A Versatile Synthesis of 3-Substituted 4-Cyano-1,2,3,4-tetrahydro-1-oxo-β-carbolines

Abstract

In a project aimed at the synthesis of analogues of the cytotoxic β-carboline alkaloid bauerine C with more advantageous solubility properties, a 3-amino analogue was prepared by treating ethyl 3-(cyanomethyl)indole-2-carboxylate with ammonia. Upon addition of aldehydes or ketones to the reaction mixture, 3-substituted 4-cyano-1,2,3,4-tetrahydro-1-oxo-β-carbolines were obtained in a one-pot condensation. When cyclic ketones are used, the procedure allows a convenient synthesis of tetracyclic spiro compounds.

Key words

β-carbolines - cyclizations - multicomponent reactions - indoles - lactams

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