Name Reactions in Heterocyclic Chemistry

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 xPreface xiAcronyms and abbreviations xivPart 1 Three- And Four-Membered Heterocycles 1Chapter 1 Epoxides and Aziridines 11.1 Corey-Chaykovsky reaction 21.2 Darzens glycidic ester condensation 151.3 Hoch-Campbell aziridine synthesis 221.4 Jacobsen-Katsuki epoxidation 291.5 Paterno-Büchi reaction 441.6 Sharpless-Katsuki epoxidation 501.7 Wenker aziridine synthesis 63Part 2 Five-Membered Heterocycles 69Chapter 2 Pyrroles and Pyrrolidines 692.1 Barton-Zard reaction 702.2 Knorr and Paal-Knorr pyrrole syntheses 792.3 Hofmann-Löffler-Freytag reaguo 90Chapter 3 Indoles 993.1 Bartoli indole synthesis 1003.2 Batcho-Leimgruber indole synthesis 1043.3 Bucherer carbazole synthesis 1103.4 Fischer indole synthesis 1163.5 Gassman indole synthesis 1283.6 Graebe-Ullman carbazole synthesis 1323.7 Hegedus indole synthesis 1353.8 Madelung indole synthesis 1403.9 Nenitzescu indole synthesis 1453.10 Reissert indole synthesis 154Chapter 4 Furans4.1 Feist-Bénary furan synthesis 1604.2 Paal-Knorr furan synthesis 168Chapter 5 Thiophenes 1835.1 Fiesselmann thiophene synthesis 1845.2 Gewald aminothiophene synthesis 1935.3 Hinsberg synthesis of thiophene derivatives 1995.4 Paal thiophene synthesis 207Chapter 6 Oxazoles and Isoxazoles 2196.1 Claisen isoxazole synthesis 2206.2 Cornforth rearrangement 2256.3 Erlenmeyer-Plöchl azlactone synthesis 2296.4 Fischer oxazole synthesis 2346.5 Meyers oxazoline method 2376.6 Robinson-Gabriel synthesis 2496.7 van Leusen oxazole Synthesis 254Chapter 7 Other Five-Membered Heterocycles 2617.1 Auwers flavone synthesis 2627.2 Bucherer-Bergs reaction 2667.3 Cook-Heilbron 5-amino-thiazole synthesis 2757.4 Hurd-Mori 1,2,3-thiadiazole synthesis 2847.5 Knorr pyrazole synthesis 392Part 3 Six-Membered Heterocycles 301Chapter 8 Pyridines 3028.1 Preparation via condensation reactions 3038.1.1 Hantzsch (dihydro)-pyridine synthesis 3048.1.1.1 Description 3048.1.1.2 Historical perspective 3048.1.1.3 Mechanism 3058.1.1.4 Variations 3078.1.1.4.1 Guareschi-Thorpe pyridine synthesis 3078.1.1.4.2 Chichibabin (Tschitschibabin) pyridine synthesis 3088.1.1.4.3 Bohlmann-Rahtz pyridine synthesis 3098.1.1.4.4 Kröhnke pyridine synthesis 3118.1.1.4.5 Petrenko-Kritschenko piperidone synthesis 3138.1.1.5 Improvement or modifications 3148.1.1.6 Experimental 3208.1.1.6.1 Three-component coupling 3208.1.1.6.2 Two-component coupling 3208.1.1.7 References 3218.2 Preparation via cycloaddition reactions 3238.2.1 Boger reaction 3238.3 Preparation via rearrangement reactions 3408.3.1 Boekelheide reaction 3408.3.2 Ciamician-Dennstedt rearrangement 3508.4 Zincke reaction 355Chapter 9 Quinolines and Isoquinolines 3759.1 Bischler-Napieralski reaction 3769.2 Camps quinoline synthesis 3869.3 Combes quinoline synthesis 3909.4 Conrad-Limpach reaction 3989.5 Doebner quinoline synthesis 4079.6 Friedländer synthesis 4119.7 Gabriel-Colman rearrangement 4169.8 Gould-Jacobs reaction 4239.9 Knorr quinoline synthesis 4379.10 Meth-Cohn quinoline synthesis 4439.11 Pfitzinger quinoline synthesis 4519.12 Pictet-Gams isoquinoline synthesis 4579.13 Pictet-Hubert reaction 4659.14 Pictet-Spengler isoquinoline synthesis 4699.15 Pomeranz-Fritsch reaction 4809.16 Riehm quinoline synthesis 4879.17 Skraup/Doebner-von Miller reaction 488Chapter 10 Other Six-Membered Heterocycles10.1 Algar-Flynn-Oyamada reaction 49610.2 Beirut reaction 50410.3 Biginelli reaction 50910.4 Kostanecki-Robinson reaction 52110.5 Pinner pyrimidine synthesis 53610.6 von Richter cinnoline reaction 540Subject Index 545

"...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)