二苯基二碲介导的 o-乙烯基芳基异氰化物与有机二硫化物的光诱导分子内环化反应。

Photoinduced intramolecular cyclization of o-ethenylaryl isocyanides with organic disulfides mediated by diphenyl ditelluride.

机构信息

Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Nakaku, Sakai, Osaka 599-8531, Japan.

出版信息

J Org Chem. 2011 May 20;76(10):3880-7. doi: 10.1021/jo200299d. Epub 2011 Apr 18.

DOI:10.1021/jo200299d

PMID:21462977

Abstract

Photoinduced reaction of o-ethenylaryl isocyanides with organic disulfides in the presence of diphenyl ditellurides affords the corresponding bisthiolated indole derivatives via a radical cyclization process. The cyclization can proceed at room temperature upon visible-light irradiation and exhibits good tolerance to functional groups. Several organic disulfides also can be employed for this cyclization, and the corresponding bisthiolated indole derivatives are obtained selectively. In addition, the photoinduced reaction of o-ethenylaryl isocyanides with bis(2-aminophenyl) disulfide affords tetracyclic compounds in one portion.

摘要

在二苯基二碲存在下，烯丙基异氰化物与有机二硫化物的光诱导反应通过自由基环化过程生成相应的双硫代吲哚衍生物。该环化反应在可见光照射下可以在室温下进行，并且对官能团具有良好的耐受性。几种有机二硫化物也可用于此环化反应，并且可以选择性地获得相应的双硫代吲哚衍生物。此外，烯丙基异氰化物与双(2-氨基苯基)二硫化物的光诱导反应以一步法得到四环化合物。