John A. Joule - Heterocyclic Chemistry

Contents

This edition first published 2010

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Library of Congress Cataloging-in-Publication Data

Joule, J. A. (John Arthur)

Heterocyclic chemistry / John A. Joule, Keith Mills. 5th ed.

p. cm.

Includes bibliographical references and index.

ISBN 978-1-4051-9365-8 (pbk.)-ISBN 978-1-4051-3300-5 (pbk.) 1. Heterocyclic chemistry. I. Mills, K. (Keith) II. Title.

QD400.J59 2009

547.59dc22

2009028759

ISBN Cloth: 978-1-405-19365-8

ISBN Paper: 978-1-405-13300-5

Preface to the Fifth Edition

Heterocyclic compounds have a wide range of applications but are of particular interest in medicinal chemistry, and this has catalysed the discovery and development of much heterocyclic chemistry and methods. The preparation of a fifth edition has allowed us to review thoroughly the material included in the earlier editions, to make amendments in the light of new knowledge, and to include recent work. Within the restrictions that space dictates, we believe that all of the most significant heterocyclic chemistry of the 20th century and important more recent developments, has been covered or referenced.

We have maintained the principal aim of the earlier editions to teach the fundamentals of heterocyclic reactivity and synthesis in a way that is understandable by undergraduate students. However, in recognition of the level at which much heterocyclic chemistry is now normally taught, we include more advanced and current material, which makes the book appropriate both for post-graduate level courses, and as a reference text for those involved in heterocyclic chemistry in the work place.

New in this edition is the use of colour in the schemes. We have highlighted in red those parts of products (or intermediates) where a change in structure or bonding has taken place. We hope that this both facilitates comprehension and understanding of the chemical changes that are occurring and, especially for the undergraduate student, quickly focuses attention on just those parts of the molecules where structural change has occurred. For example, in the first reaction below, only changes at the pyridine nitrogen are involved; in the second example, the introduced bromine resulting from the substitution and its new bond to the heterocycle, are highlighted. We also show all positive and negative charges in red.

In recognition of the enormous importance of organometallic chemistry in heterocyclic synthesis, we have introduced a new chapter dealing exclusively with this aspect. Chapter 4, Organometallic Heterocyclic Chemistry, has: (i) a general overview of heterocyclic organometallic chemistry, but most examples are to be found in the individual ring chapters, (ii) the use of transition metal-catalysed reactions that, as a consequence of a regularity and consistency that is to a substantial degree independent of the heterocyclic ring, is best treated as a whole, and therefore most examples are brought together here, with relatively few in the ring chapters.

Other innovations in this fifth edition are discussions in Chapter 5 of the modern techniques of: (i) solid-phase chemistry, (ii) microwave heating and (iii) flow reactors in the heterocyclic context. Reflecting the large part that heterocyclic chemistry plays in the pharmaceutical industry, there are entirely new chapters that deal with Heterocycles in Medicine (Chapter 33) and Heterocycles in Biochemistry; Heterocyclic Natural Products (Chapter 32).

We devote a new chapter (31) to some important topics: fluorinated heterocycles, isotopically labelled heterocycles, the use of bioprocesses in heterocyclic transformations, green chemistry and the somewhat related topic of ionic liquids, and some the applications of heterocyclic compounds in every-day life.