An Efficient One Pot Synthesis of Bicyclic Dienones

Abstract

Bicyclic dienones 4 are prepared in a one pot process from the reaction of 2-(acetoxymethyl)cyclohex-2-enone 1 with 1,3-dicarbonyl compounds 2 in the presence of K₂CO₃ in refluxing absolute ethanol.

References

1. R. C. Klix and R. D. Bach, J. Org. Chem., 1987, 52, 580.
2. W. von E. Doering, L. Birladeanu, X. Cheng, T. Kitagawa and K. Sarma, J. Am. Chem. Soc., 1991, 113, 4558.
3. J. Colonge and P. Brison, Bull. Soc. Chim. Fr., 1961, 98.
4. F. Rezgui and M. M. El Gaïed, Tetrahedron, 1997, 53, 15711 and references cited therein.
5. A. B. Smith, III, B. D. Dorsey, M. Ohba, A. T. Lupo, Jr. and M. S. Malamas, J. Org. Chem., 1988, 53, 4314; F. Rezgui and M. M. El Gaïed, Tetrahedron Lett., 1998, 39, 5965.
6. I. Takao, K. Kunimoto, S. Masanobu, N. Kiyohino and N. Takemitsu, Chem. Abstr., 1987, 106, 49660m.
7. R. E. Gawley, Synthesis, 1976, 777.
8. Et₃N (1 equiv.) was used to obtain 3d and 3e which were converted in situ by addition of K₂CO₃(2 equiv.) into 4d and 4e(both equivalent to 4a), respectively; spectroscopic data for compounds 3d and 3e are consistent with those reported in ref. 4.
9. A. Chamekh and H. Amri, Tetrahedron Lett., 1998, 39, 375.