The Journal of organic chemistry

Synthesis of β-and γ-Carbolines by the palladium/copper-catalyzed coupling and cyclization of terminal acetylenes

H Zhang, RC Larock

Index: Zhang, Haiming; Larock, Richard C. Journal of Organic Chemistry, 2002 , vol. 67, # 20 p. 7048 - 7056

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Citation Number: 95

Abstract

A variety of 3-substituted β-and γ-carbolines have been synthesized from N-substituted 3- iodoindole-2-carboxaldehydes and 2-bromoindole-3-carboxaldehydes, respectively. The coupling of these aldehydes with various terminal acetylenes with PdCl2 (PPh3) 2/CuI as the catalyst readily affords the corresponding alkynylindole carboxaldehydes, which have subsequently been converted to the corresponding tert-butylimines and cyclized to β-and ...