Synthesis of 5-thiocarbomoyl- and 5-(thiazol-2-yl)-2,3,4,4a,5,6-hexahydro-1Н-pyrido[1,2-a]quinoline-5-carbonitriles

Abstract

The tert-amino effect cyclizations are an efficient and convenient route to synthetically as well as biologically important ring-fused tetrahydroquinolines. The method is operationally simple and highly diastereoselective. Herein we representour studies of the tert-amino effect reaction ortho-dialkylaminobenzaldehydes and cyanthioacetamide or [4-aryl-1,3-thiazol-2yl]acetonitrile.It was found 9-chloro-5-(4-phenylthiazol-2-yl)-2,3,4,4a,5,6-hexahydro-1Н-pyrido[1,2-a]quinoline-5-carbinitrile can easily be obtained from 9-chloro-5-cyano-2,3,4,4а,5,6-hexahydro-1H-pyrido[1,2-a] quinoline-5-carbothioamide andα-bromoacetophenone condensation.