Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 67, Issue 20, Pages 7048-7056Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0258857
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A variety of 3-substituted beta- and gamma-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 beta- and gamma-carbolines by either copper-catalyzed or thermal processes.
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