Este trabalho mostra a síntese, em bons rendimentos (57-95%), de duas séries de 1-alquil(aril) amino-2-oxo-5-(2-oxo-3,3,3-trialopropiliden)-pirrolidinas 5 e 6, a partir dos intermediários 4-[alquil(aril)amino]-6-oxo-7,7,7-trialo-4-hepteno-atos de metila 3 e 4 obtidos por substituição da metoxila-nos precursores 4-metoxi-6-oxo-7,7,7-trialo-4-heptenoatos de metila 1 e 2, pela série de aminas primárias RNH 2 , onde R = PhCH 2 , PhCH 2 CH 2 , Ph, 4-MeC 6 H 4 , 4-MeOC 6 H 4 , 4-ClC 6 H 4 , 4-BrC 6 H 4 , 2-piridnil, 5-metil-3-isoxazolil, 4-NH 2 C 6 H 4 . A estrutura molecular dos produtos inéditos foi atribuída a partir dos dados de RMN 1 H, 13 C e espectrometria de massas. A configuração geométrica dos compostos 3d e 5b foi confirmada pelos dados de difração de raios-X em monocristal.Reactions of methyl 4-methoxy-6-oxo-7,7,7-trihalo-4-heptenoates 1 and 2 with primary amines RNH 2 , where R = PhCH 2 , PhCH 2 CH 2 , Ph, 4-MeC 6 H 4 , 4-MeOC 6 H 4 , 4-ClC 6 H 4 , 4-BrC 6 H 4 , 2-pyridyl, 5-methyl-3-isoxazolyl, 4-NH 2 C 6 H 4 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 1 H, 13 C NMR measurements and mass spectrometry. The Z and E configuration of compounds 3d and 5b respectively were established from X-ray crystallography.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
hi@scite.ai
10624 S. Eastern Ave., Ste. A-614
Henderson, NV 89052, USA
Copyright © 2024 scite LLC. All rights reserved.
Made with 💙 for researchers
Part of the Research Solutions Family.