Name Reactions in Heterocyclic Chemistry (eBook)

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.

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.B,nary 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 Friedl"nder 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.

"...is not only an indispensable resource for senior undergraduate
and graduate students....but also a good reference for all chemists
interested in the chemistry of heterocyclic compounds..."
(Drug Development and Industrial Pharmacy, No. 10, 2005)

"...a major contribution to the field and is highly
recommended." (Journal of Medicinal Chemistry, June 30,
2005)