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

doi:10.15826/chimtech.2015.2.2.010

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

This work is licensed under a Creative Commons Attribution 4.0 International License.

Chimica Techno Acta, 2014–2025
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