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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

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 and ST Were

Australian Journal of Chemistry 36(7) 1431 - 1440
Published: 1983

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.

https://doi.org/10.1071/CH9831431

© CSIRO 1983

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