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Short Paper | Regular issue | Vol 89, No. 7, 2014, pp.1687-1695
Published online, 3rd June, 2014
DOI: 10.3987/COM-14-13016
Synthesis of N,N-Dialkyl-5(or 10)-oxobenzo[b][1,8 or 1,7(or 1,6)]naphthyridine-10(5H)(or 5(10H))-carbothioamides Based on the Reaction of the Respective (Chloropyridinyl)(2-isothiocyanatophenyl)methanones with Secondary Amines

Kazuhiro Kobayashi,* Kazuhiro Nakagawa, and Hiroki Inouchi

*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 addition of secondary amines to (2-chloropyridin-3-yl)(2-isothiocyanatophenyl)methanone, derived from 2-chloropyridine and N-(2-formylphenyl)formamide, followed by treatment of the resulting thiourea intermediates with sodium hydride has proven to provide a method for the synthesis of N,N-dialkyl-5-oxobenzo[b][1,8]naphthyridine-10(5H)- carbothioamides. Similarly, N,N-dialkyl-5-oxobenzo[b][1,7]naphthyridine-10(5H)-carbothioamides and N,N-dialkyl-10-oxobenzo[b][1,6]naphthyridine-5(10H)-carbothioamides can be prepared from the respective (chloropyridinyl)(2-isothiocyanatophenyl)methanones.