Synthesis and reactivity of new trifluoromethylated azacyanines starting from 3-(1-amino-2,2,2-trifluororoethylidene)pyrrolidin-2-ones

Bouillon, JP.;Janousek, Z.;Viehe, HG.
(1996) Societe Chimique de France. Bulletin — Vol. 133, n° 5, p. 501-508 (1996)

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  • Bouillon, JP.
    Author
  • Janousek, Z.
    Author
  • Viehe, HG.
    Author
Abstract
The trifluoromethylated enamines 4 and 5 obtained from 3-trifluoroacetyl-pyrrolidinone 1 and ammonia or methylamine, are good precursors for the synthesis of new 4-azapentamethine cyanines 8-10. These 1,5-bis-electrophiles condense with ammonia or phenylhydrazine to give 5H-pyrrolo[2,3-d] pyrimidines 18, 19, pyrimidinone 20 and pyrrolo-[3,2-f]-1,2,4-triazepines 21, 22. The structure and configuration of all the heterocycles are confirmed by their NMR and UV/vis data and by comparison with analogous compounds.
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Bouillon, JP., Janousek, Z., & Viehe, HG. (1996). Synthesis and reactivity of new trifluoromethylated azacyanines starting from 3-(1-amino-2,2,2-trifluororoethylidene)pyrrolidin-2-ones. Societe Chimique de France. Bulletin, 133(5), 501-508. https://hdl.handle.net/2078.5/143898 (Original work published 1996)