Laboratoire de Pharmacognosie, Université Paris Descartes, Faculté des Sciences Pharmaceutiques et Biologiques, UMR 8638 CNRS, Paris, France.
Org Biomol Chem. 2011 Oct 26;9(22):7780-90. doi: 10.1039/c1ob06108a. Epub 2011 Oct 5.
A six-step one-pot reaction was designed for synthesizing homodimeric 7-phenylindolo[3,2-a]carbazoles from 1H-indoles and β-nitrostyrenes, in the presence of SnCl(2)·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 β-nitrostyrene and formal intramolecular [4 + 2]-cycloaddition is proposed.
设计了一个六步一锅反应，用于从 1H-吲哚和β-硝基苯乙烯在 SnCl(2)·2H(2)O 的存在下合成同二聚体 7-苯基吲哚并[3,2-a]咔唑。反应在非常温和的条件下进行，得到了中等至良好收率的所需杂环。提出了一种前所未有的机制，涉及顺序吲哚二聚化、生成的 2,3'-联吲哚与β-硝基苯乙烯的区域选择性亲核共轭加成以及形式的分子内[4 + 2]-环加成。
