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铁催化合成氧化吲哚:在吡咯并吲哚啉制备中的应用。

Iron-Catalyzed Synthesis of Oxindoles: Application to the Preparation of Pyrroloindolines.

机构信息

Departament of Fundamental Chemistry, Institute of Chemistry, University of São Paulo , Av. Prof. Lineu Prestes 748, 05508-900, São Paulo, Brazil.

出版信息

Org Lett. 2017 Mar 3;19(5):1060-1063. doi: 10.1021/acs.orglett.7b00078. Epub 2017 Feb 20.

Abstract

A novel and highly efficient synthetic approach to pyrroloindolines has been developed. The process is based on tandem radical addition/cyclization with inexpensive iron catalyst. This method tolerates a wide range of N-methyl-N-arylacrylamides as well carbamoyl radicals, providing access to a variety of functionalized 3,3-disubstituted oxindoles, key intermediates for many bioactive pyrroloindolines such as (±)-esermethole, (±)-deoxyeseroline, and (±)-physovenol methyl ether.

摘要

一种新颖、高效的吡咯并吲哚啉合成方法已经被开发出来。该方法基于廉价铁催化剂的自由基加成/环化串联反应。这种方法对多种 N-甲基-N-芳基丙烯酰胺以及氨甲酰基自由基具有耐受性,为多种功能化 3,3-二取代氧化吲哚提供了途径,这些氧化吲哚是许多生物活性吡咯并吲哚啉(如(±)-esermethole、(±)-deoxyeseroline 和(±)-physovenol methyl ether)的关键中间体。

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