Simple preparation of fused pyrrolo[2,3-b]pyrrolidinones and pyrrolo[2,3-c]pyridazinones 1

Abstract

4-Methyl-4-(dimethoxymethyl)pyrans 4b, 4c and 15, prepared from cyclohexane-1,3-diones 1 or 4-hydroxycoumarin 14, pyruvaldehyde dimethyl acetal 2b and malononitrile 3, are subjected to hydrolysis with HCl to give fused furofuranones 5 and 16, which are treated with amines or hydrazines to give fused pyrrolopyrrolidinones 9 and 18 and pyrrolopyridazinones 12.

References

1. Part of this work was reported in a preliminary communication Y. Okamoto, T. Okawara and M. Furukawa, Heterocycles, 1996, 43, 2353.
2. S. Takano and K. Ogasawara, in The Alkaloids, ed. A. Brossi, Academic Press, New York, 1989, vol. 36, pp. 224–251.
3. U. Axelsson, Acta Ophthalmol., Suppl., 1969, 102, 1; M. B. Walker, Lancet, 1934, 226, 1200.
4. cf. S. A. Beller, J. E. Overall and A. C. Swann, Psychopharmacology, 1987, 87, 145.
5. Q. S. Yu and B.-Y. Lu, Heterocycles, 1994, 39, 519 and references cited therein P. F. Santos, A. M. Lobo and S. Prabhakar, Tetrahedron Lett., 1995, 36, 8099; X.-F. Pei and A. Brossi, Heterocycles, 1995, 41, 2823; M. Node, X.-J. Hao, K. Nishide and K. Fuji, Chem. Pharm. Bull., 1996, 44, 715.
6. F. F. Abdel-Latif, M. M. Mashaly and E. H. El-Gawish, J. Chem. Res. (S), 1995, 178.
7. T. Okawara, K. Uchiyama, Y. Okamoto, T. Yamasaki and M. Furukawa, J. Chem. Soc., Chem. Commun., 1990, 1385; T. Okawara, S. Ehara, S. Matsumoto, Y. Okamoto and M. Furukawa, J. Chem. Soc., Perkin Trans. 1, 1990, 2615; T. Okawara, S. Ehara, M. Eto, K. Harano and M. Furukawa, Tetrahedron Lett., 1993, 34, 4231; T. Okawara, S. Ehara, H. Kagotani, Y. Okamoto, M. Eto, K. Harano, T. Yamasaki and M. Furukawa, J. Org. Chem., 1996, 61, 4125.
8. J. P. Marino, S. Bogdan and K. Kimura, J. Am. Chem. Soc., 1992, 114, 5566.