Chemistry of Heterocyclic Compounds

, Volume 14, Issue 11, pp 1223–1226 | Cite as

Research on lactams

XXXII. Anomalous fischer reaction of α-oxocaprolactam O-phenyloxime
  • R. G. Glushkov
  • I. M. Zasosova
  • I. M. Ovcharova
  • N. P. Solov'eva
  • O. S. Anisimova
  • Yu. N. Sheinker
Article
  • 26 Downloads

Abstract

The reaction of O-phenylhydroxylamine hydrochloride with α-oxocaprolactam gave α-oxocaprolactam O-phenyloxime, which gave two substances -1,2,3,4-tetrahydro-pyrido[2,3-c]coumarin as the principal product and 1-oxo-10a-hydroxy-1H-2,3,4,5, 5a,10a-hexahydrobenzofuro[2,3-c]azepine as the minor product — under the conditions of the Fischer reaction. The minor product was converted to 1-oxo-1H-2,3, 4,5-tetrahydrobenzofuro[2,3-c]azepine in quantitative yield by dehydration in trifluoroacetic acid.

Keywords

Organic Chemistry Dehydration Hydrochloride Coumarin Trifluoroacetic Acid 

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Copyright information

© Plenum Publishing Corporation 1979

Authors and Affiliations

  • R. G. Glushkov
    • 1
  • I. M. Zasosova
    • 1
  • I. M. Ovcharova
    • 1
  • N. P. Solov'eva
    • 1
  • O. S. Anisimova
    • 1
  • Yu. N. Sheinker
    • 1
  1. 1.S. Ordzhonikidze All-Union Scientific-Research Pharmaceutical-Chemistry InstituteMoscow

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