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  • Synthesis of indolines, indoles, and benzopyrrolizidinones from simple aryl azides.

Synthesis of indolines, indoles, and benzopyrrolizidinones from simple aryl azides.

Organic letters (2012-06-01)
François Brucelle, Philippe Renaud
ABSTRACT

A simple approach to prepare indolines and benzopyrrolizidinones from ortho-azidoallylbenzenes via a tandem radical addition/cyclization is described. The use of triethylborane to initiate and sustain the process provides the best results. Indolines are easily converted into the corresponding indoles by oxidation with manganese dioxide.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Indoline, ReagentPlus®, 99%