Russian Chemical Bulletin

, Volume 51, Issue 10, pp 1886–1893

α-Oxolactam enamines as new synthons in the Nenitzescu reaction

  • V. M. Lyubchanskaya
  • L. M. Alekseeva
  • S. A. Savina
  • A. S. Shashkov
  • V. G. Granik

Abstract

α-Oxolactam enamines, namely, 3-piperidino-5,6-dihydropyridin-2(1H)-one (1a) and 3-piperidino-1,5,6,7-tetrahydroazepin-2-one (1b), were introduced for the first time into the Nenitzescu reaction. The processes yield cyclic adducts 3a—e, 6. On heating in acetic acid, they are transformed into benzofuropyridone 7 and benzofuroazepinones 10a,d, and 12 and, unexpectedly, into chromenopyrrole 8 and chromenopyridines 9a—d and 11.

α-oxolactam enamines Nenitzescu reaction benzofuropyridines benzofuroazepines chromenopyridines 

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Copyright information

© Plenum Publishing Corporation 2002

Authors and Affiliations

  • V. M. Lyubchanskaya
    • 1
  • L. M. Alekseeva
    • 1
  • S. A. Savina
    • 1
  • A. S. Shashkov
    • 2
  • V. G. Granik
    • 1
  1. 1.Federal State Unitary Enterprise State Scientific Center “Scientific Research Institute of Organic Intermediates and Dyes”MoscowRussian Federation
  2. 2.Russian Academy of SciencesN. D. Zelinsky Institute of Organic ChemistryMoscowRussian Federation

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