The Chemistry of Heterocycles

Theophil Eicher studied chemistry at the University of Heidelberg and obtaind his PhD 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 Würzburg under Siegfried Hünig. 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, Saarbrücken, 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 PhD 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 fi eld 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, Saarbrücken. He obtained his PhD 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. 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

THE STRUCTURE OF HETEROCYCLIC COMPOUNDS

SYSTEMATIC NOMENCLATURE OF HETEROCYCLIC COMPOUNDS
Hantzsch-Widman Nomenclature
Replacement Nomenclature
Examples of Systematic Nomenclature
Important Heterocyclic Systems

THREE-MEMBERED HETEROCYCLES
Oxirane
Thiirane
2H-Azirine
Aziridine
Dioxirane
Oxaziridine
3H-Diazirine
Diaziridine

FOUR-MEMBERED HETEROCYLES
Oxetane
Thietane
Azete
Azetidine
1,2-Dioxetane
1,2-Dithiete
1,2-Dihydro-1,2-diazete
1,2-Diazetidine

FIVE-MEMBERED HETEROCYCLES
Furan
Benzo[b]furan
Isobenzofuran
Dibenzofuran
Tetrahydrofuran
Thiophene
Benzo[b]thiophene
Benzo[c]thiophene
2,5-Dihydrothiophene
Thiolane
Selenophene
Pyrrole
Indole
Carbazole
Isoindole
Indolizine
Pyrrolidine
Phosphole
1,3-Dioxolane
1,2-Dithiole
1,2-Dithiolane
1,3-Dithiole
1,3-Dithiolane
Oxazole
Benzoxazole
4,5-Dihydrooxazole
Isoxazole
4,5-Dihydroisoxazole
2,3-Dihydroisoxazole
Thiazole
Benzothiazole
Penam
Isothiazole
Imidazole
Benzimidazole
Imidazolidine
Pyrazole
Indazole
4,5-Dihydropyrazole
Pyrazolidine
1,2,3-, 1,2,4-, 1,3,4-Oxadiazole
1,2,5-Oxadiazole
1,2,3-Thiadiazole
1,2,4-Thiadiazole
1,2,3-Triazole
Benzotriazole
1,2,4-Triazole
Tetrazole

SIX-MEMBERED HETEROCYCLES
Pyrylium Ion
2H-Pyran
2H-Pyran-2-one
3,4-Dihydro-2H-pyran
Tetrahydropyran
2H-Chromene
2H-Chromen-2-one
1-Benzopyrylium Ion
4H-Pyran
4H-Pyran-4-one
4H-Chromene
4H-Chromen-4-one
Chroman
Pyridine
Pyridones
Quinoline
Isoquinoline
Quinolizinium Ion
Dibenzopyridines
Piperidine
Phosphabenzene
1,4-Dioxin, 1,4-Dithiin, 1,4-Oxathiin
1,4-Dioxane
Oxazines
Morpholine
1,3-Dioxane
1,3-Dithiane
Cepham
Pyridazine
Pyrimidine
Purine
Pyrazine
Piperazine
Pteridine
Benzodiazines
1,2,3-Triazine
1,2,4-Triazine
1,3,5-Triazine
1,2,4,5-Tetrazine

SEVEN-MEMBERED HETEROCYCLES
Oxepin
Thiepin
Azepine
Diazepines

LARGER RING HETEROCYCLES
Azocine
Heteronines and Larger-Membered Heterocycles
Tetrapyrroles

PROBLEMS AND THEIR SOLUTIONS