Published in
Sociedade Brasileira de Química, SBQ, Journal of the Brazilian Chemical Society, 1(19), p. 184-193, 2008
DOI: 10.1590/s0103-50532008000100026
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Efficient synthesis of new 1-[Alkyl(aryl)]-5-(3,3,3-trihalo-2-oxopropylidene)pyrrolidin-2-ones
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Flores,Darlene C.,
Darlene C. Flores ,
Rubia M. S. da Silva,
Graciela Oliveira,
Oliveira,Graciela,
Lucas Pizzuti,
Silva,Rubia M. S. Da,
R. Da Silva,
Marcos A. P. Martins ,
Martins,Marcos A. P.,
Helio G. Bonacorso,
Bonacorso,Helio G.
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Abstract
Reactions of methyl 4-methoxy-6-oxo-7,7,7-trihalo-4-heptenoates 1 and 2 with primary amines RNH2, where R = PhCH2, PhCH2CH2, Ph, 4-MeC6H4, 4-MeOC6H4, 4-ClC6H4, 4-BrC6H4, 2-pyridyl, 5-methyl-3-isoxazolyl, 4-NH2C6H4 affording methyl 4-[alkyl(aryl)amino]-6-oxo-7,7,7-trihalo-4-heptenoates 3, 4, in good yields (57-95%), which suffer quantitative intramolecular cyclocondensation to produce 1-alkyl(aryl)-5-(2-oxo-3,3,3-trihalopropylidene)pyrrolidin-2-ones 5, 6, are reported. The structures of the isolated new products were assigned by means of ¹H,13C NMR measurements and mass spectrometry. The Z and E configuration of compounds 3d and 5b respectively were established from X-ray crystallography.