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

Synthetic studies on 5-(3,4-dimethoxyphenyl)-5,6-dihydrophenanthridin-6-ol,an analogue of perloline

SI Clarke and RH Prager

Australian Journal of Chemistry 35(8) 1645 - 1653
Published: 1982

Abstract

Two independent syntheses of the title compound (2), an analogue of perloline, are described. 9-(3,4-Dimethoxyphenyl)fluoren-9-ol reacted with hydrazoic acid in polyphosphoric acid to give 6-(3,4-dimethoxyphenyl)phenanthridine, the N-oxide of which was photolysed to 5-(3,4-dimethoxy-phenyl)phenanthridin-6-one (8) which was reduced to the title compound directly with sodium bis(2-methoxyethoxy)aluminium hydride ('Redal'), or by reduction to 5-(3,4-dimethoxypheny1)-5,6- dihydrophenanthridine followed by oxidation with N-bromosuccinimide. The phenanthridinone (8) was also synthesized by photolysis of the nitrone of 3,4-dimethoxy-N-fluorenylideneaniline.

https://doi.org/10.1071/CH9821645

© CSIRO 1982

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