Incorporation of the quinoline-5, 8-quinone moiety into polyaza cavities

RP Thummel, S Chirayil, C Hery, JL Lim…

Index: Thummel, Randolph P.; Chirayil, Sara; Hery, Christophe; Lim, Jean-Luc; Wang, Tie-Lin Journal of Organic Chemistry, 1993 , vol. 58, # 7 p. 1666 - 1671

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Citation Number: 22

Abstract

Silica gel supported nitric acid treatment of 2, 5-dimethoxybenzaldehyde followed by reduction with iron powder provides 3, 6-dimethoxy-2-aminobenzaldehyde. Friedlinder condensation of this species with a variety of ketones and diketones leads to 5, &dimethoxyquinoline derivatives which may be oxidized by ceric ammonium nitrate (CAN) and pyridine-2, 6-dicarboxylic acid N-oxide (PDANO) to the corresponding quinones. The ...