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Paper | Regular issue | Vol 78, No. 12, 2009, pp.2993-3000
Published online, 15th September, 2009
DOI: 10.3987/COM-09-11810
One-Pot Synthesis of Three Types of 2,3-Disubstituted Thienopyridines from Halopyridinyl Ketones

Kazuhiro Kobayashi,* Taketoshi Kozuki, and Hisatoshi Konishi

*Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

This report describes a one-pot synthesis of three types of thienopyridine derivatives from the respective halopyridinyl ketones. Thus, the reaction of 2-bromopyridin-3-yl ketones, derived from 2-bromopyridine, with sodium sulfide followed by successive treatment BrCH2EWG’s and sodium hydride afforded 2,3-disubstituted thieno[2,3-b]pyridines. Similar one-pot sequences starting from aryl 3-bromopyridin-4-yl ketones and aryl 4-chloropyridin-3-yl ketones could also be readily performed to afford 2,3-disubstituted thieno[2,3-c]pyridines and 2,3-disubstituted thieno[3,2-c]pyridines, respectively.