Australian journal of chemistry

A'biogenetic like'synthesis of perloline, 6-(3, 4-Dimethoxyphenyl)-5-hydroxy-5, 6-dihydrobenzo [c][2, 7] naphthyridin-4 (3H)-one

T Duong, RH Prager, ST Were

Index: Duong, Thach; Prager, Rolf H.; Were, Stephen T. Australian Journal of Chemistry, 1983 , vol. 36, # 7 p. 1431 - 1440

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Citation Number: 6

Abstract

Abstract 9H-Indeno [2, 1-c] pyridine-1 (2H), 9-dione, prepared by a new efficient route, reacts with 3, 4-dimethoxy-phenyllithium to form the keto alcohol (7), which rearranges with hydrazoic acid to form 5-(3, 4-dimethoxyphenyl) benz [c][2, 7] naphthyridin-4 (3H)-one. The N-oxide photolyses smoothly to yield dehydroperloline as the sole product.