Z703125 Sigma

Name Reactions in Heterocyclic Chemistry

this book provides a one-stop repository for this important field of organic chemistry

  •  ISBN-10 0-47130215-5

  •  ISBN-13 978-0-47130215-5

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publication info   J. Li, ed., John Wiley & Sons, 2005, 558 pp., hard cover

Description

General description

The chemistry of heterocyclic compounds and methods for their synthesis form the bedrock of modern medicinal chemical and pharmaceutical research. This book 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; and References.

Table of Contents

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.Buchi 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-Loffler-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.Benary 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 Krohnke 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 Friedlander 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
9.15 Pomeranz.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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