Synthesis of 3,13-dichlorobenzo[b]quino[4,3-h][1,6]naphthyridin-6(5H)-one derivatives from 2-oxoquinoline-3-carbonyl chloride and 2,6-dichloroquinolin-4-amine

Abstract

The reaction of 2-oxo-1,2-dihydroquinoline-3-carbonyl chlorides and 2,6-dichloroquinolin-4-amine leads to the formation of N-(2,6-dichloroquinolin-4-yl)-2-oxo-1,2-dihydroquinoline-3-carboxamides. The latter is cyclized to fused [1,6]naphthyridine derivative – 3,13-dichlorobenzo[b]quino[4,3-h][1,6]naphthyridin-6(5H)-one, under heating in polyphosphoric acid at 150°C. The reaction sequence was generalized and was extended to synthetic derivatives. The structures of all synthesized compounds were confirmed by spectral data and elemental analysis.