Heterocyclic Chemistry: Volume I: Principles, Three- and Four-Membered Heterocycles PDF
Preview Heterocyclic Chemistry: Volume I: Principles, Three- and Four-Membered Heterocycles
Heterocyclic Chemistry I Heterocyclic Chemistry R. R. Gupta, M. Kumar, V. Gupta VolmneI: Principles, 1bree-and Four-Membered Heterocycles Volmne II: Five-Membered Heterocycles Volmne ill: Six-Membered and Higher Heterocycles Springer Berlin Heidelberg New York Barcelona Budapest Hong Kong London Milan Paris Singapur Tokyo R. R. Gupta, M. Kumar, V. Gupta Heterocyclic Chemistry Volume I: Principles, Three-and Four-Membered Heterocycles With 98 Figures and 34 Tables , Springer Prof. Radha Raman Gupta Dr. Mahendra Kumar Dr. VandanaGupta Department of Chemistry University of Rajasthan Jaipur-302004 / India ISBN-I3:978-3-642-72278-3 e-ISBN-I3:978-3-642-72276-9 001: 10.1007/978-3-642-72276-9 Die Deutsche Bibliothek - CIP-Einheitsaufnahme Gupta, Radha R.: Heterocyclic chemistry / R. R. Gupta; M. Kumar; V. Gupta. - Berlin; Heidelberg; New York; Barcelona; Hong Kong; London; Milan; Paris; Singapur; Tokyo : Springer Vol. 1. Principles, three- and four-membered heterocycles: with 34 tables. - 1998 ISBN -13: 978-3-642-72278-3 CIP data applied for This work is subject to copyright. All rights are reserved, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilm or in other ways, and storage in data banks. Duplication of this publication or parts thereof is permitted only under the provisions of the German Copyright Law of September 9, 1965, in its current version, and permission for use must always be obtained from Springer-Verlag. Violations are liable for prosecution act under German Copyright Law. © Springer-Verlag Berlin Heidelberg 1998 Softcover reprint of the hardcover 1st edition 1998 The use of general descriptive names, registered names, trademarks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. Typesetting: Camera ready by authors Cover: E. Kirchner, Heidelberg SPIN:I0100048 66/3020 -5 4 3 2 1 0 - Printed on acid-free paper FOREWORD Today, our world increasingly is conceived ofa s being molecular. An ever widening range ofp henomena are described logically in terms ofm olecular properties and molecular interactions. The majority ofk nown molecules are heterocyclic and heterocycles dominate the fields of biochemistry, medicinal chemistry, dyestuffs, photographic science and are ofi ncreasing importance in many others, including polymers, adhesives, and molecular engineering. Thus, the importance ofh eterocyclic chemistry continues to increase and this three volume work by Drs. R. R. Gupta, Mahendra Kumar and Vandana Gupta is a welcome addition to the available guides on the subject. Its scope places it in a useful niche between the single-volume texts and monographs ofh eterocyclic chemistry and the multivolume treatises. The authors have retained the well tried classical approach but have succeeded in placing their own individual spin on their arrangement. They have put together a well selected range from among the most important oft he vast array offacts available. This factual material is ordered in a clear and logical fashion over the three volumes. The present work should be ofg reat value to students-and practitioners ofh eterocyclic chemistry at all levels from the advanced undergraduate upwards. It will be ofp articular assistance in presenting a clear and modem view of the subject to those who use heterocycles in a variety of other fields and we wish it well. Alan R. Katritzky April 1998 University ofF lorida PREFACE Our aim is to bring out a text-cum-reference book on heterocyclic chemistry for undergraduate and graduate students, and research workers who wish to choose heterocyclic chemistry in their research careers. This will enable them to have a comprehensive knowledge oft he syntheses, properties, reactions and their mechanisms and applications ofh eterocyclic compounds. Efforts have been made to include recent developments in heterocyclic chemistry and the subject is presented in a simple and lucid manner, so that those who have some background knowledge of organic chemistry can understand it well. For the sake of convenience, subject matter covered in heterocyclic chemistry has been divided into three volumes: Volume I: Principles, Three-and Four-Membered Heterocycles Introduction Nomenclature ofH eterocycles Aromatic Heterocycles Nonaromatic Heterocycles Heterocyclic Synthesis Three-Membered Heterocycles Four-Membered Heterocycles Volume II: Five-Membered Heterocycles Introduction Five-Membered Heterocycles with One Heteroatom Benzo-Fused Five-Membered Heterocycles with One Heteroatom Five-Membered Heterocycles with Two Heteroatoms Five-Membered Heterocycles with More Than Two Heteroatoms Meso-Ionic Heterocycles VIII Volume ill: Six-Membered and Higher Heterocycles Introduction Six-Membered Heterocycles Seven-Membered Heterocycles Large Ring Heterocycles Photochemistry ofH eterocycles Since there are detailed contents at the beginning of each chapter, the details for individual chapters are not given here. We have :freely consulted edited scientific works such as Comprehensive Heterocyclic Chemistry edited by A.R. Katritzky and C.W. Rees, Advances in Heterocyclic Chemistry edited by A.R. Katritzky and the Chemistry of Heterocyclic Compounds edited by A. Weissberger and E.C. Taylor. We are very grateful to editors, authors and publishers of these works. We express our thanks to our colleagues and Ph.D. students who assisted us in proof reading and in several other ways. Our sincere thanks are also due to Dr. R. Stumpe and Dr. Joe P. Richmond editors at Springer Verlag for providing valuable suggestions for the preparation oft he book. Jaipur, India R.R. Gupta April, 1998 Mahendra Kumar Vandana Gupta Symbols and Abbreviations Bond angle distortion or deviation / Coulomb integral (as stated) A Karplus constant AIBN 1; 2,2'-Azobisisobutyronitrile ~ Resonance integral Wave length conc. Concentrated DE Delocalization energy DRE Dewar resonance energy A Diamagnetic susceptibility exaltation AO(Dae) Chemical shift difference DIBAL Diisobutylaluminium hydride Dil. Diluted DMF N,N-Dimethylfonnamide DMSO Dimethyl sulfoxide E Bond angle strain / Torsional energy (as stated) ERE Empirical resonance energy Eu(fodh Tris-( 6,6, 7,7 ,8,8,8-heptatluoro-2,2-dimethyl-3 ,5-octanedionato ) europium Extinction coefficient Conformational free energy Free energy of activation Enthalpy difference between conformers AH Heat offo rmation (exp.) HMPAlHMPT Hexamethylphosphoric triamide HOMO Highest occupied molecular orbital Band intensity in vibrational spectra for axial and equatorial conformers x J Coupling cosntant Kc Rate of ring inversion Ke Equilibrium constant of interconvertible conformers Ke Bond bending force constant A. Wave number IDA Lithium diisopropylamide LTA Lead tetraacetate LUMO Lowest unoccupied molecular orbital MCPBA m-Chloroperbenzoic acid NBS N-Bromosuccinimide hv Photochemical run Nanometer (1 o-~ N-PSP N-Phenylselenophthalimide pm Picometer (10-12) PPA Polyphosphoric acid R Coupling constants ratio REPE Resonance energy per x-electron \II Internal torsional angle Tc Coalescence temperature TCNE Tetracyanoethylene tert Tertiary TFAA Tritluoroacetic anhydride THF Tetrahydrofuran 1HP Tetrahydropyran a Dihedral angle TMEDA N,N,N,N-Tetramethylenediamine Tos / Tosyl p-Toluenesulfonyl VR Vilsmeier reagent 0) Dihedral angle deviation Diamagenetic susceptibility CONTENTS Chapter 1. Introduction 1 Chapter 2. Nomenclature of Heterocycles 3 Chapter 3. Aromatic Heterocycles 39 Chapter 4. Nonaromatic Heterocycles 105 Chapter 5. Heterocyclic Synthesis 159 Chapter 6. Three-Membered Heterocycles 275 Chapter 7. Four-Membered Heterocycles 357 Subject Index 411
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