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Short Paper | Regular issue | Vol 91, No. 7, 2015, pp.1439-1444
Published online, 2nd June, 2015
DOI: 10.3987/COM-15-13233
Synthesis of 10-Substituted Pyrido[2,3-b][1,8]naphthyridin-5(10H)-ones (Anthyridin-5(10H)-ones) Based on the Reaction of Bis(2-chloropyridin-3-yl)methanones with Primary Amines

Kazuhiro Kobayashi,* Toshihide Komatsu, Shohei Yuba, Yuuki Chikazawa, and Miyuki Tanmatsu

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


An efficient method for the preparation of 10-substituted pyrido[2,3-b][1,8]naphthyridin-5(10H)-ones, utilizing the reaction of bis(2-chloropyridin-3-yl)methanone, derived from 2-chloropyridine and 2-chloropyridine-3-carbaldehyde, with primary amines under heating at 80 ˚C, followed by sodium hydride promoted intramolecular ring closure of the resulting (2-aminopyridin-3-yl)(2-halopyridin-3-yl)methanone derivatives, has been developed. A similar sequence starting with (2-chloropyridin-3-yl)(3-chloropyridin-4-yl)methanone, derived from 3-chloropyridine and 2-chloropyridine-3-carbaldehyde, leads to the formation of 10-substituted pyrido[2,3-b][1,7]naphthyridin-5(10H)-ones.