quinoxaline, 2-phenoxy-pyridine derivatives by aryne ...

An efficient synthesis of 4-phenoxy-quinazoline, 2-phenoxy-quinoxaline, 2-phenoxy-pyridine derivatives by aryne chemistry,

Mahesh K. Zilla,a,b# Sheena Mahajan,b,c# Rajni Khajuria,d Vivek K. Gupta,e Kamal K. Kapoorc,

and Asif Ali,b,f,*

aDepartment of Chemistry, Indian Institute of Science education and Research,

Berhampur, Odisha 760010, India.E-mail: [email protected] Institute of Integrative Medicine, Canal Road, Jammu-180001, India.cDepartment of Chemistry, University of Jammu, Jammu Tawi- 180006, India.

E-mail: [email protected], [email protected]. dDepartment of Chemistry, GCW Kathua, Jammu Tawi- 18000, India. E-mail:

[email protected] Department of Physics & Electronics, University of Jammu, Jammu Tawi-

180006, India. E-mail: [email protected] Knowledge Digital Library (TKDL), 14-Satsang Vihar, Vigyan Suchna

Bhawan, New Delhi-110067, India. E-mail : [email protected]

Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2021

mailto:[email protected]

mailto:[email protected],%[email protected]




General procedure for the preparation of 4-Phenoxy-2-arylquinazoline(3a-e) with aryne

4-Phenoxy-2-phenylquinazoline (3a)

4-Phenoxy-2-(3,4,5-trimethoxyphenyl)quinazoline (3b)

2-(4-(Methylthio)phenyl)-4-phenoxyquinazoline (3c)

4-Phenoxy-2-(4-(trifluoromethoxy)phenyl)quinazoline (3d)

4-Phenoxy-2-(4-(trifluoromethyl)phenyl)quinazoline (3e)

General procedure for the preparation of (E)-2-Phenoxy-3-styrylquinoxaline (5a-e) with

aryne

(E)-2-(4-Methoxystyryl)-3-phenoxyquinoxaline (5a)

(E)-3-(4-Methoxystyryl)-1-phenylquinoxalin-2(1H)-one (6a)

(E)-2-Phenoxy-3-(3,4,5-trimethoxystyryl)quinoxaline (5b)

(E)-1-Phenyl-3-(3,4,5-trimethoxystyryl)quinoxalin-2(1H)-one (6b)

2-((E)-2-(Benzo[d][1,3]dioxol-5-yl)vinyl)-3-phenoxyquinoxaline (5c)

(E)-3-(2-(Benzo[d][1,3]dioxol-5-yl)vinyl)-1-phenylquinoxalin-2(1H)-one (6c)

(E)-2-Phenoxy-3-(4-(trifluoromethyl)styryl)quinoxaline (5d)

(E)-1-Phenyl-3-(4-(trifluoromethyl)styryl)quinoxalin-2(1H)-one (6d)

(E)-2-(2-Chlorostyryl)-3-phenoxyquinoxaline (5e)

(E)-3-(2-Chlorostyryl)-1-phenylquinoxalin-2(1H)-one (6e)

General procedure for the preparation of 2-phenoxy pyridine derivatives (8a-f) with aryne

2-Phenoxy-6-phenyl-4-(3,4,5-trimethoxyphenyl)pyridine (8a)

2-(4-Methoxyphenyl)-6-phenoxy-4-(3,4,5-trimethoxyphenyl)pyridine (8b)

4-(3-Nitrophenyl)-2-phenoxy-6-phenylpyridine (8c)

4-(4-Bromophenyl)-2-(4-chlorophenyl)-6-phenoxypyridine (8d)

6-Phenoxy-4-phenyl-2, 2ꞌ-bipyridine (8e)

4-(Furan-2-yl)-2-phenoxy-6-phenylpyridine (8f)

General procedure for the preparation of 4-Phenoxy-2-arylquinazoline(3a-e) with aryne:

To a stirred solution of 2-phenylquinazolin-4(3H)-one (1a-e) (0.45mmol, 1.0 equiv) and

trimethylsilyl phenyl triflate (2) (0.54mmol, 1.2 equiv) in acetonitrile as solvent, was added

cesium fluoride (1.35mmol, 3.0 equiv) at room temperature. The mixture was stirred at

room temperature for 4hr, after completing the reaction, reaction mixture was concentrated

in vacuo. To the resulting residue, water was added, and the mixture was extracted with

ethyl acetate three times. The combined organic phase was dried over sodium sulphate, and

concentrated in vacuo. The crude product was purified by column chromatography (EtOAc in

Hexane) resulting the product.

4-Phenoxy-2-phenylquinazoline (3a).1H NMR (400 MHz, CDCl3): δ 8.25

(d, J = 7.7 Hz, 3H), 7.94 (d, J = 8.4 Hz, 1H), 7.75 (dd, J = 11.3, 4.0 Hz, 1H),

7.47 (t, J = 7.6 Hz, 1H), 7.39 (t, J = 7.8 Hz, 2H), 7.26 (ddd, J = 19.9, 10.0,

4.5 Hz, 6H); 13C NMR (101 MHz, CDCl3) δ 167.51, 160.71, 153.53,

153.49, 138.51, 134.77, 131.38, 130.25, 129.28, 129.19, 128.97,

127.64, 126.35, 124.39, 122.85, 115.94; IR: 3387, 3064, 2850, 1622, 1573, 1484, 1347, 1210,

933, 770 cm-1; HRMS-ESI [M+H]+m/z calcd for C20H15N2O: 299.1179, found 299.1176.

4-Phenoxy-2-(3,4,5-trimethoxyphenyl)quinazoline (3b).1H NMR

(400 MHz, CDCl3): δ 8.25 (d, J = 7.9 Hz, 1H), 7.95 (d, J = 8.4 Hz,

1H), 7.79 (dd, J = 11.2, 4.1 Hz, 1H), 7.55 (s, 2H), 7.49 (t, J = 7.5 Hz,

1H), 7.39 (t, J = 7.8 Hz, 2H), 7.28 (d, J = 7.7 Hz, 2H), 7.22 (t, J = 7.3

Hz, 1H), 3.79 (s, 3H), 3.76 (s, 6H); 13C NMR (101 MHz, CDCl3): δ

166.61, 159.11, 153.07, 152.84, 152.74, 140.40, 133.97, 132.90,

129.21, 128.05, 126.74, 125.50, 123.53, 122.40, 114.81, 105.49, 60.88, 55.91; IR: 3352, 2581,

1622, 1575, 1398, 1268, 1165, 1126, 767 cm-1; HRMS-ESI [M+H]+m/z calcd for C23H21N2O4:

389.1496, found 389.1506.

2-(4-(Methylthio)phenyl)-4-phenoxyquinazoline (3c).1H NMR

(400 MHz, CDCl3): δ 8.41 (d, J = 8.4 Hz, 2H), 8.03 (d, J = 8.1 Hz,

1H), 7.86 (d, J = 8.4 Hz, 1H), 7.70 (t, J = 7.4 Hz, 1H), 7.43 – 7.29

(m, 5H), 7.28 – 7.17 (m, 3H), 4.15 (s, 3H); 13C NMR (101 MHz,

CDCl3): δ 167.05, 159.44, 151.81, 139.46, 136.62, 134.81,

133.50, 132.00, 129.84, 129.34, 129.16, 127.92, 127.58, 126.43, 123.46, 115.29, 54.05; IR:

N

N

O

N

N

O

OCH3

OCH3

OCH3

N

N

O

SCH3

3361, 2922, 1621, 1576, 1502, 1452, 1348, 1175, 799, 690 cm-1; HRMS-ESI [M+H]+m/z calcd

for C21H17N2OS: 355.1624, found 355.1628.

4-Phenoxy-2-(4-(trifluoromethoxy)phenyl)quinazoline (3d). 1H

NMR (400 MHz, CDCl3): δ 8.24 (t, J = 7.5 Hz, 3H), 7.91 (d, J = 8.4

Hz, 1H), 7.76 (dd, J = 11.2, 4.0 Hz, 1H), 7.47 (t, J = 7.5 Hz, 1H),

7.42 – 7.36 (m, 2H), 7.28 – 7.19 (m, 3H), 7.11 (d, J = 8.5 Hz, 2H): 13C NMR (101 MHz, CDCl3): δ 166.83, 158.56, 152.66, 152.57,

151.07, 136.26, 134.10, 130.10, 129.51, 128.17, 127.09, 125.70, 123.62, 122.03, 120.47,

115.10; IR: 3392, 2921, 1607, 1562, 1486, 1162, 861, 742 cm-1;HRMS-ESI [M+H]+m/z calcd for

C21H14F3N2O2: 383.1002, found 383.1004.

4-Phenoxy-2-(4-(trifluoromethyl)phenyl)quinazoline (3e). 1H

NMR (400 MHz, CDCl3): δ 8.34 (d, J = 8.1 Hz, 2H), 8.28 (d, J = 8.1

Hz, 1H), 7.96 (d, J = 8.4 Hz, 1H), 7.81 (t, J = 7.7 Hz, 1H), 7.54 (t, J =

7.8 Hz, 3H), 7.42 (t, J = 7.8 Hz, 2H), 7.30 – 7.24 (m, 3H); 13C NMR

(101 MHz, CDCl3): δ 167.76, 159.26, 153.46, 153.36, 141.82,

135.04, 130.35, 129.52, 129.15, 128.26, 126.58, 126.13, 126.10, 124.49, 122.83, 116.16; IR:

3387, 2921, 2350, 1744, 1622, 1324, 1111, 690 cm-1;HRMS-ESI [M+H]+m/z calcd for

C21H14F3N2O: 367.1053, found 367.1055.

General procedure for the preparation of (E)-2-Phenoxy-3-styrylquinoxaline(5a-e) with

aryne:

To a stirred solution of (E)-3-styrylquinoxalin-2(1H)-one(4a-e) (0.28mmol, 1.0 equiv) and


Cesium fluoride (1.35mmol, 3.0 equiv) at room temperature. The mixture was stirred at




concentrated in vacuo. The crude product was purified by column chromatography (EtoAc in

Hexane), resulting the product.

(E)-2-(4-Methoxystyryl)-3-phenoxyquinoxaline (5a).1H NMR

(400 MHz, CDCl3): δ 8.04 (d, J = 16.0 Hz, 1H), 7.96 – 7.91 (m,

N

N

O

OCF3

N

N O

O

N

N

O

CF3

1H), 7.62 – 7.54 (m, 4H), 7.52 – 7.44 (m, 2H), 7.40 (t, J = 7.8 Hz, 2H), 7.21 (dd, J = 13.1, 11.1

Hz, 3H), 6.86 (d, J = 8.6 Hz, 2H), 3.77 (s, 3H).13C NMR (101 MHz, CDCl3): δ 160.58, 155.15,

153.11, 144.33, 139.95, 139.30, 137.27, 129.59, 129.37, 129.29, 129.04, 128.38, 127.52,

127.28, 125.28, 121.86, 118.65, 114.30, 55.38.IR: 3361, 2922, 1621, 1576, 1502, 1452, 1348,

1175, 799, 690 cm-1; HRMS-ESI [M+H]+m/z calcd for C23H19N2O2: 355.1441, found 355.1447.

(E)-3-(4-Methoxystyryl)-1-phenylquinoxalin-2(1H)-one

(6a).1H NMR (400 MHz, CDCl3): δ 8.13 (d, J = 16.2 Hz, 1H),

7.84 – 7.78 (m, 1H), 7.59 – 7.45 (m, 6H), 7.28 – 7.16 (m, 4H),

6.84 (d, J = 8.6 Hz, 2H), 6.57 (d, J = 8.1 Hz, 1H), 3.76 (s, 3H).13C

NMR (101 MHz, CDCl3): δ 160.73, 154.93, 153.36, 138.57,

136.13, 133.64, 133.43, 130.31, 129.50, 129.41, 129.40,

129.32, 129.07, 128.30, 124.00, 120.27, 115.40, 114.31, 55.37.IR: 3361, 2922, 1621, 1576,

1502, 1452, 1348, 1175, 799, 690 cm-1;HRMS-ESI [M+H]+m/z calcd for C23H19N2O2: 355.1441,

found 355.1435.

(E)-2-Phenoxy-3-(3,4,5-trimethoxystyryl)quinoxaline

(5b).1H NMR (400 MHz, CDCl3): δ 8.11 (d, J = 16.0 Hz, 1H),

8.02 (dd, J = 7.8, 1.7 Hz, 1H), 7.70 – 7.62 (m, 2H), 7.57 (ddd,

J = 7.6, 5.2, 1.8 Hz, 2H), 7.52 – 7.47 (m, 2H), 7.35 – 7.29 (m,

3H), 6.94 (s, 2H), 3.94 (s, 6H), 3.91 (s, 3H).13C NMR (126

MHz, CDCl3): δ 155.25, 153.46, 152.99, 143.81, 139.87,

139.40, 139.22, 137.73, 132.13, 129.68, 129.37, 128.41, 127.65, 127.30, 125.45, 122.01,

120.37, 104.83, 61.04, 56.23.IR: 3361, 2922, 1621, 1576, 1502, 1452, 1348, 1175, 799, 690

cm-1;HRMS-ESI [M+H]+m/z calcd for C25H23N2O4: 415.1652, found 415.1653.

(E)-1-Phenyl-3-(3,4,5-trimethoxystyryl)quinoxalin-2(1H)-

one (6b).1H NMR (400 MHz, CDCl3): δ 8.21 (d, J = 16.1 Hz,

1H), 7.92 – 7.87 (m, 1H), 7.67 – 7.54 (m, 4H), 7.36 – 7.27

(m, 4H), 6.90 (s, 2H), 6.67 (dd, J = 7.8, 1.8 Hz, 1H), 3.90 (s,

6H), 3.89 (s, 3H).13C NMR (126 MHz, CDCl3): δ 154.92,

153.38, 152.89, 139.28, 139.01, 135.98, 133.62, 133.37,

132.14, 130.34, 129.49, 129.46, 129.40, 128.23, 124.16, 122.00, 115.49, 104.88, 61.01,

56.11.IR: 3361, 2922, 1621, 1576, 1502, 1452, 1348, 1175, 799, 690 cm-1;HRMS-ESI

[M+H]+m/z calcd for C25H23N2O4: 415.1652, found 415.1606.

N

N O

O

N

N O

OCH3

OCH3OCH3

N

N O

OCH3

OCH3

OCH3

2-((E)-2-(Benzo[d][1,3]dioxol-5-yl)vinyl)-3-

phenoxyquinoxaline (5c).1H NMR (400 MHz, CDCl3): δ 8.11

(d, J = 15.9 Hz, 1H), 8.05 (dd, J = 7.8, 1.4 Hz, 1H), 7.70 (dd, J =

7.8, 1.5 Hz, 1H), 7.64 (d, J = 16.0 Hz, 1H), 7.59 (td, J = 7.3, 1.6

Hz, 2H), 7.52 (t, J = 7.9 Hz, 2H), 7.36 – 7.31 (m, 3H), 7.29 (s,

1H), 7.20 (d, J = 8.0 Hz, 1H), 6.88 (d, J = 8.0 Hz, 1H), 6.03 (s, 2H).13C NMR (101 MHz, CDCl3): δ

155.14, 153.04, 148.72, 148.33, 144.09, 139.91, 139.35, 137.29, 131.08, 129.62, 129.16,

128.41, 127.58, 127.29, 125.33, 123.73, 121.87, 119.02, 108.58, 106.40, 101.42.IR: 3361,

2922, 1621, 1576, 1502, 1452, 1348, 1175, 799, 690 cm-1;HRMS-ESI [M+H]+m/z calcd for

C23H17N2O3: 369.1234, found 369.1243.

(E)-3-(2-(Benzo[d][1,3]dioxol-5-yl)vinyl)-1-phenylquinoxalin-

2(1H)-one (6c). 1H NMR (400 MHz, CDCl3): δ 8.19 (d, J = 16.1

Hz, 1H), 7.94 – 7.88 (m, 1H), 7.66 (t, J = 7.4 Hz, 2H), 7.59 (t, J =

12.0 Hz, 2H), 7.33 (t, J = 7.1 Hz, 3H), 7.26 (d, J = 20.9 Hz, 2H),

7.15 (d, J = 8.1 Hz, 1H), 6.85 (d, J = 8.0 Hz, 1H), 6.68 (d, J = 7.7

Hz, 1H), 6.03 (s, 2H).13C NMR (101 MHz, CDCl3): δ 154.91, 153.17, 148.87, 148.29, 138.61,

136.07, 133.65, 133.39, 131.14, 130.34, 129.46, 129.36, 129.20, 128.27, 124.07, 124.05,

120.70, 115.42, 108.56, 106.44, 101.40.IR: 3361, 2922, 1621, 1576, 1502, 1452, 1348, 1175,

799, 690 cm-1;HRMS-ESI [M+H]+m/z calcd for C23H17N2O3: 369.1234, found 369.1237.

(E)-2-Phenoxy-3-(4-

(trifluoromethyl)styryl)quinoxaline(5d).1H NMR (400 MHz,

CDCl3): δ 8.10 (d, J = 16.1 Hz, 1H), 8.01 – 7.96 (m, 1H), 7.77

(dd, J = 21.8, 12.1 Hz, 3H), 7.63 (ddd, J = 15.1, 8.5, 5.1 Hz, 3H),

7.56 – 7.50 (m, 2H), 7.46 – 7.40 (m, 2H), 7.29 – 7.18 (m,

3H).13C NMR (126 MHz, CDCl3): δ 155.26, 152.88, 143.17,

139.88, 139.83, 139.74, 135.70, 129.84, 129.68, 128.66, 127.83, 127.79, 127.37, 125.80,

125.77, 125.49, 123.38, 121.87.IR: 3361, 2922, 1621, 1576, 1502, 1452, 1348, 1175, 799, 690

cm-1;HRMS-ESI [M+H]+m/z calcd for C23H16F3N2O: 393.1209, found 393.1225.

(E)-1-Phenyl-3-(4-(trifluoromethyl)styryl)quinoxalin-2(1H)-

one (6d).1H NMR (500 MHz, CDCl3): δ 8.17 (d, J = 16.2 Hz,

1H), 7.87 – 7.82 (m, 1H), 7.68 (dd, J = 14.2, 12.3 Hz, 3H), 7.56

(dd, J = 10.1, 4.7 Hz, 4H), 7.51 (d, J= 7.5 Hz, 1H), 7.28 – 7.21

N

N

O

O

O

N

N O

O

O

N

N O

CF3

N

N O

CF3

(m, 4H), 6.62 – 6.57 (m, 1H).13C NMR (126 MHz, CDCl3): δ 154.82, 152.55, 139.91, 136.95,

135.87, 133.88, 133.25, 130.42, 130.00, 129.74, 129.60, 128.21, 127.94, 125.79, 125.76,

124.99, 124.23, 115.55.IR: 3361, 2922, 1621, 1576, 1502, 1452, 1348, 1175, 799, 690 cm-

1;HRMS-ESI [M+H]+m/z calcd for C23H16F3N2O: 393.1209, found 393.1218.

(E)-2-(2-Chlorostyryl)-3-phenoxyquinoxaline (5e).1HNMR (500

MHz, CDCl3): δ 8.02 (d, J = 16.0 Hz, 1H), 7.94 (dd, J = 8.0, 1.8 Hz,

1H), 7.67 (d, J = 16.0 Hz, 1H), 7.62 – 7.58 (m, 1H), 7.56 (d, J = 8.6 Hz,

2H), 7.51 – 7.48 (m, 2H), 7.40 (t, J = 7.9 Hz, 2H), 7.30 (d, J = 8.5 Hz,

2H), 7.22 (dd, J = 5.9, 4.9 Hz, 2H), 7.18 – 7.16 (m, 1H).13C NMR (126

MHz, CDCl3): δ 154.15, 151.90, 142.55, 138.82, 138.53, 135.08, 133.96, 133.83, 128.59,

128.50, 128.03, 127.88, 127.51, 126.64, 126.30, 124.36, 120.80, 120.44, 28.68.IR: 3361,

2922, 1621, 1576, 1502, 1452, 1348, 1175, 799, 690 cm-1;HRMS-ESI [M+H]+m/z calcd for

C22H16ClN2O: 359.0946, found 359.0951.

(E)-3-(2-Chlorostyryl)-1-phenylquinoxalin-2(1H)-one (6e).1H NMR

(400 MHz, CDCl3): δ 8.12 (d, J = 16.2 Hz, 1H), 7.87 – 7.81 (m, 1H),

7.65 – 7.49 (m, 5H), 7.27 (ddd, J = 8.9, 7.2, 5.3 Hz, 6H), 7.19 (s, 1H),

6.60 (dd, J = 7.6, 2.0 Hz, 1H).13C NMR (126 MHz, MeOD): δ 154.95,

152.42, 136.68, 136.01, 135.07, 134.79, 133.74, 133.23, 130.08,

129.70, 129.35, 129.07, 128.85, 128.76, 128.12, 124.12, 122.03, 115.36.IR: 3361, 2922, 1621,

1576, 1502, 1452, 1348, 1175, 799, 690 cm-1;HRMS-ESI [M+H]+m/z calcd for C22H16ClN2O:

359.0946, found 359.0952.

General procedure for the preparation of 2-phenoxy pyridine derivatives(8a-f) with aryne

To a stirred solution of 4, 6-diphenylpyridin-2(1H)-one (7a-f) (0.24mmol, 1.0 equiv) and


Cesium fluoride (0.72mmol, 3.0 equiv) at room temperature. The mixture was stirred at




concentrated in vacuo. The crude product was purified by column

chromatography (EtoAc in Hexane), resulting the product.

N O

OCH3OCH3H3CO

N

N OCl

N

N OCl

2-Phenoxy-6-phenyl-4-(3,4,5-trimethoxyphenyl)pyridine (8a).1H NMR (400 MHz, CDCl3): δ

7.87 (dd, J = 8.0, 1.4 Hz, 2H), 7.54 (d, J= 1.1 Hz, 1H), 7.36 – 7.27 (m, 5H), 7.17 (dd, J = 8.6, 0.9

Hz, 2H), 7.12 (dd, J = 11.5, 4.2 Hz, 1H), 6.89 (d, J = 1.0 Hz, 1H), 6.75 (s, 2H), 3.84 (s, 6H), 3.82

(s, 3H).13C NMR (126 MHz, CDCl3): δ 163.92, 156.01, 154.38, 153.73, 153.26, 139.05, 138.49,

134.35, 129.54, 129.26, 128.70, 126.92, 124.45, 121.12, 113.54, 107.61, 104.44, 61.04,

56.36. IR: 3345, 2922, 1592, 1649, 1489, 1370, 1306, 1127, 1017, 773, 694 cm-1; HRMS-ESI

[M+H]+m/z calcd for C26H24NO4: 414.17, found 414.1687.

2-(4-Methoxyphenyl)-6-phenoxy-4-(3,4,5-

trimethoxyphenyl)pyridine (8b).1H NMR (400 MHz, CDCl3): δ

7.95 (d, J = 8.9 Hz, 2H), 7.59 (d, J = 1.2 Hz, 1H), 7.45 (dd, J =

8.5, 7.4 Hz, 2H), 7.28 (dd, J = 8.6, 1.0 Hz, 2H), 7.24 (dd, J =

11.5, 4.2 Hz, 1H), 6.95 (dd, J = 9.0, 5.0 Hz, 3H), 6.87 (s, 2H),

3.97 (s, 6H), 3.94 (s, 3H), 3.86 (s, 3H).13C NMR (101 MHz,

CDCl3): δ 163.83, 160.68, 155.73, 154.50, 153.72, 153.15,

139.14, 134.48, 131.13, 129.47, 128.23, 124.32, 121.09, 114.04, 112.63, 106.76, 104.57,

60.98, 56.37, 55.34.IR: 3361, 2922, 1621, 1576, 1502, 1452, 1348, 1175, 799, 690 cm-

1;HRMS-ESI [M+H]+m/z calcd for C27H26NO5: 444.1805, found 444.1799.

4-(3-Nitrophenyl)-2-phenoxy-6-phenylpyridine (8c).1H NMR (400

MHz, CDCl3): δ 8.40 (t, J = 1.9 Hz, 1H), 8.19 (ddd, J = 8.2, 2.2, 1.0

Hz, 1H), 7.86 (ddd, J = 4.6, 2.4, 1.4 Hz, 3H), 7.56 (dd, J = 11.3, 4.6

Hz, 2H), 7.32 (ddd, J = 8.1, 6.2, 4.6 Hz, 5H), 7.19 – 7.11 (m, 3H),

6.91 (d, J = 1.2 Hz, 1H). 13C NMR (126 MHz, CDCl3): δ 164.20,

156.60, 154.08, 150.45, 148.79, 140.18, 137.99, 133.09, 130.21,

129.63, 129.56, 128.77, 126.93, 124.74, 123.82, 122.09, 121.27, 113.10, 107.50. IR: 3398,

2921, 1551, 1489, 1390, 1214, 772, 693 cm-1;HRMS-ESI [M+H]+m/z calcd for C23H17N2O3:

369.1234, found 369.1232.

4-(4-Bromophenyl)-2-(4-chlorophenyl)-6-phenoxypyridine

(8d).1H NMR (400 MHz, CDCl3): δ 7.80 (d, J = 8.7 Hz, 2H), 7.51

(dd, J= 12.8, 4.9 Hz, 3H), 7.44 – 7.39 (m, 2H), 7.37 – 7.31 (m,

2H), 7.29 (d, J = 8.7 Hz, 2H), 7.18 – 7.12 (m, 3H), 6.87 (d, J = 1.2

Hz, 1H).13C NMR (126 MHz, CDCl3): δ 164.18, 154.98, 154.12,

151.97, 137.17, 136.73, 135.40, 132.32, 129.64, 128.89, 128.68,

N O

OCH3OCH3H3CO

H3CO

N O

NO2

N O

Br

Cl

128.16, 124.71, 123.74, 121.24, 112.87, 107.39. IR: 3389, 2921, 1649, 1594, 1488, 1377,

1182, 1011, 763 cm-1;HRMS-ESI [M+H]+m/z calcd for C23H16BrClNO: 436.0098, found

436.0095.

6-Phenoxy-4-phenyl-2,2ꞌ-bipyridine (8e).1H NMR (500 MHz,

CDCl3): δ 8.73 – 8.70 (m, 1H), 8.51 (d, J = 1.3 Hz, 1H), 8.25 (d, J =

8.0 Hz, 1H), 7.81 – 7.75 (m, 3H), 7.55 – 7.46 (m, 5H), 7.31 (dt, J =

15.8, 4.2 Hz, 4H), 7.16 (d, J = 1.3 Hz, 1H).13C NMR (126 MHz,

CDCl3): δ 163.89, 155.46, 154.69, 154.42, 153.27, 149.04, 138.14,

136.96, 129.62, 129.24, 129.02, 127.23, 124.53, 123.89, 121.45, 121.21, 114.18, 108.91.IR:

3345,2921,2851, 1584, 1551, 1490, 1393, 1358, 1214, 949, 763 cm-1;HRMS-ESI [M+H]+m/z

calcd for C22H17N2O: 325.1335, found 325.1337.

4-(Furan-2-yl)-2-phenoxy-6-phenylpyridine (8f).1H NMR (400

MHz, CDCl3): δ 7.89 (dd, J = 8.1, 1.5 Hz, 2H), 7.66 (d, J = 1.1 Hz,

1H), 7.48 – 7.45 (m, 1H), 7.38 – 7.28 (m, 5H), 7.19 – 7.11 (m, 3H),

6.94 (d, J = 1.1 Hz, 1H), 6.81 (dd, J = 3.4, 0.5 Hz, 1H), 6.46 (dd, J =

3.4, 1.8 Hz, 1H).13C NMR (101 MHz, CDCl3): δ 164.13, 156.25,

154.40, 151.49, 143.77, 141.75, 138.36, 129.56, 129.24, 128.64, 126.87, 124.46, 121.12,

112.10, 109.73, 108.95, 103.37.IR: 3398, 2921, 1594, 1559, 1489, 1397, 1215, 1020, 772 cm-

1;HRMS-ESI [M+H]+m/z calcd for C21H16NO2: 314.1176, found 314.118.

1H &13C NMR of 4-Phenoxy-2-phenylquinazoline (3a)

NN

O

N O

O

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)

19-oct-npc-p1Q-BEN

6.98

2.31

1.16

1.00

0.97

2.96

7.20

7.22

7.24

7.25

7.27

7.29

7.30

7.30

7.37

7.39

7.41

7.45

7.47

7.48

7.74

7.75

7.77

7.93

7.95

8.24

8.26

0102030405060708090100110120130140150160170f1 (ppm)

25-oct-c13-maheshQ-BEN 11

5.94

122.

8512

4.39

126.

3512

7.64

128.

9712

9.19

129.

2813

0.25

131.

3813

4.77

138.

51

153.

4915

3.53

160.

71

167.

51

1H &13C NMR of 4-Phenoxy-2-(3,4,5-trimethoxyphenyl)quinazoline (3b)

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)

19-oct-npc-p1Q-TRIMETHOXY

6.75

3.19

1.20

2.09

2.25

1.17

2.04

1.11

1.02

1.00

3.76

3.79

7.20

7.22

7.23

7.27

7.29

7.37

7.39

7.41

7.47

7.49

7.51

7.55

7.76

7.78

7.80

7.80

7.94

7.96

8.24

8.26

0102030405060708090100110120130140150160170f1 (ppm)

25-oct-c13-maheshQ-TRIMETHOXY 55

.91

60.8

8

105.

49

114.

81

122.

4012

3.53

125.

5012

6.74

128.

0512

9.21

132.

9013

3.97

140.

40

152.

7415

2.84

153.

07

159.

11

166.

61

1H &13C NMR of 2-(4-(Methylthio)phenyl)-4-phenoxyquinazoline(3c)

-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)

19-oct-npc-p1Q-P-SCH3

3.37

4.41

5.97

1.08

1.04

1.00

2.08

4.15

7.20

7.22

7.23

7.25

7.27

7.31

7.33

7.34

7.36

7.37

7.39

7.70

7.85

7.87

8.02

8.04

8.40

8.42

2030405060708090100110120130140150160170f1 (ppm)

25-oct-c13-maheshQ-P-SCH3 54

.05

115.

29

123.

4612

6.43

127.

5812

7.92

129.

1612

9.34

129.

8413

2.00

133.

5013

4.81

136.

6213

9.46

151.

81

159.

44

167.

05

1H &13C NMR of 4-Phenoxy-2-(4-(trifluoromethoxy)phenyl)quinazoline (3d)

0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)

19-oct-npc-p1Q-P-OCF3

2.18

3.06

2.07

1.06

1.03

1.00

3.05

7.10

7.12

7.23

7.25

7.37

7.39

7.41

7.45

7.47

7.49

7.75

7.77

7.90

7.92

8.22

8.24

8.26

102030405060708090100110120130140150160170f1 (ppm)

25-oct-c13-maheshQ-P-OCF3 11

5.10

120.

4712

2.03

123.

6212

5.70

127.

0912

8.17

129.

5113

0.10

134.

1013

6.26

151.

0715

2.57

152.

66

158.

56

166.

83

1H &13C NMR of 4-Phenoxy-2-(4-(trifluoromethyl)phenyl)quinazoline (3e)

-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)

19-oct-npc-p1Q-P-CF3

3.19

2.26

3.21

1.08

1.00

1.10

2.07

7.25

7.26

7.27

7.40

7.42

7.44

7.52

7.54

7.56

7.81

7.95

7.97

8.27

8.29

8.33

8.35

0102030405060708090100110120130140150160170f1 (ppm)

25-oct-c13-maheshQ-P-CF3 11

6.16

122.

8312

4.49

126.

5812

8.26

129.

1512

9.52

130.

35

135.

04

141.

82

153.

3615

3.46

159.

26

167.

76

1H &13C NMR of (E)-2-(4-Methoxystyryl)-3-phenoxyquinoxaline(5a)

2.62.83.03.23.43.63.84.04.24.44.64.85.05.25.45.65.86.06.26.46.66.87.07.27.47.67.88.08.28.48.6f1 (ppm)

06-oct-c13-maheshP-OME-1

2.96

2.02

3.39

2.20

2.12

4.09

0.99

1.00

3.77

6.85

6.87

7.17

7.21

7.21

7.23

7.38

7.40

7.47

7.47

7.57

7.59

7.93

7.95

7.95

8.02

8.06

35404550556065707580859095100105110115120125130135140145150155160165170f1 (ppm)

06-oct-c13-maheshP-OME-1 55

.38

114.

30

118.

65

121.

8612

5.28

127.

2812

7.52

128.

3812

9.04

129.

2912

9.37

129.

59

137.

2713

9.30

139.

95

144.

33

153.

1115

5.15

160.

58

1H &13C NMR of (E)-3-(4-Methoxystyryl)-1-phenylquinoxalin-2(1H)-one(6a)

0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)

06-oct-c13-mahesh4-BR-2ER

3.30

1.08

2.09

4.81

6.49

0.96

1.00

3.76

6.56

6.58

6.83

6.85

7.22

7.23

7.25

7.53

7.54

7.55

7.80

7.82

7.82

8.11

8.15

20253035404550556065707580859095105115125135145155165f1 (ppm)

06-oct-c13-maheshP-OME-2 55

.37

114.

3111

5.40

120.

27

124.

0012

8.30

129.

0712

9.32

129.

4012

9.41

129.

5013

0.31

133.

4313

3.64

136.

1313

8.57

153.

3615

4.93

160.

73

1H &13C NMR of (E)-2-Phenoxy-3-(3,4,5-trimethoxystyryl)quinoxaline(5b)

1.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)

15-jun-npc-p1TRImethoxy-1

2.73

5.24

1.88

3.07

2.08

2.19

2.11

0.98

1.00

3.91

3.94

6.94

7.30

7.30

7.32

7.32

7.33

7.50

7.64

7.68

8.01

8.02

8.03

8.04

8.09

8.13

404550556065707580859095100105110115120125130135140145150155160f1 (ppm)

23-june-c13-maheshTRIMETHOXY-1 56

.23

61.0

4

104.

83

120.

3712

2.01

125.

4512

7.30

127.

6512

8.41

129.

3712

9.68

132.

13

137.

7313

9.22

139.

4013

9.87

143.

81

152.

9915

3.46

155.

25

1H &13C NMR of (E)-1-Phenyl-3-(3,4,5-trimethoxystyryl)quinoxalin-2(1H)-one(6b)

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)

15-jun-npc-p1Trimethoxy-2

2.71

5.12

1.00

2.12

4.51

4.39

1.02

1.01

3.89

3.90

6.66

6.67

6.68

6.68

6.90

7.31

7.32

7.33

7.34

7.59

7.63

7.88

7.90

7.91

8.19

8.23

253035404550556065707580859095100105110115120125130135140145150155160f1 (ppm)

24-june-c13-maheshTRIMETHOXY-2 56

.11

61.0

1

104.

88

115.

49

122.

0012

4.16

128.

2312

9.40

129.

4612

9.49

130.

3413

2.14

133.

3713

3.62

135.

9813

9.01

139.

28

152.

8915

3.38

154.

92

1H &13C NMR of 2-((E)-2-(Benzo[d][1,3]dioxol-5-yl)vinyl)-3-phenoxyquinoxaline(5c)

2.42.62.83.03.23.43.63.84.04.24.44.64.85.05.25.45.65.86.06.26.46.66.87.07.27.47.67.88.08.28.4f1 (ppm)

PIP-1PIP-1

1.74

0.93

0.96

1.26

2.95

1.93

1.91

1.25

0.99

0.90

1.00

6.03

6.87

6.89

7.29

7.32

7.33

7.34

7.34

7.34

7.50

7.52

7.58

7.59

7.62

7.66

8.04

8.04

8.06

8.06

8.09

8.13

65707580859095100105110115120125130135140145150155160f1 (ppm)

PIP-1PIP-1 10

1.42

106.

40

108.

58

119.

02

121.

8712

3.73

125.

3312

7.29

127.

5812

8.41

129.

1612

9.62

131.

08

137.

2913

9.35

139.

91

144.

09

148.

3314

8.72

153.

04

155.

14

1H &13C NMR of (E)-3-(2-(Benzo[d][1,3]dioxol-5-yl)vinyl)-1-phenylquinoxalin-2(1H)-one(6c)

2.83.03.23.43.63.84.04.24.44.64.85.05.25.45.65.86.06.26.46.66.87.07.27.47.67.88.08.28.48.68.8f1 (ppm)

PIP-2PIP-2

2.04

1.03

1.04

1.04

1.96

3.29

2.21

2.11

1.01

1.00

6.03

6.67

6.69

6.84

6.86

7.14

7.16

7.23

7.28

7.32

7.33

7.35

7.55

7.59

7.64

7.66

7.91

7.92

7.93

8.17

8.21

3035404550556065707580859095100105110115120125130135140145150155160165f1 (ppm)

PIP-2PIP-2 10

1.40

106.

44

108.

56

115.

42

120.

7012

4.05

124.

0712

8.27

129.

2012

9.36

129.

4613

0.34

131.

1413

3.39

133.

6513

6.07

138.

61

148.

2914

8.87

153.

1715

4.91

1H &13C NMR of (E)-2-Phenoxy-3-(4-(trifluoromethyl)styryl)quinoxaline(5d)

2.22.63.03.43.84.24.65.05.45.86.26.67.07.27.47.67.88.2f1 (ppm)

26-jun-npc-p1PCF3-1

3.29

2.06

2.04

3.00

3.10

0.87

1.00

7.19

7.23

7.25

7.26

7.27

7.41

7.42

7.43

7.45

7.45

7.52

7.52

7.53

7.54

7.55

7.59

7.61

7.62

7.63

7.63

7.64

7.64

7.65

7.73

7.75

7.77

7.81

7.97

7.98

7.98

7.99

7.99

8.00

8.08

8.12

35404550556065707580859095100105110115120125130135140145150155160f1 (ppm)

14-july-c13-maheshPCF3-1 12

1.87

123.

3812

5.49

125.

7712

5.80

127.

3712

7.79

127.

8312

8.66

129.

6812

9.84

135.

70

139.

7413

9.83

139.

8814

3.17

152.

88

155.

26

1H &13C NMR of (E)-1-Phenyl-3-(4-(trifluoromethyl)styryl)quinoxalin-2(1H)-one(6d)

2.22.63.03.43.84.24.65.05.45.86.26.67.07.27.47.67.88.28.6f1 (ppm)

30-june-c13-maheshPCF3-2

1.02

4.99

1.32

4.55

3.23

1.13

1.00

6.59

6.59

6.59

6.60

6.60

6.61

7.23

7.25

7.25

7.26

7.27

7.55

7.56

7.57

7.58

7.65

7.67

7.67

7.71

8.15

8.18

707580859095100105110115120125130135140145150155f1 (ppm)

30-june-c13-maheshPCF3-2 11

5.55

124.

2312

4.99

125.

7612

5.79

127.

9412

8.21

129.

6012

9.74

130.

0013

0.42

133.

2513

3.88

135.

8713

6.95

139.

91

152.

55

154.

82

1H &13C NMR of (E)-2-(2-Chlorostyryl)-3-phenoxyquinoxaline(5e)

4.24.44.64.85.05.25.45.65.86.06.26.46.66.87.07.27.47.67.88.08.28.4f1 (ppm)

11-june-c13-maheshC1-1

0.76

2.44

1.99

1.90

2.04

1.92

0.99

0.94

0.88

1.00

7.17

7.17

7.20

7.22

7.22

7.22

7.29

7.31

7.39

7.40

7.42

7.48

7.48

7.49

7.50

7.50

7.51

7.51

7.55

7.57

7.59

7.60

7.61

7.65

7.69

7.94

7.94

7.95

7.96

8.00

8.04

859095100105110115120125130135140145150155160f1 (ppm)

11-june-c13-maheshC1-1 12

0.44

120.

80

124.

3612

6.30

126.

6412

7.51

127.

8812

8.03

128.

5012

8.59

133.

8313

3.96

135.

08

138.

5313

8.82

142.

55

151.

90

154.

15

1H &13C NMR of (E)-3-(2-Chlorostyryl)-1-phenylquinoxalin-2(1H)-one(6e)

2.42.62.83.03.23.43.63.84.04.24.44.64.85.05.25.45.65.86.06.26.46.66.87.07.27.47.67.88.08.28.48.6f1 (ppm)

02-sep-npc-p1CL-2

0.93

1.33

6.02

5.45

1.04

0.99

6.59

6.59

6.61

6.61

7.19

7.24

7.25

7.25

7.26

7.26

7.28

7.30

7.51

7.53

7.57

7.59

7.83

7.85

7.85

8.10

8.14

80859095100105110115120125130135140145150155160165170f1 (ppm)

15-june-c13-maheshC1-2 11

5.36

122.

03

124.

1212

8.12

128.

7612

8.85

129.

0712

9.35

130.

08

133.

2313

3.74

134.

7913

5.07

136.

0113

6.68

152.

42

154.

95

1H &13C NMR of 2-Phenoxy-6-phenyl-4-(3,4,5-trimethoxyphenyl)pyridine (8a)

1.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)

05-aug-npc-p1TRI-PY

3.05

5.33

1.92

0.91

1.15

1.88

4.87

1.00

1.96

3.82

3.84

6.75

6.89

6.89

7.16

7.18

7.18

7.31

7.33

7.54

7.54

7.85

7.86

7.87

7.88

102030405060708090100110120130140150160170f1 (ppm)

05-oct-c13-maheshTRI-PY 56

.36

61.0

4

104.

44

107.

61

113.

54

121.

1212

4.45

126.

9212

8.70

129.

2612

9.54

134.

35

138.

4913

9.05

153.

2615

3.73

154.

3815

6.01

163.

92

1H &13C NMR of 2-(4-Methoxyphenyl)-6-phenoxy-4-(3,4,5-trimethoxyphenyl)pyridine(8b)

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)

08-july-c13-maheshPY

2.98

3.08

5.80

2.07

3.06

1.13

2.06

2.09

1.00

1.99

3.86

3.94

3.97

6.87

6.94

6.94

6.95

6.98

7.28

7.29

7.30

7.45

7.45

7.59

7.59

7.94

7.96

0102030405060708090100110120130140150160170f1 (ppm)

08-july-c13-maheshPY 55

.34

56.3

7

60.9

8

104.

5710

6.76

112.

6311

4.04

121.

0912

4.32

128.

2312

9.47

131.

1313

4.48

139.

14

153.

1515

3.72

154.

5015

5.73

160.

68

163.

83

1H &13C NMR of 4-(3-Nitrophenyl)-2-phenoxy-6-phenylpyridine(8c)

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)

13-july-npc-p1PY-NO2-2

0.90

3.11

5.13

2.10

3.08

1.00

0.93

6.91

6.92

7.15

7.17

7.30

7.32

7.57

7.58

7.85

7.85

8.17

8.18

8.18

8.20

8.20

8.40

8.40

8.41

102030405060708090100110120130140150160170f1 (ppm)

22-july-c13-maheshPY-NO2-2 10

7.50

113.

10

121.

2712

2.09

123.

8212

4.74

126.

9312

8.77

129.

5612

9.63

130.

2113

3.09

137.

9914

0.18

148.

7915

0.45

154.

0815

6.60

164.

20

1H &13C NMR of 4-(4-Bromophenyl)-2-(4-chlorophenyl)-6-phenoxypyridine (8d)

0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)

10-aug-npc-p1PY-BRCL

1.00

3.39

2.30

2.50

2.32

3.44

2.16

6.87

6.87

7.16

7.27

7.30

7.43

7.49

7.50

7.52

7.79

7.81

253035404550556065707580859095100105110115120125130135140145150155160165170f1 (ppm)

05-oct-c13-maheshPY-Br-CL 10

7.39

112.

87

121.

2412

3.74

124.

7112

8.16

128.

6812

8.89

129.

6413

2.32

135.

4013

6.73

137.

17

151.

9715

4.12

154.

98

164.

18

1H &13C NMR of 6-Phenoxy-4-phenyl-2,2ꞌ-bipyridine(8e)

0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)

11-aug-c13-maheshPY-PY-2

1.02

4.14

5.12

3.04

0.99

0.98

1.00

7.16

7.16

7.27

7.29

7.30

7.32

7.33

7.33

7.48

7.48

7.48

7.49

7.49

7.50

7.51

7.51

7.52

7.53

7.54

7.75

7.76

7.77

7.77

7.78

7.78

7.79

7.79

7.80

8.24

8.26

8.51

8.51

8.71

8.71

8.71

8.72

8.72

8.72

3035404550556065707580859095100105110115120125130135140145150155160165170175f1 (ppm)

11-aug-c13-maheshPY-PY-2 10

8.91

114.

18

121.

2112

1.45

123.

8912

4.53

127.

2312

9.02

129.

2412

9.62

136.

9613

8.14

149.

04

153.

2715

4.42

154.

6915

5.46

163.

89

1H &13C NMR of 4-(Furan-2-yl)-2-phenoxy-6-phenylpyridine(8f)

1.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)

pyPP-FF-2

0.95

1.00

0.99

4.17

6.36

0.96

1.07

2.09

6.45

6.45

6.46

6.46

6.94

6.94

7.15

7.15

7.17

7.18

7.32

7.33

7.34

7.66

7.66

7.88

7.88

7.90

7.90

30405060708090100110120130140150160170f1 (ppm)

05-oct-c13-MaheshPY-FF-2 10

3.37

108.

9510

9.73

112.

10

121.

1212

4.46

126.

8712

8.64

129.

2412

9.56

138.

3614

1.75

143.

77

151.

4915

4.40

156.

25

164.

13

X-ray crystallographic data ofcompound 8c:

X-ray intensity data of 7234 reflections (of which 3530 unique) were collected on X’calibur

CCD area-detector diffractometer equipped with graphite monochromated MoKradiation

( = 0.71073 Å). The crystal used for data collection was of dimensions 0.30 x 0.20 x 0.20

mm. The cell dimensions were determined by least-squares fit of angular settings of 1788

reflections in the range 3.93 to 27.57o. The intensities were measured by scan mode for

ranges 3.53 to 26.00o. 2176 reflections were treated as observed (I > 2(I)). Data were

corrected for Lorentz, polarisation and absorption factors. The structure was solved by direct

methods using SHELXS97 [1]. All non-hydrogen atoms of the molecule were located in the

best E-map. Full-matrix least-squares refinement was carried out using SHELXL97 [1]. The

final refinement cycles converged to an R = 0.0445 and wR (F2) = 0.0911 for the observed

data. Residual electron densities ranged from -0.126 <<0.158 eÅ-3. Atomic scattering

factors were taken from International Tables for X-ray Crystallography (1992, Vol. C, Tables

4.2.6.8 and 6.1.1.4). The crystallographic data are summarized in Table 1. An ORTEP view of

the compound with atomic labelling is shown in Fig.1 [2]. The geometry of the molecule was

calculated using the WinGX [3], PARST [4] and PLATON [5] software’s. The compound 4-(3-

Nitrophenyl)-2-phenoxy-6-phenylpyridine C23H17N2O3(8c), crystallizes in the monoclinic space

group C2/c with the unit-cell parameters: a,b,c as 22.076 (2), 10.1079 (8), 16.921 (2)Å,β =

107.250 (11)o and Z = 8. The crystal structure was solved by direct methods using single-

crystal X-ray diffraction data collected at room temperature and refined by full-matrix least-

squares procedures to a final R-value of 0.0445 for 2176 observed reflections.

Fig. 1: ORTEP of (CCDC No. 1451640) compound 8c whichcrystallized in monoclinic space

group C2/cUnit Cell Parameters: a = 22.076 (2)Å,b = 10.1079 (8)Å, c = 16.921(2) Åfor 8c.

N O

NO2

Table S1: Crystal and diffraction parameters of 8c

Chemical formula C23H16N2O3

Mr 368.38Crystal system, space group MONOCLINIC, C2/cTemperature (K) 293a, b, c (Å) 22.076 (2), 10.1079 (8), 16.921 (2)β (°) 107.250 (11)V (Å3) 3605.9 (6)Z 8F(000) 1536Dx (Mg m−3) 1.357Radiation type Mo KαNo. of reflections for cell measurement 1788θ range (°) for cell measurement 3.9–27.6µ (mm−1) 0.09Crystal shape BLOCKColour WhiteCrystal size (mm) 0.30 × 0.20 × 0.20Scan method ω scansAbsorption correction Multi-scanTmin, Tmax 0.893, 1.000No. of measured, independent andobserved [I> 2σ(I)] reflections 7234, 3530, 2176

Rint 0.028θ values (°) θmax = 26.0, θmin = 3.5(sin θ/λ)max (Å−1) 0.617Range of h, k, l h = −27→17, k = −12→8, l = −20→20Refinement on F2

R[F2> 2σ(F2)], wR(F2), S 0.0445, 0.1090, 0.993No. of reflections 3530No. of parameters 254No. of restraints 0H-atom treatment H-atom parameters constrained

Weighting scheme w = 1/[σ2(Fo2) + (0.0433P)2]

where P = (Fo2 + 2Fc

2)/3(Δ/σ)max < 0.001Δρmax, Δρmin (e Å−3) 0.16, −0.13

X-ray crystallographic data ofcompound 8e:

X-ray intensity data of 5807 reflections (of which 3223 unique) were collected on X’calibur

CCD area-detector diffractometer equipped with graphite monochromated MoKradiation

( = 0.71073 Å). The crystal used for data collection was of dimensions 0.30 x 0.20 x 0.20

mm. The cell dimensions were determined by least-squares fit of angular settings of 1471

reflections in the range 4.12 to 26.09o. The intensities were measured by scan mode for

ranges 3.52 to 26.00o. 1919 reflections were treated as observed (I > 2(I)). Data were

corrected for Lorentz, polarisation and absorption factors. The structure was solved by direct

methods using SHELXS97. 23 All non-hydrogen atoms of the molecule were located in the

best E-map. Full-matrix least-squares refinement was carried out using SHELXL97. 23The final

refinement cycles converged to an R = 0.0533 and wR (F2) = 0.1235 for the observed data.

Residual electron densities ranged from -0.162 <<0.172 eÅ-3. Atomic scattering factors

were taken from International Tables for X-ray Crystallography (1992, Vol. C, Tables 4.2.6.8

and 6.1.1.4). The crystallographic data are summarized in Table 2.Compound 6-phenoxy-4-

phenyl-2, 2ꞌ-bipyridine C22H16N2O (8e), crystallizes in the triclinic space group P-1 with the

unit-cell parameters: a,b,c,α, β, γ as 8.1694 (12), 9.7524 (16), 11.8980 (18)Å,73.012

(14), 75.211 (13), 67.352 (15)o and Z = 2. The crystal structures 8e was solved by direct

methods using single-crystal X-ray diffraction data collected at room temperature and

refined by full-matrix least-squares procedures to final R-values of 0.0579 for 1636 observed

reflections and 0.0533 for 1919 observed reflections respectively.

Crystal structure of 6-phenoxy-4-phenyl-2, 2ꞌ-bipyridine (8e)

NN O

8e, 60% crystal stucture 8e

Fig. 2: ORTEP of (CCDC No. 1451639) compound 8ewhichcrystallized in triclinic space group

P-1Unit Cell Parameters: a = 8.1694 (12) Å, b = 9.7524 (16) Å, c = 11.8980 (18) Å.

Table S2: Crystal and diffraction parameters of 8e.

Chemical formula C22H16N2OMr 324.37Crystal system, space group TRICLINIC, P1Temperature (K) 293a, b, c (Å) 8.1694 (12), 9.7524 (16), 11.8980 (18)α, β, γ (°) 73.012 (14), 75.211 (13), 67.352 (15)V (Å3) 825.6 (2)Z 2F(000) 340Dx (Mg m−3) 1.305Radiation type Mo KαNo. of reflections for cell measurement 1471θ range (°) for cell measurement 4.1–26.1µ (mm−1) 0.08Crystal shape BLOCKColour WhiteCrystal size (mm) 0.30 × 0.20 × 0.20Diffractometer Xcalibur, Sapphire3 diffractometerScan method ω Scan scansAbsorption correction Multi-scan Tmin, Tmax 0.868, 1.000No. of measured, independent andobserved [I > 2σ(I)] reflections

5807, 3223, 1919

Rint 0.028θ values (°) θmax = 26.0, θmin = 3.5(sin θ/λ)max (Å−1) 0.617Range of h, k, l h = −10→10, k = −12→5, l = −14→14Refinement on F2

R[F2 > 2σ(F2)], wR(F2), S 0.0533, 0.1519, 1.042No. of reflections 3223No. of parameters 227No. of restraints 0H-atom treatment H-atom parameters constrainedWeighting scheme w = 1/[σ2(Fo

2) + (0.058P)2 + 0.0032P] where P = (Fo

2 + 2Fc2)/3

(Δ/σ)max < 0.001Δρmax, Δρmin (e Å−3) 0.17, −0.16

References

1. Sheldrick GM (2008) Acta Cryst A64: 112

2. Farrugia LJ (1997) J Appl Cryst30:565

3. Farrugia LJ (1999) J Appl Cryst32:837

4. Nardelli M (1995) J Appl Cryst 28:659

5. Spek AL (2009) Acta Cryst D65: 148–155

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