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Name Reactions in Heterocyclic Chemistry

Author(s): Editor: Jie Jack Li (Pfizer Global Research and Development in Ann Arbor, Michigan)
ISBN10: 0471302155
ISBN13: 9780471302155
Cover: Hardcover
 
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SummaryTable of ContentsAuthor BiographyEditorial Reviews
Covers important name reactions relevant to heterocyclic chemistry

The field of heterocyclic chemistry has long presented a special challenge for chemists. Because of the enormous amount and variety of information, it is often a difficult topic to cover for undergraduate and graduate chemistry students, even in simplified form. Yet the chemistry of heterocyclic compounds and methods for their synthesis form the bedrock of modern medicinal chemical and pharmaceutical research. Thus there is a great need for high quality, up-to-date, and authoritative books on heterocyclic synthesis helpful to both the professional research chemist as well as the advanced student.

Name Reactions in Heterocyclic Chemistry provides a one-stop repository for this important field of organic chemistry. The primary topics include three- and four-membered heterocycles, five-membered heterocycles including indoles, furans, thiophenes, and oxazoles, six-membered heterocycles including quinolines, isoquinolines, and pyrimidines, and other heterocycles.

Each name reaction is summarized in seven sections:

  • Description
  • Historical perspective
  • Mechanism
  • Variations and improvements
  • Synthetic utility
  • Experimental
  • References
Authored by a team of world-renowned contributors - some of whom have discovered the very reactions they describe - Name Reactions in Heterocyclic Chemistry represents a state-of-the-art resource for students and researchers alike.
Foreword x
Preface xi
Acronyms and abbreviations xiv
PART 1 THREE-AND FOUR-MEMBERED HETEROCYCLES
1(68)
Epoxides and Aziridines
1(68)
Corey--Chaykovsky reaction
2(13)
Darzens glycidic ester condensation
15(7)
Hoch--Campbell aziridine synthesis
22(7)
Jacobsen--Katsuki epoxidation
29(15)
Paterno--Buchi reaction
44(6)
Sharpless--Katsuki epoxidation
50(13)
Wenker aziridine synthesis
63(6)
PART 2 FIVE-MEMBERED HETEROCYCLES
69(232)
Pyrroles and Pyrrolidines
69(30)
Barton--Zard reaction
70(9)
Knorr and Paal-Knorr pyrrole syntheses
79(11)
Hofmann--Loffler--Freytag reaction
90(9)
Indoles
99(84)
Bartoli indole synthesis
100(4)
Batcho--Leimgruber indole synthesis
104(6)
Bucherer carbazole synthesis
110(6)
Fischer indole synthesis
116(12)
Gassman indole synthesis
128(4)
Graebe--Ullman carbazole synthesis
132(3)
Hegedus indole synthesis
135(5)
Madelung indole synthesis
140(5)
Nenitzescu indole synthesis
145(9)
Reissert indole synthesis
154(6)
Furans
Feist--Benary furan synthesis
160(8)
Paal--Knorr furan synthesis
168(15)
Thiophenes
183(36)
Fiesselmann thiophene synthesis
184(9)
Gewald aminothiophene synthesis
193(6)
Hinsberg synthesis of thiophene derivatives
199(8)
Paal thiophene synthesis
207(12)
Oxazoles and Isoxazoles
219(42)
Claisen isoxazole synthesis
220(5)
Cornforth rearrangement
225(4)
Erlenmeyer--Plochl azlactone synthesis
229(5)
Fischer oxazole synthesis
234(3)
Meyers oxazoline method
237(12)
Robinson--Gabriel synthesis
249(5)
van Leusen oxazole Synthesis
254(7)
Other Five-Membered Heterocycles
261(40)
Auwers flavone synthesis
262(4)
Bucherer--Bergs reaction
266(9)
Cook--Heilbron 5-amino-thiazole synthesis
275(9)
Hurd--Mori 1,2,3-thiadiazole synthesis
284(108)
Knorr pyrazole synthesis
392
PART 3 SIX-MEMBERED HETEROCYCLES
301(244)
Pyridines
302(73)
Preparation via condensation reactions
303(20)
Hantzsch (dihydro)-pyridine synthesis
304(1)
Description
304(1)
Historical perspective
304(1)
Mechanism
305(2)
Variations
307(1)
Guareschi-Thorpe pyridine synthesis
307(1)
Chichibabin (Tschitschibabin) pyridine synthesis
308(1)
Bohlmann--Rahtz pyridine synthesis
309(2)
Krohnke pyridine synthesis
311(2)
Petrenko--Kritschenko piperidone synthesis
313(1)
Improvements or modifications
314(6)
Experimental
320(1)
Three-component coupling
320(1)
Two-component coupling
320(1)
References
321(2)
Preparation via cycloaddition reactions
323(17)
Boger reaction
323(17)
Preparation via rearrangement reactions
340(15)
Boekelheide reaction
340(10)
Ciamician-Dennstedt rearrangement
350(5)
Zincke reaction
355(20)
Quinolines and Isoquinolines
375(120)
Bischler--Napieralski reaction
376(10)
Camps quinoline synthesis
386(4)
Combes quinoline synthesis
390(8)
Conrad--Limpach reaction
398(9)
Doebner quinoline synthesis
407(4)
Friedlander synthesis
411(5)
Gabriel--Colman rearrangement
416(7)
Gould--Jacobs reaction
423(14)
Knorr quinoline synthesis
437(6)
Meth--Cohn quinoline synthesis
443(8)
Pfitzinger quinoline synthesis
451(6)
Pictet--Gams isoquinoline synthesis
457(8)
Pictet--Hubert reaction
465(4)
Pictet--Spengler isoquinoline synthesis
469(11)
Pomeranz--Fritsch reaction
480(7)
Riehm quinoline synthesis
487(1)
Skraup/Doebner--von Miller reaction
488(7)
Other Six--Membered Heterocycles
495(50)
Algar--Flynn--Oyamada reaction
496(8)
Beirut reaction
504(5)
Biginelli reaction
509(12)
Kostanecki--Robinson reaction
521(15)
Pinner pyrimidine synthesis
536(4)
von Richter cinnoline reaction
540(5)
Subject Index 545
JIE JACK LI is a medicinal chemist at Pf izer Global Research and Development in Ann Arbor, Michigan. His research interests include medicinal chemistry, heterocyclic chemistry, transition metal-catalyzed reactions, and radical chemistry. He is author of Name Reactions: A Collection of Detailed Reaction Mechanisms, and coauthor of Palladium in Heterocyclic Chemistry and Contemporary Drug Synthesis, also published by Wiley.
Li has previously written a book on name reactions in organic chemistry that included simple reaction mechanisms and applications for the included reactions. The present book, the first of a planned two-volume set, applies the same formula to name reactions in heterocyclic chemistry, a large and diverse branch of organic chemistry that is especially important in medicinal and pharmaceutical research. Many well-known name reactions, such as the Knorr, Hantsch, and Fischer syntheses, involve heterocyclic species, and have been described previously; however, the tendency of synthetic chemists to self-brand their discoveries is so great that there are plenty of new reactions described here (there is even one named after a city!). This volume describes about 70 reactions, and covers 3, 4, 5, and 6-membered rings. While nitrogen, oxygen and sulfur heterocycles are well covered for the smaller rings, the section on 6-membered heterocycles is almost exclusively devoted to nitrogen-containing rings, and ignores the other heteroatoms. Perhaps the forthcoming volume of the set will fill in these gaps in coverage, and will also include important larger-ring heterocyclic systems such as azepines, diazepines, and oxepines. The treatment of each reaction is usually presented in seven sections: description, historical perspective, mechanism, variations and improvements, synthetic utility, experimental, and references. Of particular value is the experimental section, which presents an illustrative procedure for the reaction, usually from the recent journal literature. While this book cannot and does not intend to be comprehensive (one must turn to Katritzky's multi-volume Comprehensive Heterocyclic Chemistry for that), it is a unique and valuable addition to a relatively underserved branch of chemistry.Recommended for upper level undergraduates through professionals.Reviewer: F. Bartow Culp, Chemistry Librarian, Purdue University M. G. Mellon Library, bculp@purdue.edu Copyright 2006 E-Streams Reviews.

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