Heterocyclic Chemistry

by Sainsbury, Malcolm; Phillips, David; Abel, E. W.; Woollins, J. Derek

• ISBN13: 9780854046522
• ISBN10: 0854046526
• Format: Paperback
• Copyright: 2001-10-10
• Publisher: Royal Society of Chemistry

Summary

This book deals with the fundamental chemistry of fully saturated and unsaturated 4-, 5- and 6-membered heterocycles. The principal focus is those compounds containing a single nitrogen, oxygen or sulfur atom and by restricting discussion to these, a balanced treatment is possible. The book introduces a selection of important heterocyclic compounds and the vital role that they play in life, medicine and industry. Conformational aspects of heterocyclic chemistry, aromatic stabilization, nomenclature, reaction mechanisms and methods of synthesis are also discussed. Ideal for the needs of undergraduate chemistry students, Tutorial Chemistry Texts is a major series consisting of short, single topic or modular texts concentrating on the fundamental areas of chemistry taught in undergraduate science courses. Each book provides a concise account of the basic principles underlying a given subject, embodying an independent-learning philosophy and including worked examples.

Table of Contents

Introduction to Heterocyclic Chemistry	p. 1
Coverage	p. 1
Nomenclature	p. 1
Importance to Life and Industry	p. 4
General Principles	p. 6
Pyridine	p. 18
Resonance Description	p. 18
Electrophilic Substitution	p. 19
Pyridine N-Oxides	p. 22
Nucleophilic Substitution	p. 23
Lithiation	p. 28
Methods of Synthesis	p. 28
Commonly Encountered Pyridine Derivatives	p. 29
Reduced Pyridines	p. 36
Benzopyridines	p. 42
Introduction	p. 42
Quinoline	p. 43
Isoquinoline	p. 50
Pyrylium Salts, Pyrans and Pyrones	p. 58
Introduction	p. 58
Pyrylium Salts	p. 59
Pyran-2-ones ([alpha]-Pyrones)	p. 61
Pyran-4-ones ([gamma]-Pyrones)	p. 63
Reduced Pyrans	p. 65
Saccharides and Carbohydrates	p. 65
Benzopyrylium Salts, Coumarins, Chromones, Flavonoids and Related Compounds	p. 68
Structural Types and Nomenclature	p. 68
Coumarins	p. 70
Chromones (Benzopyran-4-ones)	p. 72
Five-membered Heterocycles containing One Heteroatom: Pyrrole, Furan and Thiophene	p. 77
Pyrrole	p. 77
Furan	p. 85
Thiophene	p. 91
Benzo[b]pyrrole, Benzo[b]furan and Benzo[b]thiophene	p. 97
Indole (Benzo[b]pyrrole)	p. 97
Benzo[b]furan and Benzo[b]thiophene	p. 110
Four-membered Heterocycles containing a Single Nitrogen, Oxygen or Sulfur Atom	p. 115
Azete, Azetine and Azetidine	p. 115
Oxetene and Oxetane	p. 121
Thietene and Thietane	p. 122
Answers to Problems	p. 125
Subject Index	p. 141
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