Tetrahedron letters

A general method for the synthesis of isatins: preparation of regiospecifically functionalized isatins from anilines

P Hewawasam, NA Meanwell

Index: Hewawasam, Piyasena; Meanwell, Nicholas A. Tetrahedron Letters, 1994 , vol. 35, # 40 p. 7303 - 7306

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Citation Number: 69

Abstract

Abstract A new method has been developed for regiospecific conversion of substituted anilines to isatins. The method utilizes the reaction of an ortho-lithiated, protected aniline derivative with diethyl oxalate to furnish an α-ketoester. Hydrolytic deprotection of the amino moiety is accompanied by cyclization to provide the isatin.