This classical textbook in the best sense of the word is now completely revised, updated and with more than 40% new content. The approved ordering system according to the ring size of the heterocycles has been retained, while the important chapter on 'Problems and their Solutions' has been almost completely renewed by introduction of up-to-date scientific exercises, resulting in a great tool for self-testing and exams. There was maintained a chapter on nomenclature and a helpful index of name reactions. With approximately 1,000 new literature citations, this book remains a brilliant gateway to modern heterocyclic science for master and graduate students, as well as PhDs and researchers entering the field. 'If you want quick information about the basic (or acidic!) properties of a heterocycle, some interesting facts, or an assorted few ways of making it, this book provides a welcoming, accurate, and concise introduction.' Angewandte Chemie IE 'Eicher and Hauptmann provide an up to date introduction to the field for the advanced undergraduate and graduate students. ... The book is carefully produced to a very high standard.' European Journal of Medicinal Chemistry

Theophil Eicher studied chemistry at the University of Heidelberg and obtaind his Ph.D. under Georg Wittig in 1960. After postdoctoral work at Columbia University, New York, in the laboratories of Ronald Breslow, he habilitated 1967 at the University of Wurzburg under Siegfried Hunig. In 1974 he was appointed as Associate Professor at the University of Hamburg, in 1976 as Full Professor of Organic Chemistry at the University of Dortmund. Since 1982, he worked as Full Professor at the University of the Saarland, Saarbrucken, and was retired in 2000. Professor Eichers research interests concerned the synthetic chemistry of cyclopropenones and triafulvenes, as well as natural product synthesis in the field of bryophyte constituents. He is co-author of several books. Jointly with L. F. Tietze, he was awarded the literature prize of the "Fonds der chemischen Industrie". He is Dr. h. c. and Prof. a. h. of the Facultad de Quimica of the Universidad de la Republica, Montevideo/Uruguay. Siegfried Hauptmann studied chemistry at the University of Leipzig. In 1958, he obtained his Ph.D. under Wilhelm Treibs, habilitated in the field of organic chemistry in 1961 and became Assistant Professor and later Full Professor at the University of Leipzig. He was retired in 1996. His research interests were centred predominantly to the field of synthetic organic chemistry and reaction mechanisms. Professor Hauptmann was author and co-author of several books and deceased in April, 2011. Andreas Speicher studied chemistry at Saarland University, Saarbrucken. He obtained his Ph.D. in 1994 under Theophil Eicher and was honoured with the Eduard-Martin-Award of his University. He started his independent scientific career and completed habilitation in 2003 (Privatdozent). He is head of a research group and university lecturer for organic chemistry at the Saarland University and was appointed extraordinary professor in 2011. He is temporary holding a guest professorship at the University of Strasbourg/France since 2006 and is co-author of several books. His research interests are directed to synthesis and characterization of chemically and biologically relevant natural products, especially to axially chiral macrocyclic compounds.

Preface to the Third Edition ix

Abbreviations and Symbols xi

1 The Structure of Heterocyclic Compounds 1

Reference 4

2 Systematic Nomenclature of Heterocyclic Compounds 5

2.1 Hantzsch-Widman Nomenclature 6

2.2 Replacement Nomenclature 11

2.3 Examples of Systematic Nomenclature 12

2.4 Important Heterocyclic Systems 15

3 Three-Membered Heterocycles 17

3.1 Oxirane 17

3.2 Thiirane 26

3.3 2H-Azirine 29

3.4 Aziridine 32

3.5 Dioxirane 37

3.6 Oxaziridine 38

3.7 3H-Diazirine 40

3.8 Diaziridine 40

References 41

4 Four-Membered Heterocyles 45

4.1 Oxetane 45

4.2 Thietane 49

4.3 Azete 50

4.4 Azetidine 51

4.5 1,2-Dioxetane 55

4.6 1,2-Dithiete 57

4.7 1,2-Dihydro-1,2-diazete 58

4.8 1,2-Diazetidine 58

References 59

5 Five-Membered Heterocycles 61

5.1 Furan 61

5.2 Benzo[b]furan 80

5.3 Isobenzofuran 84

5.4 Dibenzofuran 86

5.5 Tetrahydrofuran 87

5.6 Thiophene 90

5.7 Benzo[b]thiophene 101

5.8 Benzo[c]thiophene 104

5.9 2,5-Dihydrothiophene 105

5.10 Thiolane 106

5.11 Selenophene 107

5.12 Pyrrole 108

5.13 Indole 125

5.14 Carbazole 148

5.15 Isoindole 150

5.16 Indolizine 152

5.17 Pyrrolidine 157

5.18 Phosphole 161

5.19 1,3-Dioxolane 162

5.20 1,2-Dithiole 163

5.21 1,2-Dithiolane 164

5.22 1,3-Dithiole 165

5.23 1,3-Dithiolane 165

5.24 Oxazole 166

5.25 Benzoxazole 177

5.26 4,5-Dihydrooxazole 181

5.27 Isoxazole 185

5.28 4,5-Dihydroisoxazole 193

5.29 2,3-Dihydroisoxazole 198

5.30 Thiazole 199

5.31 Benzothiazole 208

5.32 Penam 212

5.33 Isothiazole 214

5.34 Imidazole 217

5.35 Benzimidazole 229

5.36 Imidazolidine 234

5.37 Pyrazole 236

5.38 Indazole 243

5.39 4,5-Dihydropyrazole 246

5.40 Pyrazolidine 249

5.41 1,2,3-, 1,2,4-, 1,3,4-Oxadiazole 249

5.42 1,2,5-Oxadiazole 251

5.43 1,2,3-Thiadiazole 254

5.44 1,2,4-Thiadiazole 256

5.45 1,2,3-Triazole 258

5.46 Benzotriazole 265

5.47 1,2,4-Triazole 268

5.48 Tetrazole 273

References 280

6 Six-Membered Heterocycles 297

6.1 Pyrylium Ion 297

6.2 2H-Pyran 305

6.3 2H-Pyran-2-one 306

6.4 3,4-Dihydro-2H-pyran 313

6.5 Tetrahydropyran 317

6.6 2H-Chromene 319

6.7 2H-Chromen-2-one 321

6.8 1-Benzopyrylium Ion 327

6.9 4H-Pyran 329

6.10 4H-Pyran-4-one 331

6.11 4H-Chromene 335

6.12 4H-Chromen-4-one 336

6.13 Chroman 341

6.14 Pyridine 345

6.15 Pyridones 381

6.16 Quinoline 386

6.17 Isoquinoline 406

6.18 Quinolizinium Ion 420

6.19 Dibenzopyridines 423

6.20 Piperidine 429

6.21 Phosphabenzene 434

6.22 1,4-Dioxin, 1,4-Dithiin, 1,4-Oxathiin 438

6.23 1,4-Dioxane 440

6.24 Oxazines 442

6.25 Morpholine 447

6.26 1,3-Dioxane 449

6.27 1,3-Dithiane 453

6.28 Cepham 455

6.29 Pyridazine 458

6.30 Pyrimidine 463

6.31 Purine 474

6.32 Pyrazine 481

6.33 Piperazine 486

6.34 Pteridine 487

6.35 Benzodiazines 491

6.36 1,2,3-Triazine 501

6.37 1,2,4-Triazine 504

6.38 1,3,5-Triazine 508

6.39 1,2,4,5-Tetrazine 512

References 517

7 Seven-Membered Heterocycles 529

7.1 Oxepin 529

7.2 Thiepin 532

7.3 Azepine 533

7.4 Diazepines 540

References 545

8 Larger Ring Heterocycles 547

8.1 Azocine 547

8.2 Heteronines and Larger-Membered Heterocycles 549

8.3 Tetrapyrroles 551

References 558

9 Problems and Their Solutions 561

References 614

Indices 621