A facile synthesis of ethyl α-cyano-β-amincacrylates and related compounds

Harjit Singh, ; Gandhi, Chander S. (1978) A facile synthesis of ethyl α-cyano-β-amincacrylates and related compounds Synthetic Communications, 8 (7). pp. 469-472. ISSN 0039-7911

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Related URL: http://dx.doi.org/10.1080/00397917808063574

Abstract

Ethyl-α-cyano-β-aminoacrylates (I) have been used as intermediates in the synthesis of pyrimidine derivatives and I(R=H,CH3, C6H5) have been obtained by the condensations of ethyl cyanoacetate with amidines and iminoethers, in relatively poor yields. We now report that both biprotic and monoprotic carbothioamides-thioformamide, thiobenzamides, phenylthioacetamide, quinazolin-4(3H)-thione and pyrrolidin-2(1H)-thione condense with ethyl bromocyanoacetate, with extrusion of sulphur, to form ethyl α-cyano-β-aminoacrylate (I, R=H), ethyl α-cyano-β-aminocinnamates (I, R=-C6H5,-C6H4-OCH3, -C6H4-NO2,P), ethyl α-cyano-β-amino-β-benzylacrylate (I, R= -CH2C6H5), ethyl-α-cyano Δ4(3H), quinazolineace tate (II) and ethyl α-cyano-Δ2,α, pyrrolidineacetate (III) (Table) respectively.

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