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Amide and thioamide of cyanoacetic acid in АdNE type reactions with 2-halopyridinium salts

A mixture of pyridine-2-thiones and 2-amino-1-cyanoindolizines was obtained by condensation of N -[(alkoxycarbonyl)methyl]- or N -[(aroyl)-methyl]-2-chloro(bromo)pyridinium halides in the presence of 2 equivalents of triethylamine. Furthermore, reacting cyanoacetamide with N -[(alkoxycarbonyl)methyl...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2015-03, Vol.51 (1), p.56-59
Main Authors: Tverdokhleb, Natalya M., Khoroshilov, Gennadii E.
Format: Article
Language:English
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Summary:A mixture of pyridine-2-thiones and 2-amino-1-cyanoindolizines was obtained by condensation of N -[(alkoxycarbonyl)methyl]- or N -[(aroyl)-methyl]-2-chloro(bromo)pyridinium halides in the presence of 2 equivalents of triethylamine. Furthermore, reacting cyanoacetamide with N -[(alkoxycarbonyl)methyl]-2-chloro(bromo)pyridinium salts afforded a mixture of 2-amino-1-carbamoylindolizine-3-carboxylates and a novel heterocyclic system, 2,4-dioxo-2,3,4,5-tetrahydropyrido[1,2- d ][1,4]diazepine-1-carbonitrile.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-015-1659-8