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Paper | Regular issue | Vol 27, No. 7, 1988, pp.1671-1678
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4543
1-Functionalized 5,6-Dimethyl-6H-pyrido[4,3-b]carbazoles (Ellipticines) and Analogues: A New Rapid Synthesis

Emile Bisagni,* Marilys Rautureau, and Christiane Huel

*URA 1387 CNRS, Section de Biologie Batiments 110-112, Institut Curie, 15 Rue Georges Clemenceau 91405 Orsay, France

Abstract

4-Acetyl-2-chloro-3-lithlopyridine ethylene glycol ketal reacts with 3- formyl-5-methoxy-1-methylindole and 3-formyl-1-methyl-1H-pyrrol[3,2-c] pyridine, giving the expected alcohols whose triethylsilane-trifluoroacetic acid reduction at room temperature followed by ketal hydrolysis and cyclisation in acidic medium leads in one step to 1-chloro-9-methoxy-5,6-dimethyl-6H-pyrido[4,3-b] carbazole and 10-chloro-5,6-dimethyl-5H-pyrido [3’,4’:4,5] pyrrolo [2,3-g] isoquinoline respectively, in 30 % overall yields. 1-Functionalized 11-nor-ellipticiner and analogues are thus obtained a two-step convergent pathway which appears to be particularly attractive for the rapid synthesis of various condensed heterocyclic systems.