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

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.