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Communication | Regular issue | Vol 14, No. 1, 1980, pp.47-50
Published online, 1st January, 1970
DOI: 10.3987/R-1980-01-0047
Syntheses of Methyl 3-Alkyl-2-(2-benzamidophenyl)acrylates and Their Ring Closure to Indoline or Oxindole Derivatives

Shinji Kawai and Chikara Kaneko*

*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan

Abstract

Syntheses of methyl 3-dialkoxycarbonylmethyl- and -(α,α-dialkoxycarbonylethyl)-2-(2-benzamidophenyl)acrylates from methyl 2-phenyl-3,1-benzoxazepine-5-carboxylate were reported. Treatment of these two kinds of acrylates with base afforded entirely different products. Thus, while the former afforded 2,3-disubstituted indoline, the latter gave the oxindole, exclusively. The stereochemistries of the products as well as the mechanisms for these ring closure reactions are discussed.