Diels–Alder trapping of an o-dinitroso intermediate in the 1-oxide/3-oxide interconversion of a 2,1,3-benzoxadiazole derivative

Abstract

Convincing evidence is presented that the o-dinitroso intermediate involved in the exchange of the 1-oxide and 3-oxide tautomers of 6-nitro[2,1,3]oxadiazolo[4,5-b]pyridine 1-oxide 5 is the precursor of the Diels–Alder diadduct 7 isolated upon treatment of this compound with cyclohexadiene in CHCl₃.

References

1. F. Terrier, in Nucleophilic Aromatic Displacement, ed. H. Feuer, VCH, New York, 1991; F. Terrier, E. Kizilian, J. C. Hallé and E. Buncel, J. Am. Chem. Soc., 1992, 114, 1740.
2. E. Buncel, R. A. Manderville and J. M. Dust, J. Chem. Soc., Perkin Trans. 2, 1997, 1019 and numerous references therein.
3. W. P. Norris, R. J. Spear and R. W. Read, Aust. J. Chem., 1989, 36, 297.
4. J. Kund and H. J. Niclas, Synth. Commun., 1993, 23, 1569.
5. M. R. Crampton, L. C. Rabbit and F. Terrier, Can. J. Chem., 1999, 77 in the press.
6. M. I. Evgen'yev, S. Y. Garmonov, I. I. Evgen'yeva and L. S. Gazizullina, J. Anal. Chem., 1998, 53, 57 and references therein.
7. A. Gasco and A. J. Boulton, Adv. Heterocycl. Chem., 1981, 29, 252 and references therein.
8. F. Terrier, E. Kizilian, J. C. Hallé, M. J. Pouet and E. Buncel, J. Phys. Org. Chem., 1998, 11, 707 and references therein.
9. J. C. Hallé, D. Vichard, M. J. Pouet and F. Terrier, J. Org. Chem., 1997, 62, 7178; D. Vichard, J. C. Hallé, B. Huguet, M. J. Pouet, D. Riou and F. Terrier, Chem. Commun., 1998, 791; S. Pugnaud, D. Masure, J. C. Hallé and P. Chaquin, J. Org. Chem., 1997, 62, 8687; P. Sépulcri, R. Goumont, J. C. Hallé, D. Riou and F. Terrier, to be submitted.
10. C. K. Lowe-Ma, R. A. Nissan and W. S. Wilson, J. Org. Chem., 1990, 55, 3755.
11. R. K. Harris, A. R. Katritzky, S. Øksne, A. S. Bailey and G. Patterson, J. Chem. Soc., 1963, 197 and references therein I. Yavari, R. E. Botto and J. D. Roberts, J. Org. Chem., 1978, 43, 2542; F. A. L. Anet and I. Yavari, Org. Magn. Reson., 1976, 8, 158; M. Witanowski, L. Stefaniak, S. Biernat and G. A. Webb, Org. Magn. Reson., 1980, 14, 365; F. B. Mallory, S. L. Manatt and C. S. Wood, J. Am. Chem. Soc., 1965, 87, 5433; M. J. Haddadin and C. H. Issidorides, Tetrahedron Lett., 1965, 36, 3253.
12. J. K. Gallos and E. Malamidou-Xenikaki, Heterocycles, 1994, 37, 193; N. G. Argyropoulos, J. K. Gallos and D. N. Nicolaides, Tetrahedron, 1986, 42, 3631; A. B. Bulacinski, E. F. V. Scriven and H. Suschitzky, Tetrahedron Lett., 1975, 3577; J. W. McFarland, J. Org. Chem., 1971, 36, 1842.
13. I. R. Dunkin, M. A. Lynch, A. J. Boulton and N. Henderson, J. Chem. Soc., Chem. Commun., 1991, 1178; S. Murata and H. Tomioka, Chem. Lett., 1992, 57.
14. D. L. Boger and S. N. Weinreb, in Hetero Diels-Alder Methodology in Organic synthesis, Academic Press, New York, 1987, pp. 71–93.
15. P. Sépulcri, J. C. Hallé, R. Goumont, D. Riou and F. Terrier, unpublished results.