著者

Kiyofumi Inamoto

出版者

公益社団法人日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.61, no.10, pp.987-996, 2013-10-01 (Released:2013-10-01)

参考文献数

70

被引用文献数

5 17

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Herein, we describe our development of synthetic methods for heterocyclic compounds based on the palladium-catalyzed carbon–hydrogen bond (C–H) functionalization/intramolecular carbon–heteroatom (nitrogen or sulfur) bond formation process. By this C–H cyclization method, we efficiently prepared various N-heterocycles, including indazoles, indoles, and 2-quinolinones, as well as S-heterocycles such as benzothiazoles and benzo[b]thiophenes. Yields are typically good to high and good functional-group tolerance is observed for each process, thereby indicating that the method provides a novel, highly applicable synthetic route to the abovementioned biologically important heterocyclic frameworks. As an application of this approach, an auto-tandem-type, one-pot process involving the oxidative Heck reaction and subsequent C–H cyclization using cinnamamides and arylboronic acids as starting materials in the presence of a palladium catalyst was also developed for the rapid construction of the 2-quinolinone nucleus.