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Paper | Regular issue | Vol 43, No. 4, 1996, pp.817-828
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7366
Metallation of Methoxy-2(1H)-quinolinones

Trinidad Moreno, María Fernández, Elena de la Cuesta, and Carmen Avendaño*

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

Abstract

Methoxy group at 5- or 6-position of 2(1H)-quinolinones is compatible with the regioselective electrophilic substitution and chain enlargement at the 3-position imposed by the ortho-directed effect of the quinolinone lithium salt. The coordination effect of a methoxy group at the 8-position changes the reaction course, precluding the ortho-directed metallation and enhancing the conjugate addition at the 4-position.