a Srikanth Gatadi,a Ravikumar Akunuri,a Madhavi Venkata Yaddanpudi,a N.
Jagadeesh Babu,b Mushtaq Ahmad Nengroo,c Dipak Datta,c Sidharth Chopra,d and Srinivas
Nanduri* a
aNational Institute of Pharmaceutical Education and Research (NIPER) Hyderabad 500 037,
India
bCentre for X-ray Crystallography, CSIR-Indian Institute of Chemical Technology,
Hyderabad, 500607, India
cBiochemistry Division, CSIR-Central Drug Research Institute (CDRI), Lucknow-226031,
India.
dDivision of Microbiology, CSIR-Central Drug Research Institute, Sitapur Road, Sector 10,
Janakipuram Extension, Lucknow-226031, Uttar Pradesh, India
*Corresponding author: Dr. Srinivas Nanduri; E-mail: [email protected]
Table of Contents Page
ESI/MS experiments S3
Copies of 1H and 13C NMR spectrum of compound 1u’ S4
Determination of rate limiting step S5
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2019
S2
Table S1: Screening of solvents S6
Table S2: Growth inhibition of the tested compounds against cancer cells S7-S9
Table S3: MIC against ESKAP pathogen panel S9-S11
X-ray crystallography information and data S12-S14
Gram-scale reaction S14
Copies of 1H and 13C NMR spectrum of compound A- D S15-S18
Copies of 1H and 13C NMR spectrum of compound 1and 3 S19-S49
Copies of 1H and 13C NMR spectrum of compound 2a-x S50-S71
Copies of 1H and 13C NMR spectrum of compound 4a-h S72-S79
S3
ESI/MS experiments:
ESI/MS experiments were performed to gain evidence for the possible intermediates in
the proposed mechanism. The experiment was conducted under the optimal reaction
condition and the reaction was monitored after 1.5 h. The ESI/MS analyses showed a
peak of intermediates, which was identified as a triazoline species. We tried to isolate and
characterize the intermediate. We could not isolate dihydrotirazole, only we were able to isolate 1u’
under optimized reaction condition. We characterized and included NMR spectrum of compound
1u’.
Figure S1: ESI/MS spectra
S4
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1u’
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1u’
9 8 7 6 5 4 3 2 1 0 ppm
2.510
3.473
3.677
4.587
7.081
7.095
7.110
7.226
7.241
7.255
7.526
7.565
7.581
7.596
7.624
7.657
7.671
7.685
7.909
7.939
7.983
8.013
8.152
8.167
2.07
2.00
1.30
1.25
1.08
4.23
1.27
1.20
1.21
2.12
8.08.1 ppm
190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
39.34
39.51
39.67
39.84
40.01
40.09
40.17
40.34
42.53
51.44
105.28
111.00
121.09
121.70
122.45
124.17
127.74
128.90
129.32
132.43
133.61
135.83
138.05
138.90
188.97
S5
Determination of rate limiting step
The reaction of 1u (0.1 mmol) and sodium azide (0.13 mmol) was carried out in NMR tube
using DMSO-d6 as a solvent. The reactions were conducted for the specified time (such as 15
min, 30 min, 1 h, 2 h, 3 h, 6 h, 10 h and 20 h), then the progress of the reaction was monitored
by 1H NMR spectroscopy. Conversion of 1u to 1u’ (replacement of bromo to azide) which is
giving the corresponding cyclized product (2u) was estimated by the relative integration of
aliphatic proton( 1u: 4.82,3.82, 1u’: 4.59, 3.68 and 2u: 5.04, 4.69) and α, β-unsaturated ketone
protons. The results were listed in figure S2. We observed that the intramolecular azide-alkene
cycloaddition is slower than bromo to azide formation (1u to 1u’). Based on the result of figure
S2, it may be concluded that the intramolecular azide-alkene cycloaddition step is the rate
limiting step.
Figure S2: Progress of the reaction (1u-2u) monitored by 1H NMR (500 MHz, DMSO-d6).
S6
Table S1: Screening of solventsa
Entry Catalyst Solvent Yieldb(%)
1 None Chloroform 0
2 None DMSO 74
3 None THF 52
4 None Water Trace
5 None Methanol 61
6 None Ethanol 64
7 None Water: Methanol (2:1) Trace
8 None Water: Methanol (1:1) 11
9 None Water: Ethanol (1:1) Trace
10 None Acetone 60
11 None Water: Acetone (1:1) 86
12 None Water: Acetone (2:1) 26
13c None Water: Acetone (2:1) 56
14c None Water: Acetone (1:2) 68
14 None Water: DMF (1:1) 15
15 None Water: DMSO (1:1) 0
aReaction conditions: 1a (0.5 mmol) and NaN3 (0.6 mmol), solvent (5 mL) and the reaction was performed
at room temp for 20 h under air atmosphere. bYield of the products. Reaction was performed at room temp
for 36 h under air atmosphere
S7
Materials and Method:
Cell Lines
Multiple human cancer cell lines including HT-29 (colorectal adenocarcinoma), A549 (lung
carcinoma), PC-3 (prostate adenocarcinoma), MIA PaCa-2 (Pancreatic Carcinoma) and MCF-
7 (breast ductal carcinoma) were obtained from ATCC, USA. Early passage cells were
resuscitated from liquid nitrogen vapour stocks as needed and cultured according to the
manufacturer's instructions. Cells were routinely inspected microscopically for stable
phenotype, and all experiments were performed within early passages (within 10) of individual
cells.
Evaluation of in-vitro anticancer activity of synthetic compounds by Sulphorhodamine B
(SRB) calorimetric assay
Efficacy of the compounds as anticancer agents on various cancer cell lines was assessed using
standard Sulphorhodamine B (SRB) calorimetric assay for cytotoxicity screening as described
by before.1,2 Briefly, appropriate number of cells in 5% FBS containing medium were seeded
in 96 well plates and incubated at 37 °C in a humidified incubator with 5% CO2 until the cells
attached completely. The cells were treated with a single dose of compounds and were
incubated for further 48 hours. After an incubation period, cell monolayers were fixed with
10% (wt/vol) trichloroacetic acid followed by washing under slow running tap water. The cells
were stained with SRB dye for 30 minutes, after which the excess dye was removed by washing
3-4 times with 1% (vol/vol) acetic acid. The protein-bound dye is dissolved in 10 mM Tris
base solution for OD determination at 510 nm using a microplate reader (Epoch Microplate
Reader, Biotek, USA). Percentage of cell growth inhibition was calculated using the formula
[100-(Absorbance of compound treated cells/ Absorbance of control cells)] X 100.2
S8
References
1. Vichai, V.; Kirtikara, K., Sulforhodamine B colorimetric assay for cytotoxicity
screening. Nat. Protoc. 2006, 1 , 1112.
2. Maheshwari, S.; Avula, S. R.; Singh, A.; Singh, L. R.; Palnati, G. R.; Arya, R.
K.; Cheruvu, S. H.; Shahi, S.; Sharma, T.; Meena, S., Discovery of a Novel Small-
Molecule Inhibitor that Targets PP2A–β-Catenin Signaling and Restricts Tumor
Growth and Metastasis. Mol. Cancer Ther. 2017, 16, 1791-1805.
Table S2: Percentage Growth inhibition of the tested compounds against human cancer
cell line at 10 µM.
HT-29
(Colon)
MCF-7
(Breast) A549 (Lung) MIA PaCa-2
(Pancreatic) PC-3
(Prostate) Compound Average ± SE Average ± SE Average ± SE Average ± SE Average ± SE 2a
9.95± 6.86
21.2±3.06 8.55±5.79 10.81±0.16 9.47±0.00
2b
15.39±8.9 25.43±0.95 17.22±6.83 14.96±0.03 16.62±2.10
2c
26.91±7.07
24.89±1.33 19.97±5.99 24.84±2.33 13.27±1.38
2d
22.75±4.62
30.39±0.60 14.61±7.15 16.16±0.86 16.78±3.80
2e
7.64±3.87
20.47±0.93 9.69±8.72 0.39±2.43 8.70±0.92
2f
40.1±5.45
33.29±1.11 22.79±10.67 30.28±2.17 16.05±4.25
2g
5.71±6.59
19±5.68 8.41±10.22 20.71±12.23 18.89±4.31
2h
15.38±6.20
20.29±4.73 10.24±10.35 17.33±1.53 14.95±3.05
2i
-3.18±8.45 33.43±5.47 5.3±1.38 5.27±0.60 2.27±3.05
2j 8.1±3.24 26.31±7.16 10.86±3.18 19.87±1.39 18.53±1.47
2k
17.13±1.07 32.05±6.15 18.04±2.44 21.09±0.75 7.05±0.91
2m
7.75±1.18
23.07±0.92 13.12±3.60 7.91±1.00 3.07±0.71
2n
38.51±4.75
47.25±0.40 40.78±3.74 36.42±1.87 37.45±1.00
S9
2o
0.57±3.50
27.79±2.00 8.54±5.04 7.17±0.08 8.36±3.97
2p
3.19±4.41
27.85±6.22 16.68±10.04 7.90±4.42 11.17±0.33
2q
10.5±4.67
34.58±2.81 22.32±3.98 19.90±6.80 29.27±5.74
2r
1.59±2.70
27.4±0.65 13.27±10.46 19.97±10.22 19.67±3.82
2s
19.67±0.56
23.81±2.53 14.41±11.12 18.73±1.95 17.34±2.75
2t
-3.9±3.48
45.48±6.01 36.54±1.62 37.80±1.83 39.64±1.00
2u
-9.42±5.33
33.07±5.13 14.11±2.52 15.41±1.19 6.30±1.92
2v
-8.57±0.31
23.68±7.18 10.57±0.34 5.10±4.53 -3.20±0.51
2x
34.57±14.5
40.85±6.76 38.79±5.19 27.89±17.75 29.99±1.54
4a 21.25±0.59
39.36±7.39 29.74±2.51 14.62±4.52 20.19±0.47
4b
-13.93±3.28
18.81±2.03 12.68±1.92 26.99±13.70 -8.01±0.21
4c
NT NT NT NT
4d
-10.4±5.49
33.95±6.31 3.02±1.52 11.92±8.50 -7.34±3.90
4f
8.32±7.39
35.8±4.17 18.8±6.40 21.66±13.92 6.31±0.05
4g
-1.76±3.06
28.37±6.48 13.18±1.24 5.35±0.70 3.37±3.20
4h
-9.07±4.34
18.91±5.65 10.37±1.95 16.71±3.20 -1.61±2.43
NT = Not Tested
Antibiotic susceptibility testing against ESKAP pathogen panel
Antibiotic susceptibility testing was carried out on the newly synthesized compounds by
determining the Minimum Inhibitory Concentration (MIC) according to the standard CLSI
guidelines.3,4 MIC is defined as the minimum concentration of compound at which visible
bacterial growth is inhibited. Bacterial cultures were grown in Mueller-Hinton cation
supplemented broth (CA-MHB). Optical density (OD600) of the cultures was measured,
followed by dilution for ~106 CFU/mL. This inoculum was added into a series of test wells in
a microtitre plate that contained various concentrations of compound under test ranging from
64-0.03 µg/mL. Controls i.e., cells alone and media alone (without compound+cells) and
S10
Levofloxacin used as a reference standard. Plates were incubated at 37 °C for 16-18 h followed
by observations of MIC values by the absence or presence of visible growth. For each
compound, MIC determinations were performed independently thrice using duplicate samples
each time.
References
3. Jorgensen, J. H.; Hindler, J. F.; Reller, L. B.; Weinstein, M. P., New consensus
guidelines from the Clinical and Laboratory Standards Institute for antimicrobial
susceptibility testing of infrequently isolated or fastidious bacteria. Clin. Infect. Dis.
2007, 44, 280-286.
4. Pandey, M.; Singh, A. K.; Thakare, R.; Talwar, S.; Karaulia, P.; Dasgupta, A.;
Chopra, S.; Pandey, A. K., Diphenyleneiodonium chloride (DPIC) displays broad-
spectrum bactericidal activity. Nat. Protoc. 2017, 7, 11521.
Table S3: MIC (µg/mL) of indolo- and pyrrolo[1,4]diazepines/pyrazines against ESKAP
pathogen panel
Compound
Gram +ve Gram -ve
S. aureus
ATCC
29213
E. coli
ATCC
25922
K.
pneumoni
ae
BAA-
1705
A. baumannii
BAA 1605
P. aeruginosa
ATCC 27853
2a >64
>64 >64 >64 >64
2b 64
>64 >64 >64 >64
2c >64
>64 >64 >64 >64
2d >64
>64 >64 >64 >64
S11
2e >64 >64 >64 >64 >64
2f >64 >64 >64 >64 >64
2g 16 >64 >64 >64 >64
2h >64 >64 >64 >64 >64
2i >64 >64 >64 >64 >64
2j
>64 >64 >64 >64 >64
2k
8 >64 >64 >64 >64
2m
>64 >64 >64 >64 >64
2n
8 >64 >64 >64 >64
2o >64
>64 >64 >64 >64
2p >64 >64 >64 >64 >64
2q >64 >64 >64 >64 >64
2r >64 >64 >64 >64 >64
2s 32 >64 >64 >64 >64
2t >64 >64 >64 >64 >64
2u >64 >64 >64 >64 >64
2v >64 >64 >64 >64 >64
2x NT NT NT NT NT
4a >64 >64 >64 >64 >64
4b NT NT NT NT NT
4c >64 >64 >64 >64 >64
4d >64 >64 >64 >64 >64
4e NT NT NT NT NT
4f >64 >64 >64 >64 >64
4g >64 >64 >64 >64 >64
4h >64 >64 >64 >64 >64
Levofloxacin <0.5 <0.5 64 8 1
NT = Not Tested
S12
X-ray crystallography information and data
Figure S3. The molecular structure of KA555 (compound 2j) with the atom-numbering
scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown
as small spheres of arbitrary radius. CCDC 1887445 contains the supplementary
crystallographic data.
Sample preparation: Compound 2j was dissolved in ethanol (100 mg in 3 mL ethanol) and
allowed for crystallization at room temperature for 7-8 days.
Table S4: Crystal data and structure refinement.
Identification code KA555
Chemical formula C22H19N5O2
Molecular weight 385.42
Temperature 293(2)K
Wavelength 0.71073Å
Crystal system ; space group monoclinic ; P 21/c
Unit cell dimensions
A = 14.4652(12)Å
b = 15.665(3)Å
c = 8.435(2)Å
α = 90 °
β = 91.931(7) °
γ = 90 °
Volume 1910.2(6) ų
Z, Calculated density 4, 1.340 g/cm³
Absorption coefficient 0.090 1/mm
F(000) 808
Theta range for data collection 2.600° to 27.500°
Limiting indices -18 <= h <= 18 ; -20 <= k <= 20 ; -10 <= l <= 10
S13
Reflection collected / unique 34927 / 4384 [R(int) = 0.0710]
Completeness to theta max 99.9 %
Refinement method Full-matrix least-square on F²
Data / restraints / parameters 4384 / 72 / 296
Goodness of fit on F² 1.172
Final R indices [I>2sigma(I)] R1 = 0.0533 ; wR2 = 0.1497
Final R indices [all data] R1 = 0.0772 ; wR2 = 0.1703
Largest diff peak and hole 0.376 and -0.251 e/ų
Data collection and structure solution of KA555 (2j): Single crystal X-ray data for two
compounds were collected at room temperature on a Bruker D8 QUEST equipped with a four-
circle kappa diffractometer and Photon 100 detector. An Iμs microfocus Mo source
(l=0.71073Å) supplied the multi-mirror monochromated incident beam. A combination of Phi
and Omega scans were used to collect the necessary data. Unit cell dimensions were determined
using 9898 reflections. Integration and scaling of intensity data were accomplished using
SAINT program.1 The structures were solved by Direct Methods using SHELXS972 and
refinement was carried out by full-matrix least-squares technique using SHELXL-2014/7.2-3
Anisotropic displacement parameters were included for all non-hydrogen atoms. All H atoms
were positioned geometrically and treated as riding on their parent C atoms with C-H distances
of 0.93--0.97 Å, and with Uiso(H) = 1.2Ueq (C) or 1.5Ueq for methyl atoms. CCDC 1887445
contains the supplementary crystallographic data for this paper which can be obtained free of
charge at https://summary.ccdc.cam.ac.uk/structure-summary-form or from the
Cambridge Crystallographic Data Centre (CCDC), 12 Union Road, Cambridge CB2 1EZ, UK;
fax: +44(0) 1223 336 033; email: [email protected].
S14
SMART & SAINT. Software Reference manuals. Versions 6.28a & 5.625, Bruker Analytical
X-ray Systems Inc., Madison, Wisconsin, U.S.A., 2001.
Sheldrick, G. M. SHELXS97 and SHELXL Version 2014/7, http://shelx.uni-
ac.gwdg.de/SHELX/index.php
Muller, P, Herbst-Imer, R, Spek, A. L, Schneider, T. R, and Sawaya, M. R. Crystal Structure
Refinement: A Crystallographer’s Guide to SHELXL. Muller, P. Ed. 2006 Oxford University
Press: Oxford, New York, pp. 57–91.
Scheme S1. Gram-scale reaction.
S15
1H NMR (500 MHz, DMSO-d6) spectrum of compound A
13C NMR (125 MHz, DMSO-d6) spectrum of compound A
10 9 8 7 6 5 4 3 2 1 0 ppm
2.213
2.227
2.240
2.254
2.268
2.511
2.513
3.365
3.467
3.481
3.494
4.618
4.632
4.646
7.165
7.179
7.195
7.421
7.437
7.452
7.491
7.654
7.671
7.774
7.790
9.897
9.899
2.03
2.06
2.00
1.05
1.02
0.95
1.03
1.09
1.02
200 180 160 140 120 100 80 60 40 20 0 ppm
31.72
33.82
39.54
39.71
39.88
40.04
40.21
40.38
40.54
43.24
111.38
118.32
121.39
123.84
126.39
127.30
135.50
140.26
183.78
S16
1H NMR (500 MHz, CDCl3) spectrum of compound B
13C NMR (125 MHz, CDCl3 + DMSO-d6) spectrum of compound B
10 9 8 7 6 5 4 3 2 1 0 ppm
3.656
3.670
3.684
4.864
4.878
4.891
7.178
7.181
7.191
7.194
7.197
7.208
7.210
7.244
7.300
7.301
7.418
7.420
7.431
7.435
7.437
7.448
7.450
7.458
7.475
7.725
7.739
7.741
9.854
2.18
2.18
1.06
1.06
2.17
1.02
1.00
200 180 160 140 120 100 80 60 40 20 0 ppm
35.28
44.38
44.55
44.72
44.88
45.05
45.22
50.66
82.44
82.70
82.85
82.95
115.49
123.63
126.24
128.22
131.10
132.12
139.79
145.12
187.28
S17
1H NMR (500 MHz, DMSO-d6) spectrum of compound C
13C NMR (125 MHz, DMSO-d6) spectrum of compound C
10 9 8 7 6 5 4 3 2 1 0 ppm
2.503
2.507
2.511
2.514
2.518
3.331
3.739
3.752
3.764
4.644
4.657
4.670
6.266
6.271
6.274
6.279
7.096
7.099
7.104
7.107
7.372
9.514
9.515
200 180 160 140 120 100 80 60 40 20 0 ppm
33.16
39.52
39.69
39.86
40.03
40.12
40.19
40.28
40.36
40.45
40.53
49.72
109.96
125.62
131.28
133.35
180.04
S18
1H NMR (500 MHz, DMSO-d6) spectrum of compound D
13C NMR (125 MHz, DMSO-d6) spectrum of compound D
10 9 8 7 6 5 4 3 2 1 0 ppm
2.193
2.207
2.220
2.234
2.247
2.505
2.508
2.512
3.329
3.389
3.402
3.416
4.370
4.383
4.397
6.250
6.255
6.258
6.263
7.056
7.059
7.063
7.067
7.303
9.514
2.04
2.01
2.00
0.92
0.94
0.98
0.92
180 160 140 120 100 80 60 40 20 0 ppm
31.49
34.09
39.53
39.70
39.86
40.03
40.20
40.37
40.53
47.13
110.04
125.22
131.37
132.69
179.77
S19
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1a
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1a
10 9 8 7 6 5 4 3 2 1 0 ppm
2.208
2.221
2.235
2.249
2.262
2.509
2.512
2.516
3.352
3.514
3.527
3.539
4.503
4.517
4.531
7.095
7.111
7.125
7.250
7.252
7.267
7.281
7.505
7.579
7.596
7.612
7.634
7.650
7.669
7.671
7.686
7.699
7.701
7.933
7.964
7.994
8.024
8.171
8.174
8.188
2.06
2.06
2.00
1.02
1.04
1.06
2.95
1.02
1.09
1.01
1.08
1.99
7.47.57.67.77.87.98.0 ppm
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
31.95
33.89
39.52
39.69
39.86
40.02
40.19
40.28
40.36
40.52
41.51
105.11
110.77
120.97
121.79
122.67
124.15
127.64
128.91
129.29
132.21
133.56
135.43
138.11
138.89
188.89
S20
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1b
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1b
9 8 7 6 5 4 3 2 1 0 ppm
2.140
2.147
2.511
2.515
3.360
3.368
3.434
3.445
4.363
7.079
7.088
7.094
7.101
7.117
7.239
7.247
7.250
7.256
7.261
7.264
7.269
7.279
7.301
7.311
7.369
7.378
7.449
7.456
7.460
7.465
7.470
7.474
7.479
7.486
7.490
7.520
7.528
7.543
7.545
7.550
7.555
7.558
7.560
7.564
7.570
7.581
7.606
7.613
7.622
7.629
7.741
7.749
7.757
7.765
2.01
2.02
2.00
0.99
1.95
1.02
1.05
3.87
1.12
0.96
200 180 160 140 120 100 80 60 40 20 0 ppm
31.88
33.56
39.53
39.69
39.86
40.03
40.19
40.28
40.36
40.53
41.40
105.67
110.87
119.22
121.10
121.97
124.51
126.44
127.62
128.37
129.73
132.26
133.69
134.59
139.07
141.18
193.93
S21
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1c
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1c
11 10 9 8 7 6 5 4 3 2 1 0 ppm
2.199
2.212
2.225
2.240
2.253
2.502
2.505
2.509
2.512
2.516
3.335
3.505
3.518
3.531
4.495
4.510
4.524
7.091
7.093
7.107
7.122
7.123
7.249
7.252
7.263
7.266
7.268
7.280
7.282
7.511
7.571
7.572
7.588
7.629
7.645
7.780
7.785
7.788
7.798
7.802
7.926
7.956
7.965
7.996
8.096
8.101
8.104
8.114
8.118
8.123
2.16
2.11
2.00
1.08
1.07
1.11
1.07
1.13
2.05
1.11
1.00
2.03
200 180 160 140 120 100 80 60 40 20 0 ppm
31.94
33.88
39.54
39.70
39.87
40.04
40.20
40.29
40.37
40.46
40.54
41.50
105.35
110.80
121.01
121.84
122.25
124.27
127.63
127.69
130.92
132.33
132.66
135.35
137.11
138.95
187.98
S22
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1d
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1d
11 10 9 8 7 6 5 4 3 2 1 0 ppm
2.199
2.212
2.225
2.239
2.253
2.509
2.512
2.516
3.364
3.509
3.522
3.535
4.499
4.513
4.527
7.094
7.109
7.124
7.253
7.269
7.283
7.565
7.573
7.590
7.602
7.617
7.633
7.649
7.664
7.731
7.733
7.745
7.747
7.749
7.947
7.962
7.978
8.002
8.032
8.118
8.120
8.134
8.136
8.189
8.193
8.205
8.208
2.00
2.03
2.00
1.04
1.05
2.13
1.95
1.09
1.01
1.08
1.04
1.01
200 180 160 140 120 100 80 60 40 20 0 ppm
31.95
33.89
39.51
39.68
39.85
40.01
40.18
40.27
40.35
40.52
41.49
105.61
110.81
121.03
121.86
122.13
124.32
127.52
127.63
128.56
131.23
132.92
133.24
134.34
135.32
138.98
139.95
187.61
S23
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1e
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1e
9 8 7 6 5 4 3 2 1 0 ppm
1.909
1.921
1.932
2.512
3.182
3.192
3.212
3.224
3.235
3.364
4.397
4.410
4.422
6.171
6.647
6.664
7.064
7.078
7.093
7.203
7.218
7.233
7.361
7.488
7.505
7.594
7.610
7.788
7.819
7.907
7.942
7.960
2.13
2.22
2.11
2.05
2.00
0.98
1.05
1.04
1.06
0.98
1.01
3.01
200 180 160 140 120 100 80 60 40 20 0 ppm
30.67
39.50
39.66
39.83
40.00
40.17
40.33
40.50
49.08
58.39
103.67
110.64
113.26
120.62
121.41
123.09
123.49
125.86
127.68
129.96
131.49
136.10
138.60
154.34
185.72
S24
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1f
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1f
9 8 7 6 5 4 3 2 1 0 ppm
0.880
0.893
1.863
1.877
1.890
1.904
1.917
1.931
1.944
2.203
2.216
2.230
2.244
2.257
2.506
2.510
2.513
2.548
2.563
3.336
3.510
3.523
3.535
4.496
4.511
4.524
7.090
7.104
7.119
7.242
7.244
7.258
7.272
7.274
7.355
7.372
7.483
7.572
7.589
7.626
7.641
7.909
7.940
7.979
8.009
8.091
8.107
6.03
1.03
2.05
2.17
1.97
2.00
1.01
1.04
2.00
0.97
1.02
1.01
1.01
1.04
1.97
200 180 160 140 120 100 80 60 40 20 0 ppm
22.60
30.01
31.92
33.90
39.53
39.70
39.87
40.03
40.20
40.29
40.37
40.46
40.53
41.51
44.96
104.91
110.74
120.93
121.74
122.82
124.06
127.66
128.93
129.83
131.82
135.50
135.91
138.84
147.47
188.41
S25
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1g
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1g
10 9 8 7 6 5 4 3 2 1 ppm
1.901
1.914
1.926
1.938
1.951
2.510
3.200
3.212
3.223
3.348
4.416
4.429
4.443
7.067
7.072
7.076
7.083
7.090
7.106
7.229
7.245
7.259
7.379
7.394
7.410
7.458
7.485
7.489
7.493
7.510
7.526
7.614
7.629
7.644
7.659
7.905
9.816
2.04
2.13
2.00
2.05
1.05
1.07
0.98
1.01
1.05
1.05
1.03
2.03
1.02
200 180 160 140 120 100 80 60 40 20 0 ppm
30.62
39.53
39.69
39.86
40.03
40.20
40.28
40.36
40.45
40.53
58.36
68.81
104.79
110.79
115.02
119.91
120.69
120.79
121.69
122.42
124.00
127.62
130.32
132.32
135.61
138.89
139.62
158.24
188.83
S26
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1h
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1h
9 8 7 6 5 4 3 2 1 0 ppm
2.205
2.217
2.231
2.244
2.257
2.513
3.382
3.505
3.518
3.531
3.885
4.489
4.503
4.517
7.092
7.106
7.123
7.239
7.255
7.269
7.486
7.565
7.582
7.629
7.644
7.658
7.661
7.911
7.929
7.933
7.939
8.006
8.037
2.08
2.09
5.99
2.00
2.01
1.14
1.19
1.10
2.10
1.94
1.05
200 180 160 140 120 100 80 60 40 20 0 ppm
31.92
33.88
39.52
39.69
39.86
40.03
40.19
40.36
40.53
41.50
56.08
56.24
104.71
110.70
111.26
111.40
120.90
121.66
122.77
123.69
123.95
127.68
131.05
131.25
135.62
138.78
149.31
153.70
187.08
S27
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1i
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1i
10 9 8 7 6 5 4 3 2 1 0 ppm
2.203
2.216
2.230
2.244
2.256
2.507
2.510
2.514
3.344
3.513
3.525
3.538
4.502
4.517
4.531
7.094
7.109
7.124
7.250
7.251
7.266
7.280
7.401
7.418
7.436
7.512
7.522
7.556
7.577
7.593
7.632
7.648
7.926
7.957
7.973
8.002
8.033
8.242
8.260
8.264
8.271
8.278
8.285
8.289
2.02
2.00
2.03
1.04
1.07
2.09
1.09
1.05
1.08
1.01
1.03
2.04
200 180 160 140 120 100 80 60 40 20 0 ppm
31.96
33.89
39.51
39.68
39.85
40.01
40.10
40.18
40.27
40.35
40.44
40.51
40.60
41.49
105.18
110.78
116.21
116.39
120.98
121.80
122.41
124.19
127.62
131.86
131.94
132.35
134.77
134.79
135.39
138.89
164.51
166.51
187.41
S28
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1j
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1j
11 10 9 8 7 6 5 4 3 2 1 0 ppm
2.094
2.209
2.222
2.236
2.250
2.263
2.510
3.338
3.514
3.527
3.539
4.504
4.518
4.532
7.095
7.110
7.125
7.253
7.268
7.283
7.453
7.504
7.520
7.535
7.579
7.596
7.632
7.648
7.868
7.878
7.899
7.920
7.951
8.260
10.180
3.11
2.03
1.98
2.00
1.05
1.04
1.02
1.15
0.98
1.09
4.19
1.02
1.08
200 180 160 140 120 100 80 60 40 20 0 ppm
24.50
31.95
33.88
39.50
39.67
39.84
40.01
40.09
40.17
40.26
40.34
40.43
40.51
40.60
41.52
104.96
110.78
118.94
120.99
121.81
122.76
123.78
123.93
124.18
127.63
129.69
132.32
135.39
138.62
138.90
140.30
169.09
188.85
S29
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1k
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1k
9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
2.198
2.211
2.225
2.239
2.251
2.511
2.514
3.354
3.507
3.520
3.532
4.498
4.512
4.526
7.096
7.111
7.126
7.258
7.273
7.288
7.540
7.576
7.593
7.637
7.653
7.934
7.950
7.985
7.990
8.021
8.330
8.347
2.06
2.00
2.01
1.00
1.01
0.96
1.03
1.00
3.93
1.90
200 180 160 140 120 100 80 60 40 20 0 ppm
31.94
33.86
39.51
39.68
39.84
40.01
40.10
40.18
40.27
40.34
40.43
40.51
40.60
41.49
105.63
110.83
121.05
121.91
122.28
123.24
124.40
125.41
126.19
126.22
127.61
129.65
132.42
132.67
132.93
133.18
133.27
135.24
139.03
141.38
188.31
S30
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1m
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1m
9 8 7 6 5 4 3 2 1 0 ppm
2.248
2.261
2.274
2.289
2.301
2.464
2.551
2.554
2.557
3.386
3.558
3.571
3.584
4.543
4.557
4.571
7.136
7.151
7.166
7.289
7.305
7.320
7.433
7.449
7.538
7.547
7.619
7.635
7.671
7.687
7.952
7.983
8.030
8.061
8.129
8.145
2.13
3.09
2.19
2.00
1.16
1.22
2.14
1.13
1.08
1.09
1.16
1.10
2.04
200 180 160 140 120 100 80 60 40 20 0 ppm
21.68
31.95
33.90
39.52
39.69
39.85
40.02
40.19
40.36
40.52
41.51
104.92
110.75
120.94
121.74
122.74
124.07
127.66
129.06
129.86
131.83
135.50
135.59
138.84
144.01
188.29
S31
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1n
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1n
10 9 8 7 6 5 4 3 2 1 0 ppm
2.189
2.202
2.216
2.231
2.243
2.502
2.505
2.509
2.512
2.516
3.335
3.503
3.516
3.528
4.500
4.515
4.529
7.118
7.123
7.136
7.141
7.155
7.160
7.406
7.410
7.425
7.430
7.511
7.605
7.614
7.623
7.632
7.926
7.944
7.957
7.960
8.007
8.037
8.336
8.352
2.00
2.02
2.00
0.98
0.96
0.96
1.00
2.92
1.07
2.02
200 180 160 140 120 100 80 60 40 20 0 ppm
31.87
33.88
39.51
39.68
39.84
40.01
40.10
40.18
40.27
40.34
40.43
40.51
40.60
41.75
105.15
105.19
105.86
106.05
112.15
112.23
112.74
112.96
123.12
125.40
126.22
126.25
127.64
127.72
129.71
132.48
132.74
132.91
132.99
135.73
136.83
141.26
157.16
159.02
188.38
S32
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1o
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1o
10 9 8 7 6 5 4 3 2 1 0 ppm
2.188
2.200
2.215
2.228
2.241
2.507
2.511
2.514
3.492
3.505
3.517
4.478
4.492
4.506
7.084
7.099
7.114
7.240
7.256
7.270
7.511
7.526
7.542
7.549
7.570
7.606
7.622
7.638
7.832
7.834
7.836
7.848
7.850
7.852
7.937
7.968
7.980
8.011
8.149
8.164
8.324
8.327
8.331
2.10
2.01
2.00
1.03
1.04
3.02
1.13
1.01
0.90
1.11
0.96
0.92
180 160 140 120 100 80 60 40 20 0 ppm
31.91
33.88
39.54
39.70
39.87
40.04
40.20
40.37
40.54
41.49
105.64
110.78
121.01
121.86
122.07
122.84
124.31
127.64
127.86
131.42
132.88
135.31
136.09
138.98
140.13
187.50
S33
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1p
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1p
9 8 7 6 5 4 3 2 1 0 ppm
2.509
2.512
3.321
3.821
3.834
3.846
4.837
4.849
4.862
7.112
7.126
7.141
7.255
7.269
7.284
7.549
7.565
7.581
7.587
7.607
7.624
7.640
7.655
7.880
7.896
7.943
7.973
7.992
8.022
8.167
8.183
8.341
2.10
2.00
1.13
1.23
4.39
1.07
1.04
1.20
1.01
1.00
200 180 160 140 120 100 80 60 40 20 0 ppm
32.87
39.53
39.70
39.86
40.03
40.12
40.20
40.29
40.37
40.46
40.53
40.62
44.35
105.67
111.22
121.19
121.75
121.95
122.82
124.29
127.69
127.91
131.43
131.52
133.35
135.73
136.16
138.89
140.17
187.64
S34
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1q
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1q
9 8 7 6 5 4 3 2 1 0 ppm
0.887
0.900
1.871
1.885
1.898
1.912
1.925
1.939
1.952
2.509
2.512
2.515
2.557
2.572
3.348
3.818
3.830
3.843
4.825
4.838
4.850
7.106
7.121
7.136
7.242
7.258
7.273
7.329
7.365
7.382
7.505
7.599
7.616
7.634
7.649
7.914
7.945
7.983
8.013
8.103
8.120
6.24
1.05
2.20
2.02
2.00
1.02
1.06
2.02
1.04
0.95
0.99
1.08
1.04
2.06
200 180 160 140 120 100 80 60 40 20 0 ppm
22.61
30.03
32.82
39.50
39.66
39.83
40.00
40.16
40.25
40.33
40.42
40.50
44.35
44.96
104.98
111.14
121.11
121.64
122.56
124.05
127.71
128.95
129.85
132.18
135.90
138.73
147.51
188.40
S35
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1r
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1r
11 10 9 8 7 6 5 4 3 2 1 0 ppm
2.505
2.509
2.512
3.349
3.817
3.829
3.842
4.829
4.841
4.854
7.108
7.123
7.138
7.249
7.251
7.265
7.280
7.281
7.582
7.598
7.605
7.614
7.621
7.637
7.654
7.732
7.734
7.736
7.748
7.750
7.752
7.948
7.979
7.995
8.026
8.125
8.141
8.207
8.211
8.214
2.11
2.00
1.11
1.09
4.23
1.05
1.05
1.13
1.01
1.04
200 180 160 140 120 100 80 60 40 20 0 ppm
32.85
39.52
39.69
39.86
40.03
40.19
40.28
40.36
40.45
40.53
44.34
105.65
111.19
121.19
121.75
121.95
124.29
127.53
127.69
128.57
131.24
133.25
133.32
134.34
135.73
138.88
139.96
187.67
S36
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1s
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1s
9 8 7 6 5 4 3 2 1 0 ppm
2.513
3.336
3.806
3.818
3.831
3.878
3.909
3.952
4.783
4.795
4.807
6.664
6.668
6.681
6.685
6.718
6.722
7.094
7.109
7.124
7.223
7.245
7.259
7.590
7.607
7.613
7.620
7.629
7.651
7.665
7.683
7.746
7.777
2.18
3.00
3.03
2.00
0.97
0.95
1.07
2.05
4.10
1.21
200 180 160 140 120 100 80 60 40 20 0 ppm
32.55
39.52
39.69
39.86
40.03
40.12
40.19
40.28
40.36
40.45
40.53
40.61
44.46
56.12
56.53
99.11
104.38
106.62
111.03
121.02
121.52
121.82
123.85
127.71
129.94
132.67
135.97
138.72
160.80
164.56
188.85
S37
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1t
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1t
10 9 8 7 6 5 4 3 2 1 0 ppm
2.507
2.511
2.514
3.343
3.819
3.831
3.843
4.825
4.837
4.849
7.069
7.073
7.085
7.089
7.105
7.120
7.134
7.242
7.244
7.258
7.273
7.382
7.398
7.413
7.491
7.494
7.504
7.602
7.619
7.628
7.644
7.651
7.667
7.913
9.817
2.07
2.00
0.93
1.02
1.06
1.06
1.97
3.17
2.16
1.09
200 180 160 140 120 100 80 60 40 20 0 ppm
32.80
39.51
39.68
39.84
40.01
40.10
40.18
40.27
40.35
40.43
40.51
44.35
105.03
111.15
115.03
119.98
120.74
121.11
121.66
122.63
124.08
127.71
130.34
132.37
135.83
138.76
139.56
158.24
188.82
S38
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1u
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1u
10 9 8 7 6 5 4 3 2 1 0 ppm
2.510
2.513
3.346
3.824
3.837
3.849
4.832
4.844
4.856
7.111
7.126
7.141
7.249
7.263
7.265
7.279
7.525
7.586
7.602
7.618
7.640
7.656
7.675
7.677
7.691
7.704
7.707
7.934
7.965
7.973
7.975
7.991
8.021
8.178
8.195
2.00
1.99
1.06
1.03
1.19
4.17
1.16
1.02
1.18
2.00
200 180 160 140 120 100 80 60 40 20 0 ppm
32.81
39.53
39.70
39.87
40.03
40.20
40.37
40.53
44.37
105.17
111.16
121.14
121.69
122.47
124.13
127.71
128.92
129.30
132.59
133.57
135.83
138.13
138.80
188.93
S39
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1v
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1v
9 8 7 6 5 4 3 2 1 0 ppm
0.915
0.920
0.930
0.945
1.598
1.612
1.627
1.642
2.197
2.211
2.225
2.502
2.506
2.510
2.513
2.517
2.703
2.717
2.731
3.329
3.496
3.508
3.521
4.480
4.494
4.508
6.918
6.950
7.070
7.072
7.086
7.100
7.101
7.195
7.223
7.225
7.237
7.239
7.242
7.253
7.255
7.551
7.552
7.568
7.587
7.603
7.716
7.748
2.99
2.10
2.00
2.00
2.06
2.00
1.08
1.15
0.96
1.08
0.99
1.03
1.01
200 180 160 140 120 100 80 60 40 20 0 ppm
14.17
17.83
32.03
33.81
39.53
39.69
39.86
40.03
40.12
40.19
40.28
40.36
40.45
40.53
40.62
41.40
42.24
104.07
110.68
120.85
121.64
123.85
127.12
127.42
128.62
130.31
135.07
138.71
199.90
S40
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1w
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1w
11 10 9 8 7 6 5 4 3 2 1 0 ppm
1.796
1.802
1.808
2.502
2.506
2.510
2.513
2.517
3.333
3.519
3.531
3.544
4.433
4.446
7.087
7.092
7.105
7.110
7.124
7.129
7.381
7.386
7.401
7.406
7.464
7.582
7.586
7.597
7.613
7.623
7.633
7.642
7.674
7.677
7.679
7.688
7.691
7.695
7.704
7.706
7.708
7.873
7.904
8.004
8.034
8.170
8.172
8.187
4.12
2.05
2.06
1.00
0.99
0.98
3.04
1.03
1.02
1.04
1.99
200 180 160 140 120 100 80 60 40 20 0 ppm
29.58
30.03
34.92
39.53
39.70
39.87
40.03
40.20
40.29
40.37
40.53
42.41
104.46
104.50
105.65
105.83
112.25
112.33
112.55
123.32
127.56
127.65
128.94
129.31
132.00
133.65
135.69
136.98
138.02
157.07
158.93
188.94
S41
1H NMR (500 MHz, DMSO-d6) spectrum of compound 1x
13C NMR (125 MHz, DMSO-d6) spectrum of compound 1x
9 8 7 6 5 4 3 2 1 0 ppm
0.919
0.934
0.948
1.599
1.614
1.628
1.643
2.506
2.510
2.513
2.707
2.721
2.736
3.323
3.797
3.809
3.821
4.823
4.836
4.848
6.906
6.938
7.082
7.097
7.111
7.213
7.218
7.234
7.249
7.251
7.571
7.588
7.606
7.733
7.765
3.07
2.23
2.08
2.13
2.00
1.12
1.33
2.09
2.20
1.15
200 180 160 140 120 100 80 60 40 20 0 ppm
14.17
17.82
32.95
39.52
39.69
39.86
40.03
40.12
40.19
40.28
40.36
40.45
40.53
40.62
42.16
44.23
104.03
111.06
121.01
121.52
123.80
127.25
127.69
130.75
135.47
138.63
200.00
S42
1H NMR (500 MHz, DMSO-d6) spectrum of compound 3a
13C NMR (125 MHz, DMSO-d6) spectrum of compound 3a
8 7 6 5 4 3 2 1 0 ppm
2.511
3.329
3.758
3.770
3.782
4.537
4.550
4.562
6.255
7.122
7.127
7.213
7.545
7.560
7.575
7.589
7.630
7.645
7.659
7.720
7.750
8.090
8.105
2.26
2.00
1.05
0.92
0.91
3.06
1.12
1.12
1.96
200 180 160 140 120 100 80 60 40 20 0 ppm
33.69
39.53
39.70
39.87
40.03
40.20
40.29
40.37
40.46
40.53
47.85
110.35
113.78
116.88
128.49
128.61
129.15
129.67
132.28
133.08
138.64
188.83
S43
1H NMR (500 MHz, DMSO-d6) spectrum of compound 3b
13C NMR (125 MHz, DMSO-d6) spectrum of compound 3b
9 8 7 6 5 4 3 2 1 0 ppm
2.504
2.507
2.511
2.514
2.517
3.327
3.754
3.767
3.779
4.537
4.550
4.562
6.250
6.256
6.263
7.126
7.129
7.133
7.136
7.211
7.215
7.219
7.362
7.380
7.397
7.564
7.594
7.715
7.745
8.177
8.188
8.194
8.206
2.00
2.06
0.93
0.93
0.93
1.96
1.03
1.09
1.93
200 180 160 140 120 100 80 60 40 20 0 ppm
33.76
39.50
39.67
39.84
40.00
40.09
40.17
40.26
40.34
40.43
40.50
40.60
47.82
110.39
113.89
116.04
116.21
116.57
128.57
129.66
131.50
131.58
132.45
135.28
164.23
166.23
187.36
S44
1H NMR (500 MHz, DMSO-d6) spectrum of compound 3c
13C NMR (125 MHz, DMSO-d6) spectrum of compound 3c
10 9 8 7 6 5 4 3 2 1 0 ppm
2.506
2.510
2.514
3.351
3.751
3.764
3.776
4.539
4.551
4.563
6.258
6.264
6.265
6.271
7.180
7.183
7.188
7.191
7.224
7.229
7.232
7.497
7.512
7.528
7.553
7.583
7.745
7.775
7.810
7.812
7.814
7.815
7.826
7.827
7.830
7.831
8.089
8.105
8.231
8.234
2.08
2.08
0.98
0.99
1.03
1.01
1.01
1.07
0.98
1.06
1.00
7.37.47.57.67.77.8 ppm
200 180 160 140 120 100 80 60 40 20 0 ppm
33.72
36.70
39.53
39.70
39.86
40.03
40.20
40.29
40.37
40.53
47.85
110.51
114.37
116.31
122.73
127.61
128.87
129.69
131.13
131.33
133.00
135.65
140.70
187.40
S45
1H NMR (500 MHz, CDCl3) spectrum of compound 3d
13C NMR (125 MHz, CDCl3) spectrum of compound 3d
10 9 8 7 6 5 4 3 2 1 0 ppm
-0.000
1.642
3.591
3.604
3.618
4.461
4.474
4.488
6.315
6.321
6.328
6.982
6.990
6.994
7.265
7.300
7.330
7.684
7.700
7.716
7.821
7.850
8.333
8.349
8.404
8.406
8.408
8.420
8.422
8.424
8.822
1.98
2.00
1.03
1.96
1.16
1.03
1.05
0.98
1.00
0.94
200 180 160 140 120 100 80 60 40 20 0 ppm
30.64
48.45
76.78
77.03
77.28
110.88
114.15
115.61
123.03
126.75
128.21
129.12
129.81
132.84
133.87
140.01
148.45
187.03
S46
1H NMR (500 MHz, DMSO-d6) spectrum of compound 3e
13C NMR (125 MHz, DMSO-d6) spectrum of compound 3e
9 8 7 6 5 4 3 2 1 0 ppm
2.182
2.195
2.209
2.223
2.236
2.506
2.510
2.514
3.339
3.433
3.446
3.459
4.243
4.257
4.271
6.244
6.251
6.257
7.166
7.174
7.498
7.514
7.530
7.546
7.576
7.759
7.789
7.816
7.818
7.832
8.082
8.098
8.224
8.228
8.231
2.11
2.06
2.03
0.98
1.97
0.95
1.01
0.99
0.99
1.01
1.00
200 180 160 140 120 100 80 60 40 20 0 ppm
31.66
34.69
39.54
39.70
39.87
40.04
40.20
40.37
40.54
45.05
110.53
114.45
116.31
122.71
127.61
128.66
129.46
131.10
131.36
132.95
135.64
140.73
187.44
S47
1H NMR (500 MHz, DMSO-d6) spectrum of compound 3f
13C NMR (125 MHz, DMSO-d6) spectrum of compound 3f
9 8 7 6 5 4 3 2 1 0 ppm
2.183
2.196
2.210
2.223
2.236
2.502
2.505
2.509
2.513
2.516
3.346
3.430
3.443
3.456
4.245
4.260
4.273
6.252
6.257
6.259
6.264
7.149
7.152
7.157
7.160
7.175
7.180
7.183
7.547
7.577
7.778
7.808
7.889
7.905
8.248
8.264
2.09
2.14
2.07
0.96
2.01
0.97
1.06
2.08
2.00
200 180 160 140 120 100 80 60 40 20 0 ppm
31.61
34.68
39.52
39.69
39.86
40.02
40.19
40.28
40.36
40.45
40.53
45.05
110.61
114.45
116.48
121.11
123.28
125.45
126.01
126.04
126.07
127.61
128.83
129.10
129.33
129.42
132.03
132.29
132.54
132.79
133.25
141.99
188.15
S48
1H NMR (500 MHz, DMSO-d6) spectrum of compound 3g
13C NMR (125 MHz, DMSO-d6) spectrum of compound 3g
9 8 7 6 5 4 3 2 1 0 ppm
2.181
2.194
2.208
2.221
2.234
2.506
2.510
2.513
3.350
3.353
3.432
3.445
3.457
4.243
4.257
4.271
6.245
6.252
6.258
7.164
7.168
7.175
7.550
7.556
7.564
7.580
7.585
7.595
7.682
7.684
7.698
7.700
7.764
7.794
8.042
8.058
8.097
8.100
8.104
2.17
2.11
2.00
1.04
2.01
2.17
1.24
1.03
0.99
0.96
200 180 160 140 120 100 80 60 40 20 0 ppm
31.64
34.69
39.53
39.70
39.87
40.03
40.20
40.37
40.53
45.05
110.53
114.42
116.33
127.23
128.24
128.65
129.46
131.09
132.73
132.94
134.20
140.53
187.50
S49
1H NMR (500 MHz, DMSO-d6) spectrum of compound 3h
13C NMR (125 MHz, DMSO-d6) spectrum of compound 3h
9 8 7 6 5 4 3 2 1 0 ppm
2.184
2.197
2.211
2.224
2.237
2.508
2.511
2.514
3.350
3.437
3.449
3.462
3.836
3.845
3.859
3.868
4.237
4.250
4.264
6.224
6.230
6.237
7.077
7.094
7.101
7.116
7.120
7.559
7.569
7.584
7.587
7.600
7.709
7.739
7.807
7.811
7.824
7.828
2.05
2.06
6.05
2.00
1.10
3.36
2.05
1.01
1.09
200 180 160 140 120 100 80 60 40 20 0 ppm
31.71
34.68
39.53
39.69
39.86
40.03
40.12
40.19
40.28
40.36
40.45
40.53
45.03
56.06
56.22
110.16
111.19
111.38
113.43
117.00
123.16
127.83
129.53
131.32
131.51
149.19
153.29
187.21
S50
1H NMR (500 MHz, CDCl3) spectrum of compound 2a
13C NMR (125 MHz, CDCl3) spectrum of compound 2a
9 8 7 6 5 4 3 2 1 0 ppm
-0.000
2.598
2.612
2.625
2.639
2.652
4.245
4.258
4.272
4.625
4.639
4.652
7.162
7.176
7.192
7.256
7.257
7.314
7.329
7.331
7.345
7.372
7.389
7.498
7.514
7.529
7.588
7.604
7.623
7.736
7.752
8.303
8.318
8.319
2.02
2.08
2.00
0.95
0.96
1.04
2.00
1.92
1.00
1.94
200 180 160 140 120 100 80 60 40 20 0 ppm
28.92
40.75
46.60
76.79
77.05
77.30
109.00
109.78
120.62
122.42
124.10
124.95
127.60
128.31
130.74
133.08
134.75
137.23
138.15
143.74
186.25
S51
1H NMR (500 MHz, CDCl3) spectrum of compound 2b
13C NMR (125 MHz, CDCl3) spectrum of compound 2b
9 8 7 6 5 4 3 2 1 0 ppm
0.000
2.573
2.586
2.599
2.613
2.626
4.243
4.256
4.270
4.591
4.604
4.618
7.162
7.177
7.192
7.249
7.317
7.332
7.346
7.348
7.369
7.385
7.397
7.399
7.412
7.414
7.427
7.429
7.553
7.556
7.568
7.571
7.614
7.625
7.723
7.739
2.10
2.03
2.00
1.00
4.19
1.02
1.90
1.04
200 180 160 140 120 100 80 60 40 20 0 ppm
28.75
41.12
46.82
76.83
77.09
77.34
109.17
110.17
120.14
120.77
122.45
124.37
124.59
127.12
127.61
130.05
131.67
133.36
134.47
138.41
140.53
143.04
188.02
S52
1H NMR (500 MHz, CDCl3) spectrum of compound 2c
13C NMR (125 MHz, CDCl3) spectrum of compound 2c
9 8 7 6 5 4 3 2 1 0 ppm
0.000
2.519
2.533
2.546
2.559
2.572
4.160
4.173
4.186
4.541
4.555
4.568
7.089
7.103
7.118
7.178
7.242
7.257
7.272
7.293
7.309
7.547
7.567
7.584
7.662
7.678
8.142
8.159
2.06
2.10
2.06
1.01
2.19
3.05
1.00
2.06
200 180 160 140 120 100 80 60 40 20 0 ppm
-0.00
27.90
39.75
45.63
75.77
76.02
76.28
108.00
108.97
119.68
121.43
123.22
123.77
126.56
127.32
130.59
131.27
133.96
134.99
137.20
142.41
183.86
S53
1H NMR (500 MHz, DMSO-d6) spectrum of compound 2d
13C NMR (125 MHz, DMSO-d6) spectrum of compound 2d
9 8 7 6 5 4 3 2 1 0 ppm
2.512
2.544
2.558
2.571
2.584
3.336
4.375
4.387
4.400
4.657
4.670
4.684
7.147
7.162
7.304
7.319
7.334
7.460
7.619
7.635
7.651
7.694
7.711
7.729
7.745
7.770
7.785
8.094
8.109
8.175
2.26
2.08
2.00
1.06
1.03
1.00
1.02
3.07
0.96
0.92
200 180 160 140 120 100 80 60 40 20 0 ppm
28.62
39.51
39.68
39.85
40.01
40.10
40.18
40.27
40.35
40.43
40.51
41.17
47.35
108.79
110.73
120.72
122.00
124.12
125.12
127.13
129.23
130.47
130.89
133.27
133.57
134.85
138.41
139.43
143.04
185.08
S54
1H NMR (500 MHz, DMSO-d6) spectrum of compound 2e
13C NMR (125 MHz, DMSO-d6) spectrum of compound 2e
8 7 6 5 4 3 2 1 0 ppm
2.512
2.544
2.557
2.569
3.341
4.356
4.368
4.380
4.654
4.667
4.680
5.390
6.855
6.870
7.115
7.129
7.144
7.178
7.194
7.209
7.263
7.281
7.299
7.320
7.411
7.676
7.693
7.709
2.25
2.06
2.00
1.95
0.96
1.24
1.12
3.93
2.04
4.24.44.64.85.05.25.4 ppm
200 180 160 140 120 100 80 60 40 20 0 ppm
28.42
39.56
39.73
39.89
40.06
40.23
40.39
40.56
41.54
47.50
63.29
107.98
110.67
115.41
118.64
119.18
120.66
121.86
123.89
125.36
127.22
129.21
133.63
138.22
138.33
143.82
149.22
187.57
S55
1H NMR (500 MHz, CDCl3) spectrum of compound 2f
13C NMR (125 MHz, CDCl3) spectrum of compound 2f
9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
0.000
0.919
0.932
1.864
1.875
1.888
1.902
1.915
1.929
1.942
1.956
1.970
1.983
2.549
2.563
2.591
2.604
2.618
2.631
2.645
4.239
4.252
4.265
4.621
4.634
4.648
7.152
7.154
7.168
7.182
7.184
7.255
7.274
7.291
7.295
7.303
7.305
7.320
7.322
7.334
7.336
7.364
7.380
7.598
7.724
7.740
8.235
8.251
2.82
2.93
1.05
2.01
2.02
2.00
2.00
1.04
2.03
1.11
1.04
0.93
1.01
1.91
2.02.12.22.32.42.52.62.7 ppm
200 180 160 140 120 100 80 60 40 20 0 ppm
22.38
28.91
30.09
40.76
45.53
46.58
76.76
77.02
77.22
77.27
108.95
109.64
120.57
122.39
124.00
125.06
127.65
129.09
130.76
134.50
134.93
138.13
143.98
147.67
185.89
S56
1H NMR (500 MHz, CDCl3) spectrum of compound 2g
13C NMR (125 MHz, CDCl3) spectrum of compound 2g
9 8 7 6 5 4 3 2 1 0 ppm
0.006
2.584
2.598
2.611
2.625
2.638
4.237
4.250
4.263
4.613
4.626
4.640
7.072
7.073
7.077
7.088
7.090
7.093
7.118
7.158
7.174
7.188
7.258
7.313
7.330
7.346
7.363
7.378
7.588
7.726
7.742
7.787
7.790
7.794
7.851
7.866
2.03
2.02
2.00
1.04
1.07
1.36
1.93
0.93
0.97
0.96
1.04
200 180 160 140 120 100 80 60 40 20 0 ppm
-0.03
28.88
40.74
46.65
76.75
77.00
77.20
77.25
108.98
109.81
117.20
120.53
120.65
122.43
123.30
124.15
124.80
127.60
129.62
134.80
138.17
138.49
143.65
155.79
185.78
S57
1H NMR (500 MHz, DMSO-d6) spectrum of compound 2h
13C NMR (125 MHz, DMSO-d6) spectrum of compound 2h
9 8 7 6 5 4 3 2 1 0 ppm
2.505
2.508
2.512
2.515
2.533
2.546
2.559
3.321
3.642
3.840
4.339
4.352
4.365
4.616
4.629
4.642
6.595
6.599
6.629
6.633
6.646
6.650
7.103
7.104
7.118
7.133
7.184
7.274
7.276
7.291
7.293
7.305
7.307
7.515
7.532
7.645
7.661
7.667
7.684
2.10
3.00
3.00
2.04
2.04
0.94
1.06
1.00
0.97
1.03
1.00
2.03
200 180 160 140 120 100 80 60 40 20 0 ppm
33.19
44.32
44.48
44.65
44.82
44.99
45.07
45.15
45.32
46.38
52.07
60.81
60.96
103.94
110.54
112.49
115.48
125.48
126.43
126.71
128.62
130.17
131.99
137.20
137.45
143.01
149.75
165.34
168.90
191.55
S58
1H NMR (500 MHz, CDCl3) spectrum of compound 2i
13C NMR (125 MHz, CDCl3) spectrum of compound 2i
10 9 8 7 6 5 4 3 2 1 0 ppm
-0.000
2.605
2.618
2.631
2.645
2.658
2.782
4.247
4.260
4.273
4.628
4.642
4.656
7.168
7.182
7.185
7.198
7.202
7.257
7.319
7.321
7.336
7.338
7.350
7.351
7.375
7.391
7.618
7.741
7.757
8.393
8.397
8.403
8.410
8.417
8.421
2.03
2.01
2.00
2.95
1.01
1.06
0.96
0.98
1.95
200 180 160 140 120 100 80 60 40 20 0 ppm
-0.00
28.95
40.76
46.64
76.77
77.03
77.28
109.00
109.91
115.35
115.53
120.69
122.46
124.19
124.88
127.62
133.47
133.54
134.89
138.20
143.61
164.86
166.89
184.41
S59
1H NMR (500 MHz, DMSO-d6) spectrum of compound 2j
13C NMR (125 MHz, DMSO-d6) spectrum of compound 2j
11 10 9 8 7 6 5 4 3 2 1 0 ppm
2.087
2.505
2.508
2.512
2.537
2.550
2.564
2.577
2.590
3.348
4.357
4.370
4.383
4.656
4.669
4.683
7.117
7.132
7.146
7.286
7.301
7.315
7.403
7.479
7.495
7.511
7.671
7.688
7.704
7.720
7.823
7.839
7.922
7.938
8.355
10.192
3.09
2.04
2.05
2.00
1.08
1.08
1.07
1.09
2.15
1.10
1.04
0.97
1.05
200 180 160 140 120 100 80 60 40 20 0 ppm
24.45
28.51
39.56
39.73
39.89
40.06
40.23
40.39
40.56
41.42
47.46
108.45
110.67
120.68
120.94
121.93
124.00
124.08
125.24
125.64
127.21
129.17
134.28
138.02
138.38
139.88
143.40
169.07
186.56
S60
1H NMR (500 MHz, CDCl3) spectrum of compound 2k
13C NMR (125 MHz, CDCl3) spectrum of compound 2k
10 9 8 7 6 5 4 3 2 1 0 ppm
-0.000
2.617
2.631
2.644
2.658
2.671
4.260
4.273
4.286
4.640
4.653
4.667
7.178
7.181
7.192
7.194
7.196
7.208
7.210
7.255
7.334
7.336
7.348
7.351
7.353
7.364
7.367
7.385
7.386
7.401
7.402
7.662
7.663
7.747
7.755
7.771
7.787
8.422
8.438
2.00
2.02
2.00
1.07
1.07
1.17
1.01
3.04
1.92
200 180 160 140 120 100 80 60 40 20 0 ppm
-0.01
28.92
40.77
46.69
76.78
77.03
77.28
109.05
110.21
120.78
122.50
122.68
124.38
124.64
124.85
125.23
125.26
125.29
125.32
127.54
130.98
133.73
133.99
134.25
134.51
135.29
138.28
140.16
143.18
185.02
S61
1H NMR (500 MHz, CDCl3) spectrum of compound 2m
13C NMR (125 MHz, CDCl3) spectrum of compound 2m
9 8 7 6 5 4 3 2 1 0 ppm
0.000
2.431
2.579
2.592
2.606
2.619
2.632
4.227
4.240
4.254
4.607
4.620
4.634
7.149
7.163
7.178
7.252
7.298
7.314
7.328
7.356
7.373
7.601
7.721
7.737
8.214
8.231
3.03
2.00
2.05
2.02
1.06
2.91
1.10
0.92
1.00
1.90
200 180 160 140 120 100 80 60 40 20 0 ppm
21.72
28.91
40.79
46.60
76.80
77.05
77.31
108.98
109.65
120.58
122.38
124.02
125.06
127.64
129.04
130.89
134.51
134.71
138.14
143.94
143.96
185.88
S62
1H NMR (500 MHz, CDCl3) spectrum of compound 2n
13C NMR (125 MHz, CDCl3) spectrum of compound 2n
9 8 7 6 5 4 3 2 1 0 ppm
-0.000
2.631
2.644
2.658
2.672
2.685
4.245
4.258
4.271
4.658
4.672
4.685
7.086
7.091
7.104
7.109
7.122
7.127
7.260
7.302
7.310
7.320
7.328
7.385
7.390
7.403
7.408
7.606
7.776
7.793
8.425
8.441
2.13
2.16
2.00
1.14
1.18
1.10
1.01
2.20
2.04
200 180 160 140 120 100 80 60 40 20 0 ppm
-0.04
28.92
41.13
46.67
76.74
77.00
77.25
106.78
106.97
109.76
109.81
109.89
113.03
113.25
122.65
124.82
125.24
125.27
125.30
125.33
126.15
127.66
127.75
130.98
134.09
134.35
134.90
134.92
140.05
143.33
157.24
159.13
185.00
S63
1H NMR (500 MHz, CDCl3) spectrum of compound 2o
13C NMR (125 MHz, CDCl3) spectrum of compound 2o
11 10 9 8 7 6 5 4 3 2 1 0 ppm
-0.000
2.612
2.625
2.639
2.652
2.666
4.253
4.267
4.280
4.636
4.649
4.663
7.172
7.173
7.187
7.201
7.203
7.218
7.258
7.327
7.328
7.343
7.345
7.357
7.359
7.378
7.394
7.410
7.627
7.713
7.715
7.717
7.719
7.729
7.731
7.733
7.735
7.746
7.762
8.275
8.291
8.457
8.461
8.464
2.02
2.02
2.00
1.09
1.16
2.09
0.91
2.04
0.97
0.87
200 180 160 140 120 100 80 60 40 20 0 ppm
28.93
40.73
46.66
76.78
77.04
77.24
77.29
109.04
110.04
120.72
122.48
122.52
124.28
124.70
127.54
129.35
129.89
133.61
135.10
135.87
138.22
138.95
143.23
184.57
S64
1H NMR (500 MHz, CDCl3) spectrum of compound 2p
13C NMR (125 MHz, CDCl3) spectrum of compound 2p
9 8 7 6 5 4 3 2 1 0 ppm
-0.000
4.524
4.535
4.547
4.914
4.926
4.937
7.189
7.197
7.205
7.213
7.221
7.230
7.257
7.363
7.370
7.396
7.411
7.427
7.725
7.741
7.760
7.776
8.084
8.351
8.366
8.521
2.02
2.00
1.19
1.97
1.39
2.37
0.99
1.02
0.94
200 180 160 140 120 100 80 60 40 20 0 ppm
39.85
45.38
76.76
77.01
77.27
108.87
109.26
121.24
122.50
122.90
123.44
125.03
128.35
129.29
129.84
133.02
133.47
135.68
137.39
139.24
141.33
184.47
S65
1H NMR (500 MHz, CDCl3 + DMSO-d6) spectrum of compound 2q
13C NMR (125 MHz, CDCl3 + DMSO-d6)) spectrum of compound 2q
10 9 8 7 6 5 4 3 2 1 0 ppm
-0.000
0.922
0.926
0.938
0.945
0.951
1.910
1.923
1.936
1.950
1.963
1.977
2.555
2.558
2.569
2.584
3.141
4.538
4.550
4.562
4.923
4.935
4.947
7.171
7.173
7.185
7.187
7.200
7.203
7.305
7.318
7.322
7.334
7.349
7.362
7.364
7.373
7.389
7.735
7.751
8.011
8.023
8.027
8.034
8.041
8.285
8.289
8.301
8.318
6.17
1.06
2.06
2.00
1.98
1.01
4.41
1.00
0.96
1.95
200 180 160 140 120 100 80 60 40 20 0 ppm
22.44
30.03
39.66
39.83
39.99
40.16
40.33
40.50
40.66
45.34
45.46
78.01
78.27
78.53
107.53
109.92
120.96
122.32
123.85
124.59
128.07
129.03
130.58
132.49
135.26
137.34
141.58
147.27
185.62
S66
1H NMR (500 MHz, CDCl3) spectrum of compound 2r
13C NMR (125 MHz, CDCl3) spectrum of compound 2r
11 10 9 8 7 6 5 4 3 2 1 0 ppm
-0.000
4.527
4.539
4.551
4.917
4.930
4.941
7.189
7.196
7.204
7.212
7.220
7.257
7.353
7.362
7.370
7.458
7.474
7.489
7.569
7.572
7.574
7.576
7.585
7.588
7.590
7.592
7.760
7.776
8.087
8.301
8.303
8.314
8.316
8.373
8.376
8.380
2.14
2.12
1.11
2.07
1.18
1.05
1.07
1.00
1.04
1.00
180 160 140 120 100 80 60 40 20 0 ppm
39.84
45.37
76.76
77.02
77.27
108.85
109.26
121.23
122.88
123.45
125.02
128.35
128.83
129.57
130.59
132.75
133.00
134.49
137.39
139.03
141.36
184.54
S67
1H NMR (500 MHz, DMSO-d6) spectrum of compound 2s
13C NMR (125 MHz, DMSO-d6) spectrum of compound 2s
9 8 7 6 5 4 3 2 1 0 ppm
2.501
2.504
2.508
2.511
2.515
3.323
3.734
3.876
4.652
4.664
4.676
4.975
4.988
5.000
6.654
6.659
6.671
6.675
6.719
6.723
7.145
7.146
7.160
7.175
7.325
7.327
7.342
7.356
7.358
7.486
7.503
7.646
7.662
7.754
7.770
7.794
3.00
3.00
2.03
2.02
1.00
1.01
1.03
1.04
1.01
1.03
1.01
0.94
200 180 160 140 120 100 80 60 40 20 0 ppm
39.56
39.72
39.89
40.06
40.22
40.39
40.48
40.56
45.43
56.04
56.27
99.40
105.58
106.32
110.92
121.06
122.28
122.37
124.29
124.58
127.92
131.07
131.99
137.49
142.33
160.09
163.57
187.19
S68
1H NMR (500 MHz, CDCl3 + DMSO-d6) spectrum of compound 2t
13C NMR (125 MHz, CDCl3 + DMSO-d6) spectrum of compound 2t
9 8 7 6 5 4 3 2 1 0 ppm
-0.000
4.501
4.511
4.524
4.871
4.879
4.889
4.901
7.091
7.107
7.123
7.128
7.135
7.154
7.169
7.184
7.295
7.301
7.313
7.317
7.328
7.349
7.365
7.695
7.715
7.731
7.805
7.824
7.842
7.863
7.985
7.989
8.006
2.00
2.01
2.13
3.28
1.00
2.03
0.99
200 180 160 140 120 100 80 60 40 20 0 ppm
44.38
44.55
44.64
44.71
44.88
45.05
45.21
45.38
50.16
82.81
83.07
83.33
112.24
114.69
121.99
125.04
125.65
126.28
126.98
128.58
129.35
132.79
134.01
137.27
142.07
143.52
146.27
162.22
190.67
S69
1H NMR (500 MHz, CDCl3) spectrum of compound 2u
13C NMR (125 MHz, CDCl3) spectrum of compound 2u
10 9 8 7 6 5 4 3 2 1 0 ppm
-0.000
4.513
4.525
4.538
4.902
4.915
4.927
7.178
7.185
7.186
7.194
7.202
7.210
7.254
7.350
7.358
7.521
7.524
7.536
7.551
7.597
7.600
7.602
7.611
7.614
7.619
7.627
7.629
7.632
7.750
7.766
8.087
8.367
8.370
8.373
8.384
8.386
2.03
2.00
1.08
2.03
2.05
1.08
1.06
0.94
1.94
200 180 160 140 120 100 80 60 40 20 0 ppm
39.86
45.38
76.79
77.05
77.30
108.57
109.26
121.15
122.83
123.63
124.86
128.33
128.36
130.65
132.76
132.92
137.30
137.50
141.75
186.27
S70
1H NMR (500 MHz, DMSO-d6) spectrum of compound 2v
13C NMR (125 MHz, DMSO-d6) spectrum of compound 2v
8 7 6 5 4 3 2 1 0 ppm
0.948
0.963
0.978
1.663
1.677
1.692
1.706
1.721
1.735
2.513
2.525
2.539
3.114
3.128
3.142
3.328
4.296
4.309
4.322
4.587
4.600
4.613
7.123
7.138
7.153
7.288
7.303
7.318
7.424
7.665
7.681
7.710
7.725
3.08
2.10
2.15
2.05
2.00
2.08
0.96
1.01
0.91
2.01
200 180 160 140 120 100 80 60 40 20 0 ppm
14.15
17.55
28.55
39.53
39.70
39.87
40.03
40.20
40.37
40.53
41.26
41.97
47.21
108.80
110.68
120.67
121.91
123.99
125.22
127.12
132.43
138.33
143.33
194.69
S71
1H NMR (500 MHz, DMSO-d6) spectrum of compound 2x
13C NMR (125 MHz, DMSO-d6) spectrum of compound 2x
8 7 6 5 4 3 2 1 0 ppm
0.970
0.984
0.999
1.727
1.742
1.756
1.771
2.509
3.141
3.156
3.170
3.324
4.623
4.635
4.647
4.964
4.976
4.988
7.138
7.152
7.168
7.318
7.333
7.348
7.627
7.644
7.750
7.766
7.839
3.09
2.17
2.12
2.03
2.00
1.09
1.15
1.05
1.05
1.03
200 180 160 140 120 100 80 60 40 20 0 ppm
14.19
17.73
39.52
39.69
39.85
40.02
40.19
40.35
40.52
41.53
45.47
106.66
110.95
121.07
122.41
124.12
124.63
127.87
130.29
137.51
141.43
194.82
S72
1H NMR (500 MHz, DMSO-d6) spectrum of compound 4a
13C NMR (125 MHz, DMSO-d6) spectrum of compound 4a
9 8 7 6 5 4 3 2 1 0 ppm
2.506
2.509
2.513
2.636
3.351
4.488
4.500
4.513
4.835
4.848
4.860
6.316
6.321
6.323
6.329
7.265
7.268
7.272
7.442
7.445
7.449
7.452
7.571
7.586
7.602
7.665
7.680
7.695
8.215
8.217
8.232
2.02
2.01
1.02
1.04
1.06
2.06
1.06
2.00
200 180 160 140 120 100 80 60 40 20 0 ppm
39.49
39.66
39.83
40.00
40.08
40.16
40.25
40.33
40.42
40.50
43.41
45.34
109.97
114.47
118.54
126.01
128.74
130.53
133.11
133.19
138.01
139.25
185.89
S73
1H NMR (500 MHz, CDCl3) spectrum of compound 4b
13C NMR (125 MHz, CDCl3) spectrum of compound 4b
10 9 8 7 6 5 4 3 2 1 0 ppm
4.397
4.409
4.422
4.776
4.788
4.800
6.370
6.375
6.378
6.383
6.933
6.936
6.938
6.941
7.164
7.170
7.174
7.187
7.201
7.205
7.210
7.222
7.262
7.302
7.640
7.643
7.648
7.650
8.417
8.422
8.427
8.433
8.440
8.447
8.451
8.457
2.08
2.00
1.01
1.00
2.06
0.97
2.00
200 180 160 140 120 100 80 60 40 20 0 ppm
43.58
45.14
76.77
77.02
77.22
77.28
110.82
115.21
115.38
115.63
118.82
124.49
133.19
133.21
133.26
133.93
133.96
139.78
164.58
166.60
184.33
S74
1H NMR (500 MHz, DMSO-d6) spectrum of compound 4c
13C NMR (125 MHz, DMSO-d6) spectrum of compound 4c
9 8 7 6 5 4 3 2 1 0 ppm
1.995
2.509
3.320
4.506
4.518
4.530
4.860
4.872
4.884
6.345
6.352
6.358
7.301
7.493
7.498
7.888
7.904
7.920
8.516
8.530
8.532
8.645
8.660
9.070
2.04
2.00
1.07
1.06
1.16
1.15
1.05
1.18
0.96
200 180 160 140 120 100 80 60 40 20 0 ppm
39.59
39.76
39.93
40.09
40.26
40.35
40.43
40.52
40.59
43.44
45.42
110.16
114.93
118.38
125.20
126.41
127.40
130.62
133.68
136.55
138.75
139.05
148.12
183.31
S75
1H NMR (500 MHz, CDCl3) spectrum of compound 4d
13C NMR (125 MHz, CDCl3) spectrum of compound 4d
9 8 7 6 5 4 3 2 1 0 ppm
0.000
4.397
4.409
4.422
4.779
4.792
4.804
6.372
6.377
6.379
6.385
6.933
6.936
6.937
6.940
7.261
7.503
7.518
7.533
7.578
7.580
7.593
7.605
7.607
7.651
7.654
7.659
7.662
8.325
8.328
8.342
2.00
2.01
0.95
0.95
1.11
1.03
0.94
1.93
200 180 160 140 120 100 80 60 40 20 0 ppm
43.59
45.14
76.78
77.04
77.24
77.29
110.78
115.50
118.87
124.43
128.22
130.49
132.62
133.10
137.71
139.91
186.22
S76
1H NMR (500 MHz, CDCl3) spectrum of compound 4e
13C NMR (125 MHz, CDCl3) spectrum of compound 4e
9 8 7 6 5 4 3 2 1 0 ppm
2.546
2.559
2.572
2.586
2.600
4.079
4.092
4.106
4.571
4.585
4.598
6.305
6.311
6.318
6.917
6.921
6.925
7.261
7.300
7.302
7.335
7.359
7.375
7.391
7.693
7.694
7.696
7.708
7.710
7.712
8.235
8.251
8.418
2.06
2.00
2.00
1.01
1.05
1.16
1.14
1.13
1.02
0.96
200 180 160 140 120 100 80 60 40 20 0 ppm
29.48
45.12
46.38
76.75
77.00
77.20
77.25
109.28
117.44
118.51
122.40
126.09
129.24
129.75
133.50
135.55
139.30
142.01
184.56
S77
1H NMR (500 MHz, CDCl3) spectrum of compound 4f
13C NMR (125 MHz, CDCl3) spectrum of compound 4f
9 8 7 6 5 4 3 2 1 0 ppm
2.553
2.567
2.580
2.594
2.607
4.089
4.102
4.115
4.577
4.590
4.604
6.320
6.325
6.328
6.333
6.929
6.933
6.934
6.938
7.262
7.295
7.298
7.302
7.306
7.751
7.768
8.378
8.394
2.09
2.05
2.00
0.95
0.98
1.01
2.08
1.94
200 180 160 140 120 100 80 60 40 20 0 ppm
29.47
45.14
46.42
76.75
77.00
77.21
77.26
109.33
117.61
118.45
120.55
122.72
124.89
125.11
125.14
125.17
125.20
126.23
127.05
130.86
133.47
133.72
133.98
134.24
135.71
140.49
141.96
185.01
S78
1H NMR (500 MHz, CDCl3) spectrum of compound 4g
13C NMR (125 MHz, CDCl3) spectrum of compound 4g
9 8 7 6 5 4 3 2 1 0 ppm
2.544
2.557
2.571
2.584
2.598
4.077
4.091
4.104
4.569
4.583
4.596
6.304
6.309
6.311
6.317
6.916
6.920
6.923
7.261
7.420
7.435
7.451
7.539
7.541
7.555
7.557
8.185
8.201
8.267
8.270
8.273
2.04
2.02
2.00
0.94
0.98
1.02
1.02
0.95
0.95
0.91
200 180 160 140 120 100 80 60 40 20 0 ppm
29.48
45.12
46.39
76.76
77.01
77.21
77.26
109.27
117.42
118.51
126.08
128.79
129.48
130.61
132.63
134.39
135.51
139.10
142.04
184.66
S79
1H NMR (500 MHz, CDCl3) spectrum of compound 4h
13C NMR (125 MHz, CDCl3) spectrum of compound 4h
9 8 7 6 5 4 3 2 1 0 ppm
-0.000
2.532
2.545
2.558
2.572
2.585
3.962
3.965
4.067
4.081
4.094
4.562
4.575
4.589
6.283
6.289
6.295
6.896
6.940
6.957
7.215
7.222
7.266
7.870
8.128
8.145
2.07
6.39
2.05
2.00
0.98
0.97
1.11
0.97
0.99
1.00
200 180 160 140 120 100 80 60 40 20 0 ppm
29.51
45.09
46.33
55.99
56.06
76.77
77.03
77.28
109.13
110.07
112.55
116.97
118.80
125.64
126.23
130.36
134.97
142.83
148.80
153.35
184.49
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