K. Huber, O. Kast, F. Bracher
Nov 1, 2010
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Influential Citations
3
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Journal
Synthesis
Abstract
In a project aimed at the synthesis of analogues of the cytotoxic β-carbolinealkaloid bauerine C with more advantageous solubility properties,a 3-amino analogue was prepared by treating ethyl 3-(cyanomethyl)indole-2-carboxylatewith ammonia. Upon addition of aldehydes or ketones to the reactionmixture, 3-substituted 4-cyano-1,2,3,4-tetrahydro-1-oxo-β-carbolineswere obtained in a one-pot condensation. When cyclic ketones areused, the procedure allows a convenient synthesis of tetracyclicspiro compounds.