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Azolides in Orgpnic Synthesis and Biochemistry. H. A. Staab, H. Bauer, K. M. Schneider

ISBNs: 3-527-29314-0 (Hardback); 3-527-60083-3 (Electronic)

Azolides in Organic Synthesis

and Biochemistry

WILEY-VCH

Azolides in Organic Synthesis

and Biochemistry

H. A. Staab H. Bauer K. M. Schneider

Abteilung Organische Chemie

Max-Planck Institutfur Medizinische Forschung

Heidelberg

WILEY-VCH

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Deutsche Bibliothek Cataloguing-in-Publication Data

Staab, Heinz A.:

Azolides in organic synthesis and biochemistry / H. A. Staab; H.

Bauer; K. M. Schneider. - Weinheim; Berlin; Chichester;

New York; Brisbane; Singapore; Toronto: Wiley-VCH, 1998

ISBN 3-527-29314-0

British Library Cataloguing in Publication Data

A catalogue record for this book is available from the British Library

ISBN 3-527-29314-0

Typeset in 10/12pt Times from author's disks by Techset, Salisbury

Printed and bound in Great Britain by Bookcraft (Bath) Ltd

This book is printed on acid-free paper responsibly manufactured from sustainable forestation,

for which at least two trees are planted for each one used for paper production

Preface

Preparation, properties and the manifold synthetic applications of "azolides" in

organic and bioorganic chemistry are the topics of this book. Azolides like the N-acyl,

W-sulfonyl and AT-phosphoryl derivatives of imidazoles, triazoles, tetrazoles, benz-

imidazoles and benzotriazoles represent an easily accessible class of activated acid

derivatives, the distinct and gradually varied reactivity of which makes them especially

useful for a wide variety of synthetic reactions. The systematic investigation and

expansion of this group of compounds, as well as its introduction into synthetic

chemistry, are based almost exclusively on syntheses, reactivity studies, and pre-

parative developments introduced in our laboratory during the decade from the mid-

50s to the mid-60s. Of special importance for the synthetic application of azolides was

my synthesis in 1956 of TV^/V'-carbonyldiimidazole (CDI), followed by its analogues

which as highly reactive reagents paved the way to a variety of new reactions. CDI still

remains the most used compound in azolide syntheses.

A first review of our work in this field was published under the title "Syntheses

Using Heterocyclic Amides (Azolides)" in Angewandte Chemie in 1962; an updated

version co-authored by W. Rohr was included in Vol. V of the series Newer Methods of

Preparative Organic Chemistry (Verlag Chemie, Weinheim 1967). Since then, how-

ever, azolide reactions, due to their versatility, ease of handling, and mild reaction

conditions, have become widely used in very diverse fields of chemistry and bio-

chemistry, as will be shown in this book.

After conceiving and working out most of the basic types of azolide reactions, our

own group left this field completely more than 25 years ago to become engaged in

quite different areas of organic chemistry. Nevertheless, we followed with interest the

further growth of my first "scientific baby", and we note with satisfaction the wide

scope within which azolide reactions are now being applied and continue to be

introduced for new synthetic purposes. Under these circumstances we felt that a

comprehensive account of azolide reactions with emphasis on their application in

organic and bioorganic synthesis was overdue.

We soon found out that the material we had to deal with was much more extensive

than we had anticipated. It was necessary to evaluate several thousands of papers

dealing with azolide reactions in recent years. Chemical Abstracts lists more than 1500

references to CDI alone from 1967 to the present. Thus, what was originally planned

as a progress review chapter in one of the existing series on organic reactions grew up

into a real book, which we hope to be of value to organic chemists and biochemists

interested in synthetic methods.

Preface

This book never would have been completed without the enthusiastic engagement

of my co-authors Professor Helmut Bauer and Ms. Karin M. Schneider, whom I would

like to thank for the great effort they devoted to this project, their careful collecting

and evaluating of the extensive material, and their excellent achievement in preparing

and drafting most of the manuscript. We also thank Ms. Anke Friemel for her out-

standing word-processing and editing of chemical structures and equations.

Heinz A. Staab

Heidelberg, January 1998

Azolides in organic synthesis & biochemistry - Staab.pdf

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