Intramolecular electrophilic cyclization of functional derivatives of unsaturated Compounds: I. Synthesis of 5-arylsulfanyl-6-phenylpiperidin-2-ones from cinnamylacetamides and arylsulfenyl chlorides

  • A. I. Vas’kevich
  • N. M. Tsizorik
  • E. B. Rusanov
  • V. I. Stanitets
  • M. V. Vovk
Article

Abstract

Sterically nonhindered N-alkyl(aryl)amides of cinnamylacetic acid in the reaction with phenyl(4-tolyl)sulfenyl chlorides in acetic acid in the presence of lithium perchlorate undergo a selective cyclization into 5-arylsulfanyl-6-phenylpiperidin-2-ones. Under similar conditions the reaction with arylsulfenyl chlorides of amides containing bulky substituents at the nitrogen atom resulted in 5-arylsulfanyl-6-phenyltetrahydropyran-2-iminium perchlorates, which by treatment with aqueous ethanol were converted into the corresponding derivatives of pyran-2-ones.

Keywords

Anhydrous Magnesium Sulfate Sulfanyl Lithium Perchlorate Piperidones Sulfenyl Chloride 

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Copyright information

© Pleiades Publishing, Ltd. 2011

Authors and Affiliations

  • A. I. Vas’kevich
    • 1
  • N. M. Tsizorik
    • 1
  • E. B. Rusanov
    • 1
  • V. I. Stanitets
    • 1
  • M. V. Vovk
    • 1
  1. 1.Institute of Organic ChemistryNational Academy of Sciences of UkraineKievUkraine

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