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Paper | Regular issue | Vol 36, No. 10, 1993, pp.2315-2325
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6449
Synthesis of 2,5,8(1H)-Quinolinetrione Derivatives through Vilsmeier-Haack Formylatioin of 2,5-Dimethoxyanilides

Miguel Angel Alonso, Ma del Mar Blanco, Carmen Avendaño,* and J. Carlos Menéndez

*Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense de Madrid, Ciudad Universitaria, 28040 Madrid, Spain

Abstract

The preparation of 2,5,8(1H)-quinolinetrione derivatives bearing both electron-withdrawing and electron-releasing groups at C3 is described. The reaction sequence employed involves Vilsmeier-Haack cyclization of 2,5-dimethoxyanilides into 3-substituted 5,8-dimethoxy-2-chloroquinolines, followed by hydrolysis to the corresponding 2(1H)-quinolinones and oxidative demethylation with cerium ammonium nitrate.