The Chemistry of Heterocycles

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, Speicher 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

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
5.9 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

• By (author) Theophil Eicher
• By (author) Siegfried Hauptmann
• By (author) Andreas Speicher