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Paper | Regular issue | Vol 34, No. 9, 1992, pp.1749-1758
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6070
General Synthesis of 2,3-Substituted 5-Membered Heterocyclic Quinones

Mahmoud Cherif, Philippe Cotelle,* and Jean-Pierre Catteau

*Laboratoire de Chimie Organique Physique, URA CNRS 351, U. S. T. Lille, Villeneuve d’ Ascq, France

Abstract

4,7-Dimethoxybenzo[b]furan, -thiophene, -selenophene and 4,7-dimethoxyindole have been prepared by a two-step procedure involving a cyclization-dehydration of the acetals (1). The oxidative demethylation of 4,7-dimethoxybenzo[b]thiophene, -selenophene and 4,7-dimethoxyindole afforded the corresponding quinones whereas 4,7-dimethoxybenzo[b]furan gave 5,5’-bisbenzo[b]furan-1,4-dionyl (4b).