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Title:
Name reactions in heterocyclic chemistry
Publication Information:
Hoboken, N.J. : Wiley-Interscience, 2005.
ISBN:
9780471302155
Added Author:

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30000010080502 QD400 N34 2005 Open Access Book Book
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30000010081819 QD 400 N34 2005 Open Access Book Book
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Summary

Summary

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.


Author Notes

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.


Table of Contents

Foreword
Preface
Acronyms and abbreviations
Part 1 Three- and Four-Membered Heterocycles
Chapter 1 Epoxides and Aziridines
1.1 Corey
Chaykovsky reaction
1.2 Darzens glycidic ester condensation
1.3 Hoch
Campbell aziridine synthesis
1.4 Jacobsen
Katsuki epoxidation
1.5 Paterno
Bchi reaction
1.6 Sharpless-Katsuki epoxidation
1.7 Wenker aziridine synthesis
Part 2 Five-Membered Heterocycles
Chapter 2 Pyrroles and Pyrrolidines
2.1 Barton
Zard reaction
2.2 Knorr and Paal-Knorr pyrrole syntheses
2.3 Hofmann
L"ffler
Freytag reaction
Chapter 3 Indoles
3.1 Bartoli indole synthesis
3.2 Batcho
Leimgruber indole synthesis
3.3 Bucherer carbazole synthesis
3.4 Fischer indole synthesis
3.5 Gassman indole synthesis
3.6 Graebe
Ullman carbazole synthesis
3.7 Hegedus indole synthesis
3.8 Madelung indole synthesis
3.9 Nenitzescu indole synthesis
3.10 Reissert indole synthesis
Chapter 4 Furans
4.1 Feist
Bnary furan synthesis
4.2 Paal
Knorr furan synthesis
Chapter 5 Thiophenes
5.1 Fiesselmann thiophene synthesis
5.2 Gewald aminothiophene synthesis
5.3 Hinsberg synthesis of thiophene derivatives
5.4 Paal thiophene synthesis
Chapter 6 Oxazoles and Isoxazoles
6.1 Claisen isoxazole synthesis
6.2 Cornforth rearrangement
6.3 Erlenmeyer azlactone synthesis
6.4 Fischer oxazole synthesis
6.5 Meyers oxazoline method
6.6 Robinson
Gabriel synthesis
6.7 van Leusen Oxazole Synthesis
Chapter 7 Other Five-Membered Heterocycles
7.1 Auwers flavone synthesis
7.2 Bucherer
Bergs reaction
7.3 Cook
Heilbron 5-amino-thiazole synthesis
7.4 Hurd
Mori 1,2,3-thiadiazole synthesis
7.5 Knorr pyrazole synthesis
Part 3 SIX-MEMBERED HETEROCYCLES
Chapter 8 Pyridines
8.1 Preparation via condensation reactions
8.1.1 Hantzsch (Dihydro)-pyridine synthesis
8.1.1.1 Description
8.1.1.2 Historical perspective
8.1.1.3 Mechanism
8.1.1.4 Variations
8.1.1.4.1 Guareschi-Thorpe pyridine synthesis
8.1.1.4.2 Chichibabin (Tschitschibabin) pyridine synthesis
8.1.1.4.3 Bohlmann
Rahtz pyridine synthesis
8.1.1.4.4 Kr"hnke pyridine synthesis
8.1.1.4.5 Petrenko
Kritschenko piperidone synthesis
8.1.1.5 Improvements or modifications
8.1.1.6 Experimental
8.1.1.6.1 Three-component coupling
8.1.1.6.2 Two-component coupling
8.1.1.7 References
8.2 Preparation via cycloaddition reactions
8.2.1 Boger reaction
8.3 Preparation via rearrangement reactions
8.3.1 Boekelheide reaction
8.3.2 Ciamician-Dennstedt rearrangement
8.4 Zincke reaction
Chapter 9 Quinolines and Isoquinolines
9.1 Bischler
Napieralski reaction
9.2 Camps quinoline synthesis
9.3 Combes quinoline synthesis
9.4 Conrad
Limpach reaction
9.5 Doebner quinoline synthesis
9.6 Friedlnder synthesis
9.7 Gabriel
Colman rearrangement
9.8 Gould
Jacobs reaction
9.9 Knorr quinoline synthesis
9.10 Meth
Cohn quinoline synthesis
9.11 Pfitzinger quinoline synthesis
9.12 Pictet
Gams isoquinoline synthesis
9.13 Pictet
Hubert reaction
9.14 Pictet
Spengler isoquinoline synthesis
9.15vPomeranz Fritsch reaction
9.16 Riehm quinoline synthesis
9.17 Skraup Doebner
von Miller reaction
Chapter 10 Other Six.Membered Heterocycles
10.1 Algar
Flynn
Oyamada reaction
10.2 Beirut reaction
10.3 Biginelli reaction
10.4 Kostanecki
Robinson reaction
10.5 Pinner pyrimidine synthesis
10.6 von Richter cinnoline reaction
Subject Index
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