A 'biogenetic like' synthesis of perloline, 6-(3,4-Dimethoxyphenyl)-5-hydroxy-5,6-dihydrobenzo[c][2,7]naphthyridin-4(3H)-one
- 1 January 1983
- journal article
- research article
- Published by CSIRO Publishing in Australian Journal of Chemistry
- Vol. 36 (7) , 1431-1440
- https://doi.org/10.1071/ch9831431
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.Keywords
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