Chemistry of Heterocycles

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 ixAbbreviations and Symbols xi1 The Structure of Heterocyclic Compounds 1Reference 42 Systematic Nomenclature of Heterocyclic Compounds 52.1 Hantzsch-Widman Nomenclature 62.2 Replacement Nomenclature 112.3 Examples of Systematic Nomenclature 122.4 Important Heterocyclic Systems 153 Three-Membered Heterocycles 173.1 Oxirane 173.2 Thiirane 263.3 2H-Azirine 293.4 Aziridine 323.5 Dioxirane 373.6 Oxaziridine 383.7 3H-Diazirine 403.8 Diaziridine 40References 414 Four-Membered Heterocyles 454.1 Oxetane 454.2 Thietane 494.3 Azete 504.4 Azetidine 514.5 1,2-Dioxetane 554.6 1,2-Dithiete 574.7 1,2-Dihydro-1,2-diazete 584.8 1,2-Diazetidine 58References 595 Five-Membered Heterocycles 615.1 Furan 615.2 Benzo[b]furan 805.3 Isobenzofuran 845.4 Dibenzofuran 865.5 Tetrahydrofuran 875.6 Thiophene 905.7 Benzo[b]thiophene 1015.8 Benzo[c]thiophene 1045.9 2,5-Dihydrothiophene 1055.10 Thiolane 1065.11 Selenophene 1075.12 Pyrrole 1085.13 Indole 1255.14 Carbazole 1485.15 Isoindole 1505.16 Indolizine 1525.17 Pyrrolidine 1575.18 Phosphole 1615.19 1,3-Dioxolane 1625.20 1,2-Dithiole 1635.21 1,2-Dithiolane 1645.22 1,3-Dithiole 1655.23 1,3-Dithiolane 1655.24 Oxazole 1665.25 Benzoxazole 1775.26 4,5-Dihydrooxazole 1815.27 Isoxazole 1855.28 4,5-Dihydroisoxazole 1935.29 2,3-Dihydroisoxazole 1985.30 Thiazole 1995.31 Benzothiazole 2085.32 Penam 2125.33 Isothiazole 2145.34 Imidazole 2175.35 Benzimidazole 2295.36 Imidazolidine 2345.37 Pyrazole 2365.38 Indazole 2435.39 4,5-Dihydropyrazole 2465.40 Pyrazolidine 2495.41 1,2,3-, 1,2,4-, 1,3,4-Oxadiazole 2495.42 1,2,5-Oxadiazole 2515.43 1,2,3-Thiadiazole 2545.44 1,2,4-Thiadiazole 2565.45 1,2,3-Triazole 2585.46 Benzotriazole 2655.47 1,2,4-Triazole 2685.48 Tetrazole 273References 2806 Six-Membered Heterocycles 2976.1 Pyrylium Ion 2976.2 2H-Pyran 3056.3 2H-Pyran-2-one 3066.4 3,4-Dihydro-2H-pyran 3136.5 Tetrahydropyran 3176.6 2H-Chromene 3196.7 2H-Chromen-2-one 3216.8 1-Benzopyrylium Ion 3276.9 4H-Pyran 3296.10 4H-Pyran-4-one 3316.11 4H-Chromene 3356.12 4H-Chromen-4-one 3366.13 Chroman 3416.14 Pyridine 3456.15 Pyridones 3816.16 Quinoline 3866.17 Isoquinoline 4066.18 Quinolizinium Ion 4206.19 Dibenzopyridines 4236.20 Piperidine 4296.21 Phosphabenzene 4346.22 1,4-Dioxin, 1,4-Dithiin, 1,4-Oxathiin 4386.23 1,4-Dioxane 4406.24 Oxazines 4426.25 Morpholine 4476.26 1,3-Dioxane 4496.27 1,3-Dithiane 4536.28 Cepham 4556.29 Pyridazine 4586.30 Pyrimidine 4636.31 Purine 4746.32 Pyrazine 4816.33 Piperazine 4866.34 Pteridine 4876.35 Benzodiazines 4916.36 1,2,3-Triazine 5016.37 1,2,4-Triazine 5046.38 1,3,5-Triazine 5086.39 1,2,4,5-Tetrazine 512References 5177 Seven-Membered Heterocycles 5297.1 Oxepin 5297.2 Thiepin 5327.3 Azepine 5337.4 Diazepines 540References 5458 Larger Ring Heterocycles 5478.1 Azocine 5478.2 Heteronines and Larger-Membered Heterocycles 5498.3 Tetrapyrroles 551References 5589 Problems and Their Solutions 561References 614Indices 621