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Short Paper | Regular issue | Vol 89, No. 3, 2014, pp.739-746
Published online, 29th January, 2014
DOI: 10.3987/COM-13-12919
■ Synthesis of 10-Substituted Benzo[b][1,8]naphthyridin-5(10H)-ones Based on the Reaction of (2-Chloropyridin-3-yl)(2-halophenyl)methanones with Primary Amines

Kazuhiro Kobayashi,* Shohei Yuba, and Toshihide Komatsu

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

Abstract

The reaction of (2-chloropyridin-3-yl)(2-halophenyl)methanones, derived from 2-chloropyridine and 2-halobenzaldehydes, with two equivalents of benzenamines or arylmethanamines followed by treatment of the resulting (2-aryl(or arylmethyl)aminopyridin-2-yl)(2-halophenyl)methanones with sodium hydride in DMF at 0 ˚C to room temperature have proven to provide an efficient method for the preparation of 10-aryl(or arylmethyl)benzo[b][1,8]naphthyridin-5(10H)-ones. This methodology is shown to be applicable for the preparation benzo[b][1,7]naphthyridin-5(10H)-one derivatives by using 3-chloropyridine as a starting material in place of 2-chloropyridine.