%0 Journal Article
%T Efficient synthesis of new 1-[Alkyl(aryl)]-5-(3,3,3-trihalo-2-oxopropylidene)pyrrolidin-2-ones
%A Flores
%A Alex F. C.
%A Flores
%A Darlene C.
%A Oliveira
%A Graciela
%A Pizzuti
%A Lucas
%A Silva
%A Rubia M. S. da
%A Martins
%A Marcos A. P.
%A Bonacorso
%A Helio G.
%J Journal of the Brazilian Chemical Society
%D 2008
%I Sociedade Brasileira de Qu¨Şmica, SBQ
%R 10.1590/S0103-50532008000100026
%X 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.
%K pyrrolidin-2-ones
%K [cccc+n] cyclisation
%K methyl 4-methoxy-6-oxo-7
%K 7
%K 7-trihalo-4-heptenoates.
%U http://www.scielo.br/scielo.php?script=sci_abstract&pid=S0103-50532008000100026&lng=en&nrm=iso&tlng=en