The chemistry of heterocycles: structure, reactions, syntheses, and applications

Theophil Eicher, Siegfried Hauptmann9783527307203, 3-527-30720-6

The second edition of this “classic” among textbooks on heterocycle chemistry. Here, Theophil Eicher and Siegfried Hauptmann, both renowned authors of many successful such works, present all the important aspects of this fascinating field in a clear manner. – completely revised – enlarged – numerous Q&As help readers to deepen their knowledge – covers the very latest topics, such as metal-catalyzed coupling reactions – systematic substance nomenclature – comprehensive overview of all the important substance classes. A must-have for advanced students of organic chemistry as well as for chemists looking for a quick overview of the field.

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Table of contents :
Cover Page……Page 1
Further Reading from Wiley-VCH……Page 3
Title Page……Page 4
© 2003 WILEY-VCH GmbH & Co. KGaA, Weinheim……Page 5
Foreword……Page 7
Preface……Page 8
Contents……Page 9
Abbreviations and Symbols……Page 13
1 The Structure of Heterocyclic Compounds……Page 15
2 Systematic Nomenclature of Heterocyclic Com-pounds……Page 19
2.1 Hantzsch-Widman Nomenclature……Page 20
2.2 Replacement Nomenclature……Page 25
2.3 Examples of Systematic Nomenclature……Page 26
2.4 Important Heterocyclic Systems……Page 30
3.1 Oxirane……Page 31
3.2 Thiirane……Page 38
3.3 2H-Azirine……Page 40
3.4 Aziridine……Page 42
3.6 Oxaziridine……Page 46
3.7 3H-Diazirine……Page 48
3.8 Diaziridine……Page 49
References……Page 51
4.1 Oxetane……Page 52
4.2 Thietane……Page 55
4.3 Azete……Page 56
4.4 Azetidine……Page 57
4.5 1,2-Dioxetane……Page 59
4.7 l,2-Dihydro-l,2-diazete……Page 62
4.8 1,2-Diazetidine……Page 63
References……Page 65
5.1 Furan……Page 66
5.2 Benzo[£]furan……Page 77
5.3 Isobenzofuran……Page 79
5.4 Dibenzofuran……Page 80
5.5 Tetrahydrofuran……Page 81
5.6 Thiophene……Page 85
5.7 Benzo[A]thiophene……Page 94
5.8 Benzo[c] thiophene……Page 96
5.9 2,5-Dihydrothiophene……Page 97
5.10 Thiolane……Page 98
5.11 Selenophene……Page 99
5.12 Pyrrole……Page 100
5.13 Indole……Page 113
5.14 Isoindole……Page 124
5.15 Carbazole A,B The numbering of carbazole (benzo[6]indole) predates the introduction of systematic no-menclature……Page 125
5.16 Pyrrolidine……Page 128
5.17 Phosphole……Page 130
5.18 1,3-Dioxolane……Page 132
5.19 1,2-Dithiole……Page 133
5.20 1,2-Dithiolane……Page 134
5.21 1,3-Dithiole……Page 135
5.23 Oxazole……Page 136
5.24 Benzoxazole……Page 146
5.25 4,5-Dihydrooxazole……Page 148
5.26 Isoxazole……Page 152
5.27 4,5-Dihydroisoxazole……Page 158
5.28 2,3-Dihydroisoxazole……Page 161
5.29 Thiazole……Page 163
5.30 Benzothiazole……Page 169
5.31 Penam……Page 173
5.32 Isothiazole……Page 174
5.33 Imidazole……Page 179
5.34 Benzimidazole……Page 188
5.35 Imidazolidine……Page 192
5.36 Pyrazole……Page 193
5.37 Indazole……Page 199
5.38 4,5-Dihydropyrazole……Page 200
5.39 Pyrazolidine……Page 203
5.40 1,2,3-Oxadiazole……Page 205
5.41 1,2,5-Oxadiazole……Page 207
5.42 1,2,3-Thiadiazole……Page 210
5.43 1,2,4-Thiadiazole……Page 212
5.44 1,2,3-Triazole……Page 214
5.45 Benzotriazole……Page 219
5.46 1,2,4-TriazoIe……Page 222
5.47 Tetrazole……Page 226
References……Page 232
6.1 Pyrylium ion……Page 236
6.2 2H-Pyran……Page 245
6.3 2H-Pyran-2-one……Page 247
6.4 3,4-Dihydro-2H-pyran……Page 253
6.5 Tetrahydropyran……Page 257
6.6 2H-Chromene……Page 259
6.7 2H-Chromen-2-one……Page 261
6.8 1-Benzopyrylium ion……Page 266
6.9 4H-Pyran……Page 269
6.10 4H-Pyran-4-one……Page 271
6.11 4H-Chromene……Page 274
6.12 4//-Chromen-4-one……Page 275
6.13 Chroman……Page 280
6.14 Pyridine……Page 283
6.15 Pyridones……Page 0
6.15 Pyridones……Page 324
6.16 Quinoline……Page 330
6.17 Isoquinoline……Page 350
6.18 Quinolizinium Ion……Page 363
6.19 Dibenzopyridines……Page 367
6.20 Piperidine……Page 374
6.21 Phosphabenzene……Page 379
6.22 1,4-Dioxin, 1,4-Dithiin, 1,4-Oxathiin……Page 383
6.23 1,4-Dioxane……Page 385
6.24 Oxazines……Page 388
6.25 Morpholine……Page 395
6.26 1,3-Dioxane……Page 397
6.27 1,3-Dithiane……Page 402
6.28 Cepham……Page 403
6.29 Pyridazine……Page 407
6.30 Pyrimidine……Page 412
6.31 Purine……Page 422
6.32 Pyrazine……Page 431
6.33 Piperazine……Page 436
6.34 Pteridine……Page 439
6.35 Benzodiazines……Page 444
6.36 1,2,3-Triazine……Page 451
6.37 1,2,4-Triazine……Page 454
6.38 1,3,5-Triazine……Page 460
6.39 1,2,4,5-Tetrazine……Page 465
References……Page 471
7.1 Oxepin……Page 475
7.2 Thiepin……Page 479
7.3 Azepine……Page 480
7.4 Diazepines……Page 486
References……Page 492
8.1 Azocine……Page 494
8.2 Heteronines and larger-membered heterocycles……Page 496
8.3 Tetrapyrroles……Page 499
References……Page 508
9 Problems and Their Solutions……Page 510
10.1 General Subject Index……Page 559
10.2 Index of Named Reactions……Page 568
Back Cover……Page 571