RODD'S CHEMISTRY OF CARBON COMPOUNDSSupplements to the 2nd Edition (Editor S. Coffey) of RODD'S...
Transcript of RODD'S CHEMISTRY OF CARBON COMPOUNDSSupplements to the 2nd Edition (Editor S. Coffey) of RODD'S...
Supplements to the 2nd Edition (Editor S . Coffey) of
RODD'S CHEMISTRY O F
CARBON COMPOUND S
A modern comprehensive treatise
Edited byMARTIN F. ANSELL
Ph.D., D .Sc .(London) F.R .S .C . C . Chem .Reader Emeritus, Department of Chemistry,
Queen Mary College, University ofLondon, Great Britai n
Supplement to
VOLUME IV HETEROCYCLIC COMPOUND S
PART C :
Five-Membered Heterocyclic Compounds wit hTwo Hetero-Atoms in the Ring from Groups V and/or V I
of the Periodic Tabl e
PART D :
Five-Membered Heterocyclic Compounds with More thanTwo Hetero-Atoms in the Ring
VOLUME IV C and D
Heterocyclic Compounds : Five-membered Heterocyclic Compounds with Two Hetero -atoms in the Ring from Groups V and/or VI of the Periodic Tabl e
Five-membered Heterocyclic Compounds with More than Two Hetero-atoms in the Rin g
List of contributors viPreface vi iOfficial publications ; scientific journals and periodicalsList of common abbreviations and symbols used
Chapter 16. Five-membered Heterocyclic Compounds wit hTwo Nitrogen Atoms in the Ring
by S .T . MULLIN S
1 . Pyrazole 1(a) Preparation 1(b) Cyclisation 1(c) From other heterocycles 1 1(d) Pyrazole derivatives
1 1(i) N-oxides, 11 - (ii) N-alkyl and N-aryl derivatives, 11 - (iii) N-acylderivatives, 13 - (iv) C-alkyl and C-aryl derivatives, 1 6
(e) Fused systems 1 8(f) Reduced systems 2 1
2 . Indazoles 25(a) Preparation 25(b) From benzoid precursors 25(c) Miscellaneous 32(d) Indazole derivatives
33(i) Alkyl and aryl derivatives, 33 - (ii) Carboxylic acid derivativesand indazolediones, 34 - (iii) Aminoindazoles, 36 - (iv) Halogenatedindazoles, 36 -
(e) Fused systems
3 7(i) Pyrazoloindazoles, 37 - (ii) Triazoloindazoles, 39 - (iii) Benzinda-zoles, 41 -
(f) Reduced indazoles 4 13 . Imidazoles 43
(a) Preparation 43(b) Cyclisation 44(c) Other cyclisation reactions 49(d) From other heterocycles 52
(e) Imidazole derivatives
5 3(i) N-substituted derivatives, 53 - (ii) C-alkyl- and C-arylimidazoles ,55 - (iii) Halogenated derivatives, 58 - (iv) Nitrogen derivatives, 62 - (v )Sulphur derivatives, 64 - (iv) Metalloimidazoles, 64 -
(1) Miscellaneous 6 6(g) Fused imidazoles 6 8(h) Reduced imidazoles 7 6
4 . Benzimidazoles 7 9(a) Synthesis 7 9(b) Benzimidazole derivatives 8 3
(i) N-oxides, 83 - (ii) N-alkyl derivatives, 84 - (iii) C-alkyl derivatives,85 - (iv) Amino derivatives, 87 - (v) Sulphur containing derivatives ,90 - (vi) Aldehydes and ketones, 91 -
(c) Fused benzimidazole derivatives 9 2
Chapter 17. Five-membered Heterocyclic Compounds withTwo Different Hetero-atoms in the Ring
by J .D . HEPWORTH and M. WAINWRIGH T
1 . Isoxazole and its derivatives 95(a) Isoxazoles
96(i) Synthesis, 96 - (ii) Reactions, 10 7
(b) Reduced Systems
11 5(i) Synthesis of isoxazolines, 115 - (ii) Synthesis of isoxazolidines, 123 -(iii) Reactions of isoxazolines and isoxazolidines, 127 -
2 . Benzisoxazoles 129(a) 1,2-Benzisoxazoles (Indoxazenes)
130(i) Synthesis, 130 - (ii) Properties and reactions, 131 -
(b) 2,1-Benzisoxazoles (Anthranils)
13 3(i) Synthesis, 133 - (ii) Reactions, 137 -
3 . Oxazole and its derivatives 14 1(a) Oxazoles
142(i) Synthesis, 142 - (ii) Reactions, 151 -
(b) Reduced systems 162Benzoxazoles 174(a) Synthesis 174(b) Reactions 18 1
5 . Isothiazole and its derivatives 18 4(a) Isothiazoles
18 4(i) Synthesis, 184 - (ii) Reactions, 188 -
6. Benzisothiazoles 19 2(a) Synthesis 19 2(b) Synthesis of benzisothiazole-1,1-dioxides 19 4(c) Reactions 196(d) Reactions of saccharin 200
7. Thiazole and its derivatives 205(a) Thiazoles
205(i) Synthesis, 205 - (ii) Reactions, 215 -
(b) Thiazolinethiones 222
(c) Thiazolidines 22 5(d) Reactions of the thiazole system yielding fused heterocycles
22 7(i) Oxygen- and sulphur-containing fused thiazoloheterocycles, 227 -
(e) Nitrogen-containing fused thiazoloheterocycles 229(i) 5-Membered fused rings containing one nitrogen atom, 229 -(ii) 5-Membered fused rings containing two nitrogen atoms, 230 -(iii) 5-Membered fused rings containing three nitrogen atoms, 232 -(iv) 6-Membered fused rings containing one nitrogen atom, 233 -(v) 6-Membered fused rings containing two nitrogen atoms, 234 -(vi) 6-Membered fused rings containing three nitrogen atoms, 235 -(vii) Larger nitrogen-containing fused rings, 236 -
8 . Benzothiazoles 23 7(a) Synthesis 23 7(b) Reactions 24 1
9 . Isoselenazoles 24810 . Benzisoselenazoles 249
(a) Synthesis 249(b) Reactions 25 0
11 . Isotellurazoles and benzisotellurazoles 25 212 . Selenazoles 25 3
(a) Synthesis 25 3(b) Reactions 25 4(c) Fused heterocyclic selenazoles 25 5
13 . Benzoselenazoles 25 614 . Benzotellurazoles 25 7
Chapter 18. Five-membered Heterocyclic Compounds wit hThree Hetero-atoms in the Ring
by D.J . ROWE
1 . Introduction 2592 . 1,2,3-Triazoles 259
(a) Synthesis of 1,2,3-triazoles
259(i) 1,3-Dipolar addition reactions, 259 -
(b) Oxidative synthesis 264(c) Reactions and uses of 1,2,3-triazoles 265(d) Extrusion of nitrogen from benzotriazoles 269
3 . Triazolines 278(a) Synthesis of triazolines
279(i) 1,3-Dipolar addition of azides to alkenes, 279 -
4. 1,2,4-Triazoles 285(a) Synthesis
285(i) By cycloaddition, 296 -
(b) Reactions 2975 . 1,2,3-Oxadiazoles 2986 . 1,2,4-Oxadiazoles 299
(a) Synthesis 29 9(b) 1,3-Dipolar cycloaddition methods 29 9(c) Other methods 306
(d) Reactions 30 77 . 1,3,4-Oxadiazoles 30 9
(a) Synthesis 30 9(b) From acyl hydrazides 30 9(c) Oxidative methods 31 1(d) Other methods 31 3(e) Reactions of 1,3,4-oxadiazoles 31 3
8 . 1,2,5-Oxadiazoles 31 5(a) Synthesis 31 5(b) Reactions 31 7
9 . 1,2,3-Thiadiazoles 31 8(a) Synthesis and reactions 31 9
10 . 1,2,4-Thiadiazoles 32 3(a) Synthesis 32 3(b) Oxidative cyclisation 323(c) Cycloaddition of nitrite sulphides 325
11 . 1,2,5-Thiadiazoles 327(a) Synthesis 32 7(b) Reactions 330
12 . 1,3,4-Thiadiazoles 33 1(a) Synthesis
33 1(i) Oxidative cyclisation, 331 - (ii) Non-oxidative methods, 334 - (iii )Cycloaddition methods, 339 -
13 . Selenadiazoles 34 1(a) Synthesis and reactions 342
14 . Other five-membered rings with three heteroatoms 346(a) Oxathiazoles 346(b) 1,2,4-Dithiazoles 34 7(c) 1,4,2-Dithiazoles 34 7
15 . Heterocyclic rearrangements 348(a) The Dimroth rearrangement
348(i) The mechanism of the Dimroth rearrangement, 350 -- (ii) Th eDimroth rearrangement in other heterocycles, 355 -
(b) The Boulton-Katritzky scheme 360(c) Photochemical rearrangements 370
Chapter 19. Five-membered Heterocyclic Compound.: withFour Hetero-atoms in the Ring
by J .H. LITTLE
Introduction 37 51 . Tetrazoles 37 5
(a) Synthesis 37 6(b) Spectroscopic and other studies 382(c) Thermolysis and photolysis 38 5(d) Other reactions 388
(e) Applications
394(i) Pharmaceuticals, 394 - (ii) Herbicides, 395 - (iii) Polymers, 395 -(iv) Oligonucleotide synthesis, 396 -
2. Oxatriazoles 39 63. Thiatriazoles 39 9
(a) 1,2,3,4-Thiatriazoles
39 9(i) Synthesis, 399 -
(b) 1,2,3,5-Thiatriazoles 40 44. Dioxathiazoles and oxathiadiazoles 40 65. Dithiadiazoles and dioxadiazoles 40 8
(a) 1,2,3,5-dithiadiazoles 40 8(b) 1,3,2,4-Dithiadiazoles 41 1(c) Dioxadiazoles 41 4
6. Phosphorus-containing heterocycles 41 4(a) Triazaphospholes
41 4(i) 1,2,3,4-Triazaphospholes, 414 - (ii) 1,2,4,3-Triazaphospholes, 417 -
(b) Diazadiphospholanes 42 0(c) Oxadiazaphospholes 42 1(d) Thiadiazaphospholes 42 2(e) Tetraphospholanes 42 3
Index 427