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A Facile Synthesis of Ethyl α-Cyano-β-amincacrylates and Related Compounds

 

作者: Harjit Singh,   ChanderS. Gandhi,  

 

期刊: Synthetic Communications  (Taylor Available online 1978)
卷期: Volume 8, issue 7  

页码: 469-472

 

ISSN:0039-7911

 

年代: 1978

 

DOI:10.1080/00397917808063574

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

Ethyl-α-cyano-β-aminoacrylates (I) have been used as intermediates in the synthesis of pyrimidine derivatives1,2and I(R=H,CH3, C6H5) have been obtained by the condensations of ethyl cyanoacetate with amidines and iminoethers, in relatively poor yields.2We 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,αpyrrolidineacetate (III) (Table) respectively.

 

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