Studies in SRN1 series. Part 14. Direct synthesis of benzo [c] phenanthridines and benzo [c] phenanthridones via SRN1 reactions

…, H Ginsburg, L Quintero-Cortes, G Roussi

Index: Beugelmans, Rene; Chastanet, Jacqueline; Ginsburg, Helene; Quintero-Cortes, Leticia; Roussi, Georges Journal of Organic Chemistry, 1985 , vol. 50, # 24 p. 4933 - 4938

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Citation Number: 62

Abstract

A straightforward and high-yield route to the 11, 12-dihydrobenzo [c] phenanthridine (3) and 11, 12-dihydrobenzo [c] phenanthridone (14) ring systems is based upon an SRN~ reaction between 2-halobenzylamines 1 or 2-halobenzoic acids 11 and enolates derived from tetralones 2. The efficient dehydrogenation of 3 or 14 gives the benzo [clphenanthridines 4 or benzo [c] phenanthridones 15. Use of properly substituted reactants leads to nitidine, ...