Russian Chemical Bulletin

, Volume 51, Issue 10, pp 1886–1893

α-Oxolactam enamines as new synthons in the Nenitzescu reaction

Authors

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

DOI: 10.1023/A:1021308719984

Cite this article as:
Lyubchanskaya, V.M., Alekseeva, L.M., Savina, S.A. et al. Russian Chemical Bulletin (2002) 51: 1886. doi:10.1023/A:1021308719984

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 enaminesNenitzescu reactionbenzofuropyridinesbenzofuroazepineschromenopyridines

Copyright information

© Plenum Publishing Corporation 2002