1,3-Dipolar cycloadditions to methylenespiro[2.2]pentane: a complementary access to spiro cyclopropanated azaheterocycles

Abstract

The domino cycloaddition–thermal rearrangement of nitrile oxides and methylenespiro[2.2]pentane gives 5-azaspiro[2.5]oct-6-en-8-one derivatives; with a nitrone the process complements the one using bi(cyclopropylidene) for the synthesis of α-spiro cyclopropanated heterocyclic ketones.

References

1. A. Brandi, A. Goti, S. Kozhushkov and A. de Meijere, J. Chem. Soc., Chem. Commun., 1994, 2185; A. Goti, B. Anichini, A. Brandi, S. Kozhushkov, C. Gratkowski and A. de Meijere, J. Org. Chem., 1996, 61, 1665.
2. A. Goti, B. Anichini, A. Brandi, A. de Meijere, L. Citti and S. Nevischi, Tetrahedron Lett., 1995, 36, 5811.
3. W. R. Dolbier, Jr., K. Akiba, J. M. Riemann, C. A. Harmon, M. Bertrand, A. Bezaguet and M. Santelli, J. Am. Chem. Soc., 1971, 93, 3933.
4. (a) S. Arora and P. Binger, Synthesis, 1974, 801; (b) A. de Meijere and S. I. Kozhushkov, in Carbocyclic Three-Membered Ring Compounds, ed. A. de Meijere, Thieme, Stuttgart, 1996, vol. E17, in the press.
5. (a) A. Goti, F. M. Cordero and A. Brandi, Top. Curr. Chem., 1996, 178, 1; (b) N. S. Zefirov, S. I. Kozhushkov, B. I. Ugrak, K. A. Lukin, O. V. Kokoreva, D. S. Yufit, Y. T. Struchkov, S. Zoellner, R. Boese and A. de Meijere, J. Org. Chem., 1992, 57, 701.
6. S. Danishefsky, Acc. Chem. Res., 1979, 12, 66 and references cited therein.
7. (a) A. Brandi, F. M. Cordero, F. De Sarlo, A. Goti and A. Guarna, Synlett, 1993, 1; (b) F. M. Cordero, A. Brandi, C. Querci, A. Goti, F. De Sarlo and A. Guarna, J. Org. Chem., 1990, 55, 1762; (c) A. Brandi, S. Garro, A. Guarna, A. Goti, F. M. Cordero and F. De Sarlo, J. Org. Chem., 1988, 53, 2430.
8. D. C. Nonhebel, Chem. Soc. Rev., 1993, 347; J. Walton, in Carbocyclic Three-Membered Ring Compounds, ed. A. de Meijere, Thieme, Stuttgart, 1996, vol. E17, in the press; S.-Y. Choi and M. Newcomb, Tetrahedron, 1995, 51, 654; H. Venkatesan and M. M. Greenberg, J. Org. Chem., 1995, 60, 1053; D. J. Hastings and A. C. Weedon, J. Org. Chem., 1991, 56, 6326; D. Becker, N. Haddad and Y. Sahali, Tetrahedron Lett., 1989, 30, 2661.