Free radical cyclization reactions of allylsulfonyl substituted N-aryl amide derivatives

Che Ping Chuang, An I. Tsai, Ming Yi Tsai

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

p-Toluenesulfonyl radical can be generated by the manganese(III) acetate oxidation of sodium p-toluenesulfinate. The corresponding alkyl radicals could be produced effectively by the p-toluenesulfonyl radical induced radical reaction of allylsulfonyl substituted N-aryl amides. These alkyl radicals undergo 5-exo-trig, 6-endo-trig, or 6-exo-trig cyclization onto the aromatic ring effectively. The product distribution is highly dependent on the substituent of aromatic ring and the stability of radical intermediate. This p-toluenesulfonyl radical induced reaction provides a synthetically useful method for the synthesis of dihydroquinolinones, azaspirocyclic cyclohexadienes, and spirodihydroquinolinones.

Original languageEnglish
Pages (from-to)3293-3301
Number of pages9
JournalTetrahedron
Volume69
Issue number15
DOIs
Publication statusPublished - 2013 Apr 15

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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