Tetrahedron letters

A convenient modification of the Gassman oxindole synthesis

SW Wright, LD McClure, DL Hageman

Index: Wright, Stephen W.; McClure, Lester D.; Hageman, David L. Tetrahedron Letters, 1996 , vol. 37, # 27 p. 4631 - 4634

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Citation Number: 22

Abstract

A modification of the Gassman oxindole synthesis is described that proceeds from anilines and ethyl (methylsulfinyl) acetate, using oxalyl chloride to activate the sulfoxide to facilitate the formation of the key NS bonded intermediate. This procedure is particularly convenient for reactions carried out on smaller scales and for anilines that are susceptible to electrophilic halogenation.