Chemistry of Heterocyclic Compounds: The Purines, Supplement 1, Volume 54

468 Pages·1996·21.07 MB·English

THE PURINES
Supplement 1
This is rhefifiy-fourth volume in the series
THE CHEMISTRY OF HETEROCYCLIC COMPOUNDS
~ ~~
THE CHEMISTRY OF HETEROCYCLIC COMPOUNDS
A SERIES OF
MONOGRAPHS
EDWARD C. TAYLOR, Editor
ARNOLD WEISSBERGER, Founding Edifor
THE PURINES
Supplement 1
John H. Lister
Former Senior Research Fellow
The Australian National University
Canberra, Australia
With an Essay by
M. David Fenn
Northern Territory University
Darwin, Australia
AN INTERSCIENCE@P UBLICATION
JOHN WILEY & SONS,
INC.
NEW YORK CHICHESTER BRISBANE TORONTO SINGAPORE
This text is printed acid-free paper.
on
Copyright Q 1996 by John Wiley & Sons, Inc.
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Reproduction or translation of any part of this work beyond
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information should be addressed to the Permissions Department,
John Wiley &Sons,I nc., 605 Third Avenue, New Y ork,
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Library of Congress Cataloging in Publication Data..
Lister, John Henry.
The purines. Supplement 1 I by John H.L ister ; with an essay by
David
M. Fenn.
p. cm.
“An Interscience publication.”
Includes index.
ISBN 0-471-08094-2 (cloth: alk. paper)
1. Purines. 1. Title.
.F96, pt. 2. Suppl.
QD401
547’.5966c20 9545002
I 0 9 8 7 6 5 4 3 2 1
DR. D. J. BROWN
An Appreciation
Although now retired, Des Brown, former Head of Medical Chemistry in the
John Curtin School of Medical Research, the Australian National University,
still retains an active involvement in the chemistry of pyrimidines and related
derivatives, which has been his major interest for over four decades. This com-
mitment is reflected in his authorship of the collected works, The Pyrimidines, in
the Heterocyclic Compoundr series and a further work in the same series,
Pteridines, which forms Part 3 of a composite Volume 24 devoted to Fused
Pyrimidines. To these achievements should be added his many contributions,
both practical and literary, to this important area of heterocyclic chemistry.
J.
H.L .
V
The Chemistry of Heterocyclic Compounds
Introduction to the Series
The chemistry of heterocyclic compounds constitutes one of the broadest and
most complex branches of chemistry. The diversity of synthetic methods utilized
in this field, coupled with the immense physiological and industrial significance of
heterocycles, combine to make the general heterocyclic arena of central impor-
tance to organic chemistry.
The Chemistry .f Heterocyclic Compounds, published since 1950 under the
initial editorship or Arnold Weissberger, and later, until Dr. Weissberger’s death
in 1984, under our joint editorship, has attempted to make the extraordinarily
complex and diverse field of heterocyclic chemistry as organized and readily
accessible as possible. Each volume has dealt with syntheses, reactions,
properties, structure, physical chemistry, and utility of compounds belonging to
a specific ring system or class (e.g., pyridines, thiophenes, pyrimidines, three-
membered ring systems). This series has become the basic reference collection for
information on heterocyclic compounds.
Many broader aspects of heterocyclic chemistry are recognized as disciplines
of general significance which impinge on almost all aspects of modern organic and
medicinal chemistry, and for this reason we initiated several years ago a parallel
series entitled General Heterocyclic Chemistry, which treated such topics as
nuclear magnetic resonance, mass spectra, photochemistry of heterocyclic
compounds, the utility of heterocyclic compounds in organic synthesis, and the
synthesis of heterocyclic compounds by means of 1,3-dipolar cycloaddition
reactions. These volumes are of interest to all organic and medicinal chemists, as
well as to those whose particular concern is heterocyclic chemistry.
It has become increasingly clear that this arbitrary distinction created as many
problems as it solved, and we have therefore elected to discontinue the more
recently initiated series General Heterocyclic Chemistry and to publish all forth-
coming volumes in the general area of heterocyclic chemistry in The Chemistry of
Heterocyclic Compoundr series.
As Dr. Lister has stated so cogently in his Preface, this Supplement is indeed
intended to be precisely that-an additionkxpansion to his previous volume on
purine chemistry, which appeared as Vol. 24, Part I1 in the present series in 197 1.
A deliberate attempt has been made to concentrate on updating those areas of
purine chemistry that, in the author’s judgment, merit discussion on the basis of
utility, novelty, or fundamental interest. Readers should therefore note that
Volume 24, Part and the present Supplement together constitute a rigorous
I1
and fairly exhaustive treatment of purine chemistry; either volume alone would
Vii
...
Vlll Introduction to the Series
be inadequate. Dr. Lister is to be commended for his lucid and beautifully orga-
nized presentation of an extremely active field that is of immense interest to both
chemistry and biology.
Department of Chrmistry EDWARDC .T AYLOR
Princeton Universiry
Princeton, New Jersey
At any point in time, a subject can be reviewed in the light of its past, present,
and future perspectives. In this supplementary volume to the original, which
appeared in 1971, the basic aim is to explore the first two of these aspects and to
indicate possible future trends or developments. The major emphasis in the par-
ent volume centered on the synthetic approaches available, but in the two decades
since its publication a shift away from these has been noted. More emphasis is now
being placed on investigations of the nature and reactions of the purine system.
New or improved syntheses continue to appear; in many cases the introduction
of novel and sometimes esoteric reagents enables these previously unattainable
preparations to be made. Because of their ubiquitous distribution, naturally
occurring purines continue to attract the interest of workers in diverse scientific
disciplines, with significant data being disseminated over an ever-proliferating
number of journals. In an attempt to survey the literature, a selective approach
has been adopted in this volume, and the reader’s forgiveness is sought if a point
of particular interest appears to have been overlooked. One aspect of this is seen
in comparison of the chapter contents with those of the parent volume; the omis-
sion of a particular section or topic indicates that significant or novel features have
not been noted.
In a work of this nature, the author can only be one of the players, and the final
outcome is the result of many efforts, large and small. I wish to record my deep
appreciation to Wilf Amarego for so elegantly producing the majority of the for-
mulas; these were supported by supplementary onesdrawn by Maxine Tyler. I am
also grateful to David Fenn for contributing a timely exposition of the present
state of the NMR of purine derivatives; this work fills a gap in the current litera-
ture. The interest and encouragement expressed by my colleagues during the
preparation of this volume has been most gratifying; in particular, the support of
Des Brown has been greatly valued. It would be remiss of me not to acknowledge
the patience and forbearance shown by Professor E. C. Taylor as editor who, like
the policeman in the Pirates of Penzance, does not have a happy lot when dealing
with tardy authors. I owe a special debt to Mandi Weymes, who carried out the
onerous task of transforming the rough copy to the final printout with great
cheerfulness. My thanks are also given to the llniversity of Hull for the use of the
library and to Kathy Rabl of the Australian National University for her kind-
ness in obtaining the photograph of Dr. Brown. Lastly, a special “thank you”
goes to my wife, June, and children, Catherine and David, for all their help and
support, in many ways, throughout the writing process.
KirkeIIa. England JOHNH . LISTER
ix
Contents
List of Tables xiii
1. Introduction to the Purines (HI) 1
11. Synthesis from Pyrimidines 21
111. Purine Syntheses from Imidazoles and Other Precursors 61
(H91)
IV. Purine and C-Alkyl, C-Aryl, and N-Alkyl Derivatives (HI 17) 83
V. Halogenopurines (HI 99
35)
VI. 0x0-(Hydroxy-) and Alkoxypurines (H203) 133
VII. Thioxo- and Selenoxopurines and Derivatives (H269) 179
MII. The Amino (and Amino-0xo)purines (H309) 213
IX. The Purine Carboxylic Acids and Related Derivatives (H367) 283
X. Nitro-, Nitroso-, and Arylazopurines (H401) 303
XI. Purine-N-Oxides (H409) 307
XII. The Reduced Purines (H427) 325
XIII. Enlarged Purine-Containing Structures (New) 337
XIV. The Spectra of Purines (H507) 347
xv.
Systematic Tables of Simple Purines 385
REFERENCES 425
INDEX 455
xi
List of Tables
TABLE 1 Trivial Names of Purines 3
TABLE 2 8-Thioxopurines Derived from Ring Closures with
Carbon Disulfide 37
TABLE 3 Uric Acid Derivatives Derived from Alkyl
Chlorocarbonate Cyclizations 38
TABLE 4 Examples of Approaches Used to Form 7- and 9-Alkyl
Derivatives of Halogenopurines 131
TABLE 5 Alkylation of Theophylline and Other I ,3-Dialkyl-
xanthines to 1,3,7-Trialkylxanthines 154
TABLE 6 Examples of 8-Thioxopurine Formation by the Traube
Reaction with 4,5-Diaminopyrimidines 181
TABLE 7 Alkylation of Adenine Under Phase-Transfer Catalysis
Conditions 257
TABLE 8 Examples of Approaches Used for N-Alkylation of
Adenines 257
TABLE 9 Examples of 7- and 9-Alkylation of Guanines 260
TABLE 10 I H Spectra of Some Simple Purines 349
TABLE 11 Spectra of Some Simple Purines 363
TABLE 12 IS N Spectra of Simple Purines 369
TABLE 13 References for Nitrogen Chemical Shifts 37 0
TABLE 14 Alkyl and Aryl Purines 387
TABLE 15 C- and N-Alkyl and Aryl Adenines 388
TABLE 16 Other Aminopurines Including N-Aminopurines 390
...
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