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Synthesis 1998; 1998(2): 186-194
DOI: 10.1055/s-1998-2014
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A General Synthesis of Quinoline-2,5,8(1H)-triones via Acylation of 2,5-Dimethoxyaniline with S-tert-Butyl Thioacetates by Application of the Knorr Cyclization

Pilar López-Alvarado* , Carmen Avendaño, J. Carlos Menéndez
  • *Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, ES-28040 Madrid, Spain; Fax + 34(91)3 94 18 22; E-mail: josecm@eucmax.sim.ucm.es
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Publication Date:
31 December 2000 (online)

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An efficient synthesis of quinoline-2,5,8(1H)-triones bearing alkyl groups at C3 and/or C4 is described. The reaction sequence employed involves Knorr cyclization of 2,5-dimethoxyanilides into 5,8-dimethoxyquinoline systems, followed by oxidative demethylation with cerium ammonium nitrate. The starting 2,5-dimethoxyanilides were prepared by chemoselective acylation by regioselective alkylation of S-tert-butyl acetothioacetate (1) at C2 and/or C4. The introduction of electrophiles other than alkyl groups at C2 on 1 was also studied.

quinoline-2,5,8(1H)-triones - Knorr cyclization - 2,5-dimethoxyanilides - β-oxo thioesters - regioselective alkylation

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