SYNTHESIS OF 1-[ARYL(HETEROARYL)]-5-(3,3,3-TRIFLUORO-2-OXO-PROPYLIDENE)PYRROLIDIN-2-ONES / SÍNTESE DE 1-[ARIL(HETEROARIL)]-5-(3,3,3-TRIFLUOR-2-OXOPROPILIDENO) PIRROLIDIN-2-ONAS

AUTOR(ES)

Graciela Aparecida de Oliveira

DATA DE PUBLICAÇÃO

2005

RESUMO

The synthesis of a series of ten 1-[aryl(heteroaryl)]-5-(3,3,3-trifluoro-2-oxopropilideno) pyrrolidin-2-ones by intramolecular cyclocondensation reaction of methyl 7,7,7-trifluoro-4-[aryl(heteroaryl)amino]-6-oxo-4-heptanoates in excellent yields (69-95%) is reported. The methyl heptanoate intermediates were obtained in three sequential steps: (i) acetalization of 4-oxopentanoic acid with trimethyl orthoformate; (ii) acetylation of the acetal with trifluoroacetic anhydride; (iii) reaction of methyl 7,7,7-trifluoro-4-methoxy-6-oxo-4-heptanoate with primary amines [R NH2, where R = PhCH2, PhCH2CH2, Ph, 4-Me-C6H4, 4-MeO-C6H4, 4-Cl-C6H4, 4-Br-C6H4, 4-NH2-C6H4, pyrid-2-yl, isoxazol-2-yl) to obtain methyl 7,7,7-trifluoro-4-[aryl(heteroaryl)amino]-6-oxo-4-heptanoates in moderate to good yields (57 95%).

ASSUNTO(S)

sintese organica quimica organica compostos heterociclicos pirrolidinonas quimica quimica

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