Tetrahedron Letters

Rapid, robust, clean, catalyst-free synthesis of 2-halo-3-carboxyindoles

AR Kunzer, MD Wendt

Index: Kunzer, Aaron R.; Wendt, Michael D. Tetrahedron Letters, 2011 , vol. 52, # 15 p. 1815 - 1818

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Citation Number: 17

Abstract

A novel synthesis of 2-halo-3-carboxyindoles from 2-(2, 2-dihalovinyl) anilines was discovered. Reaction conditions and substrate applicability were studied. Optimally, the reaction takes only minutes when these substrates are heated in DMSO at 120° C in the presence of cesium carbonate. However, the reaction is robust and takes place at a wide range of temperatures, is tolerant of aqueous reaction conditions, and can be performed in ...