A one-pot synthesis of 7-phenylindolo[3,2-a]carbazoles from indoles and beta-nitrostyrenes, via an unprecedented reaction sequence

作者:Dupeyre Gregory; Lemoine Pascale; Ainseba Nabila; Michel Sylvie; Cachet Xavier*
来源:Organic and Biomolecular Chemistry, 2011, 9(22): 7780-7790.
DOI:10.1039/c1ob06108a

摘要

A six-step one-pot reaction was designed for synthesizing homodimeric 7-phenylindolo[3,2-a]carbazoles from 1H-indoles and beta-nitrostyrenes, in the presence of SnCl2 center dot 2H(2)O. The reactions proceeded under very mild conditions and the desired heterocycles were obtained in moderate to good yields. An unprecedented mechanism involving sequential indole dimerization, regioselective nucleophilic conjugate addition of the resulting 2,3'-biindole to beta-nitrostyrene and formal intramolecular [4 + 2]-cycloaddition is proposed.

  • 出版日期2011