Additive and vinylogous Pummerer reactions of amido sulfoxides and their use in the preparation of nitrogen containing heterocycles

A Padwa, JT Kuethe

Index: Padwa, Albert; Kuethe, Jeffrey T. Journal of Organic Chemistry, 1998 , vol. 63, # 13 p. 4256 - 4268

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Citation Number: 40

Abstract

The α-thiocarbocation generated from the Pummerer reaction of N-methyl-N-phenyl-2-[2- (toluene-4-sulfinyl) phenyl] acetamide undergoes Friedel-Crafts reaction at the γ-carbon with the tethered aromatic ring. Reductive removal of the phenylthio group from the resulting product using Raney nickel occurs in high yield, and the overall reaction represents a new method for the synthesis of a variety of 3-phenyl-substituted oxindoles. Treatment of the ...