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Note | Special issue | Vol 47, No. 2, 1998, pp.991-1004
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)64
Some Applications of the Regioselective Lithiation of α-Carbolines

Cyril Papamicaël, Georges Dupas,* Guy Quéguiner, and Jean Bourguignon

*Laboratoire de Chimie Organique Fine et Heterocyclique de l'IRCOF, UPRESA 6014 CNRS, INSA de Rouen, BP08, 76131, Mont-Saint-Aignan Cedex, France

Abstract

Regioselective metallation of the 3-carboxamido-α-carboline (1) afforded various 4-substituted-3-carboxamido-α-carbolines. Subsequent cross-coupling methodology applied to the 4-iodo-3-carboxamido-α-carboline (2e) led to 4-aryl-3-carboxamido-α-carbolines. Regioselective lithiation of 3-pivalamido-α-carboline led to 3,4-diaminopyrido[2,3-b]indole (7). Condensation of this diamine with (dichloromethylene)dimethylammonium chloride was then studied and an unusual reaction was observed. Some derivatives of imidazopyrido[2,3-b]indole were thus obtained.