Abstract
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.
Original language | English |
---|---|
Pages (from-to) | 987-996 |
Number of pages | 10 |
Journal | Chemical and Pharmaceutical Bulletin |
Volume | 61 |
Issue number | 10 |
DOIs | |
Publication status | Published - 2013 Oct |
Keywords
- C-H functionalization
- Cyclization
- Heterocyclic compound
- Palladium
ASJC Scopus subject areas
- Chemistry(all)
- Drug Discovery