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PYRIDINE and ITS DERIVATIVES Part Five PYRIDINE AND ITS DERIVATIVES Part Five Edired by George R. Newkome Louisiana State University Baton Rouge. Louisiana AN INTERSCIENCE "I PUBLICATION John Wiley and Sons NEWYORK CHICHESTER BRISBANE TORONTO SINGAPORE ______I_ ----__ll____l_________.__ __I____II___-_-.----c.__. I_ _____X_I__._-.--.--_ PYRIDINE AND ITS DERIVATIVES Part Five This is the jourteetith iw/ut?ii, in the siviips THE CHEMISTRY OF HETEROCYCLIC COMPOUNDS - - __- .-.-___*-l_ll_---.-----_ ___- -- TItE CHEMISTRY OF HETEROCYCLIC COMPOUSDS A SERIES OF MONOGRAPHS ARNOLD WEISSBERGKR AND EDWARD C. TAYLOR @ PYRIDINE AND ITS DERIVATIVES Part Five Edired by George R. Newkome Louisiana State University Baton Rouge. Louisiana AN INTERSCIENCE "I PUBLICATION John Wiley and Sons NEWYORK CHICHESTER BRISBANE TORONTO SINGAPORE ______I_ ----__ll____l_________.__ __I____II___-_-.----c.__. I_ _____X_I__._-.--.--_ An Interdencc " PUbllCdtioll Copyright @ 1984 hy John Wiley & Sons. Inc. All rights rewved. Puhlished simultaneously in Canada. Keproductioii or translalion of any part of this work beyond that permitied by Section 107 or 108 ofthe 1976 United States Copyright Act without the permission of ihe copyright owner is unlawful. Requests for permishn or further information should be addreshed to the Periniwons Department. John Wiley & Sons. Ins. Library of Congrclr.5 catabging in Publication Data : ( Revid Ibr volume 5) Klingsberg. Erwin. Pyridine and it\ derivatives. (The Cheniislr) of heteroc)clic ccimpound>: a ,cries of nionographs. v. 14) Vd. 5- edited hy George R. Newkoiiir Vd. 5- ha3 impriiir : New York : Wile! "An Interscience publication" -Val. 5. I p Include\ hihl iograph ics. I. Plridiiie. I. Ncwkoine. George R. (George Kizh.irdI II. Title. Ill. Serie\: Chemistry of heieroc?clic compound>.\. 14. QD4Oi.K712 547'.5Y3 59-13038 ISBN 0-471-05072-5 (v. 5) 10 9 K 7 6 5 4 3 2 i Contributors T. D. BAILEY J. D. SAUER Reilly Tar and Chemical Corporation Ethyl Corporation Indianapolis, Inilianu Baton Rouge, Louisiana G. L. GOE E. F. V. SCRIVEN Reilly Tar and Chemical Corporation Reilly Tar and Chemical Corporation Indiunapolis, Indianu Indiarwpolis, Indiana V. K. GUPTA R. P. THUMMEL Depa r ttnen t of' Clierii is try Depar frnent 01' Client istry Louisiana Stute Uniwrsity Unicersity of' Houston Baton Roicyr, Louisium Houston. Trsas G. R. NEWKOME Department of Clietnistry Louisiana Stare Unioersitj Baton Rouge, Louisiarru Tbe Chemistry of Heterocyclic Compounds The chemistry of heterocyclic compounds is one of the most complex branches of organic chemistry. It is equally interesting for its theoretical implications. for the diversity of its synthetic procedures, and for the physiological and industrial significance of heterocyclic compounds. A field of such importance and intrinsic difficulty should be made as readily accessible as possible, and the lack of a modern detailed and comprehensive presentation of heterocyclic chemistry is therefore keenly felt. It is the intention of the present series to fill this gap by expert presentations of the various branches of heterocyclic chemistry. The subdivisions have been designed to cover the field in its entirety by monographs which reflect the importance and the interrelations of the various compounds, and accommodate the specific interests of the authors. In order to continue to make heterocyclic chemistry as readily accessible as possible, new editions are planned for those areas where the respective volumes in the first edition have become obsolete by overwhelming progress. If, how- ever, the changes are not too great so that the first editions can be brought up-to-date by supplementary volumes, supplements to the respective volumes will be published in the first edition. Researcli Lubornrories ARNOLDWEISSBERGER hsmmKoahk Compnny Roclrester, New York Princeton Uiiiixvsify EDWARDC. TAYLOR Princeton, New Jersey vii Preface The original four volumes of this pyridine series were published between 1960 and 1964 under the guidance of Dr. Erwin Klingsberg. In 1974-1975, Professor Rudy Abramovitch edited a four-volume supplemental series, which followed the general format of the initial work. These herculean tasks covered most of the important research in pyridine chemistry up to 1970-1972. As with most areas of organic chemistry, proliferation has occurred at an incredible rate, especially in heterocyclic chemistry. The need for a topical update in key research areas is essential ; thus, the supplemental series has changed format in order to keep the interest in pyridine chemistry as current as possible. In 1977, Professor Abramovitch and I discussed the creation of this ex- pansion of Pyridine and Its Derivatiues and decided to abandon the difficuli- to-organize chapter order of the previous volumes in this series. Also, new topics and directions caused duplication and a need for new chapters to meet the ever-expanding field of pyridine chemistry. As the task started, Professor Abramovitch’s writing and editing obligations in other areas of interest pre- vented his devotion to this series; his efforts are sorely missed. This and all future supplementary volumes in the Pyridine and Its Derimriucs series will be devoted to specific areas of interest and will attempt to remain as the comprehensive repository of pyridine chemistry. I express my thanks to the authors for their contributions and patience as well as to Rudy Abramovitch for his initial guidanceand support in this project. GEORGER. NEWKOME ix Contents I. SYNTHETIC AND NATURAL SOURCES OF THE 1 PYRIDINE RING T. D. BAILEY,G. L. GOE,and E. F. V. SCRIVEN 11. CARBOCYCLIC ANNELATED PYRIDINES 253 R. P. THUMMEL 111. MACROCYCLIC PYRIDINES 447 G. K. NEWKOME,V. K. GUPTA,and J. D. SAUER IV. THE REVIEWS OF PYRIDINE CHEMISTRY-11968-1982 635 G. R. NEWKOME AUTHOR INDEX 659 SUBJECT INDEX 703 xi PYRlDlNE AND ITS DERIVATIVES Part Five This is tl~efourttwi~liIohtnrc it1 [lie .seric.y THE CHEMISTRY OF HETEROCYCLIC COMPOUNDS CHAPTER I Synthetic and Natural Sources of the Pyridine Ring T. D. BAILEY, G.L. COE, and E. F. V. SCRIVEN Reilly Tar and Chemical Corporation, Indianapolis, Indiona I. Pyridines from Natural Sources ............... 3 1. Pyridines in Nature ................ .. 3 A. Enzymes, Vitamins, Amino Acids, and Their Biogenesis ...... 3 B. The Tobacco Alkaloids. ............... I C. Other Pyridine Alkaloids and Related Compounds ...... .. 11 a. Simple Pyridine Alkaloids .............. 11 b. Monoterpenoid Alkaloids .............. 12 c. Scsquiterpenoid Alkaloids ........... .. 16 i. Derivatives of Nicotinic Acid .......... .. 16 ii. Pyridone and Pyridinol Alkaloids. .......... 11 iii. Other Sesquiterpcnoid Alkaloids ......... .. 22 d. pCarboline and Related Alkaloids That Contain a Pyridinc Ring. .. 23 2. Degradation of Natural Products .............. 24 A.Coa1. .................... 24 B. Petroleum ................. .. 28 C. Shale. .................... 29 D. Degradation and Transformation of Alkaloids ......... 31 E. Flavors, Odors, and Volatile Constituents of Food and Beverages . .. 33 F. Miscellaneous Sources .............. .. 36 11. Pyridines by Synthetic Methods ............... 36 1. From Other Ring Systcms .............. .. 36 A. Carbocyclic Compounds ............... 31 B. Three-Membered Ring Heterocycles .......... .. 43 C. Four-Membered Ring Heterocycles ............ 46 D. Five-hlcrnbered Ring Heterocyclcs ............ 41 a. Five-Membered Rings Containing One Ileteroatom .... .. 48 i. Furans, Dihydrofurans, and Tetrahydrofurans ..... .. 48 ii. Pyrroles ................ .. 55 b. Five-Membered Rings Containing Two Heteroatoms .... .. 60 i. Oxazoles. ............... .. 60 ii. Miscellaneous Fivc-hlembered Ring Hetcrocycles .... .. 68 E. Six-Mcmbered Ring Heterocycles. .......... .. I5 a. One Heteroatom .............. .. I5 i. Pyrones ................ .. I5 1 2 'r . D . Bailcy, C . L . Goe. and E . F . V . Scriven ii . Pyrcins .................. 83 iii . Pyrylium Salts ................ 83 b . Two Hetcroatoms ................ 93 i . Pyriniidincs ................. 93 ii. Pyridazincs ................. 97 iii . Pyrazincs .................. 98 iv. Oxmincs .................. 99 v . Miscellancous Six-hiembered Heterocycles Containing Two ... lleteroatonis ................ 101 c . Six-Membcrcd Ring lleterocycles with Tluec tietcroatoms .... 102 F . Seven-Membered Ring lieterocycles ............ 104 a . Azepincs .................. 104 b . Diazepincs .................. 105 G . Pyridincs from Reduced Pyridines ............ 106 a . Dihydropyridines ................ 106 b . Tctrahydropyridincs ............... 111 c. Piperidines .................. 113 H . Condensed Kinps ................. 113 a . Oxidation .................. 113 b . Reductions .................. 117 c . RingOpcning Reaction .............. 117 2 . From Acyclic Compounds. ............... 118 A . Cyclization of a 5Carbon Chain ............. 119 a . 1 J-Dioxo Compounds and Derivatives .......... 119 b . Oxocarboxylic Acids and Derivatives ........... 125 c . 1 .5-Dicarboxylic Acids and Derivatives .......... 132 d . Conipounds Having Terminal Unsaturation ......... 136 e . Misccllaneous 1.5.Bifunctional Compounds ......... 139 B. 4-1 Condcnxitit>ns ................. 141 a . Dicncs with Nitrilcs ............... 141 b . Other Rc;ictions of Nitrilcs ............. 142 c . Reactionr of lsocyanates .............. 144 d . Reaction of Othcr Acid Derivativcs ........... 144 e . Miscellaneous ................. 146 C . 3-2 Condcnsations ................. 147 a . 1.3-Dicarbonyl Cumpounds and Their Derivatives wit11 Methylenic . Compuunds .................
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