General Method for the Synthesis of a-, b-, c- and d-Carbolines by Photo-induced Intramolecular Arylation of Anilidopiridines.

JOYDEV K. LAHA, SILVIA M. BAROLO, ROBERTO A. ROSSI*, AND GREGORY D. CUNY*

Anaheim, California

Congreso; 241st ACS National Meeting and Exposition; 2011

Carbolines (pyrido[x,y-b]indoles) exist as four different regioisomers and are found in a variety of natural and synthetic materials. Many of these compds. exhibit interesting biol. activities. Various synthetic approaches have previously been developed allowing access to the carboline regioisomers. However, a general strategy to the synthesis of all four isomers has been lacking. In this presentation a method for the synthesis of alpha-, beta-, gamma- and delta-carbolines from anilidopyridines using a photo-induced SRN1 reaction will be described. The anilidopyridine substrates were obtained from anilines and pyridines, or from halobenzenes and aminopyridines using palladium-catalyzed couplings. The various substituted carbolines were then obtained following intramol. C-C bond formation of the anilidopyridine anions in good to excellent yields.