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

A. A. Poluikova, A. Yu. Platonova, T. V. Glukhareva, Yu. Yu. Morzherin

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.

Keywords


tert-amino effect; quinoline; cyclization; thioamide

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References


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DOI: https://doi.org/10.15826/chimtech.2015.2.2.010

Copyright (c) 2015 A. A. Poluikova, A. Yu. Platonova, T. V. Glukhareva, Yu. Yu. Morzherin

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Chimica Techno Acta, 2014-2022
ISSN 2411-1414 (Online)