Reaction of Isatin-1-acetamides with Alkoxides: Synthesis of Novel 1,4-Dihydro-3-hydroxy-4-oxo-2-quinolinecarboxamides

María Mercedes Blanco; Mónica Dal Maso; María Sol Shmidt; Isabel Amalia Perillo

doi:10.1055/s-2007-965949

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Reaction of Isatin-1-acetamides with Alkoxides: Synthesis of Novel 1,4-Dihydro-3-hydroxy-4-oxo-2-quinolinecarboxamides

María Mercedes Blanco, Mónica Dal Maso, María Sol Shmidt, Isabel Amalia Perillo*
Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Junín 956, 1113 Buenos Aires, Argentina
Fax: +54(11)49648250; e-Mail: iperillo@ffyb.uba.ar;

Abstract

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Abstract

The study of the reactivity of a series of isatin-1-acetamides with hot alkoxides is described. These reactions lead to 1,4-dihydro-3-hydroxy-4-oxo-2-quinolinecarboxamides as main products, and 3-hydroxy-2-oxindoles as well as other minor products. Experimental results indicate that the starting compounds undergo transformation through two principal routes: ring expansion of isatin leading to quinoline carboxamides, probably as the result of a ring-opening and ring-closure rearrangement, and reduction of the keto carbonyl group due to the reductive ability of alkoxides.

Key words

4-quinolinones - isatin - alkylation - rearrangement - reduction

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References

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