Zinc-promoted direct amination of nitropyridines with methoxyamine via vicarious nucleophilic substitution

Abstract

Direct amination of nitropyridines with methoxyamine in the presence of a stoichiometric amount of zinc(II) chloride under basic conditions proceeds to give aminonitropyridines.

References

1. (a) J. A. May, Jr. and L. B. Townsend, J. Org. Chem., 1976, 41, 1449; (b) K. B. de Roos and C. A. Salemink, Recueil, 1969, 88, 1263; (c) J. B. Campbell, J. M. Greene, E. R. Lavagnino, D. N. Gardner, A. J. Pike and J. Snoddy, J. Heterocycl. Chem., 1986, 23, 669 and references cited therein.
2. R. A. Abramovitch and J. G. Saha, Adv. Heterocycl. Chem., 1966, 6, 229.
3. D. A. de Bie, B. Geurtsen and H. C. van der Plas, J. Org. Chem., 1985, 50, 484.
4. M. Wozniak, A. Baranski and B. Szpakiewicz, Liebigs Ann. Chem., 1991, 875.
5. M. Makosza and K. Wojciechowski, Liebigs Ann./Recueil, 1997, 1805.
6. (a) A. R. Katritzky and K. S. Laurenzo, J. Org. Chem., 1986, 51, 5039; (b) A. R. Katritzky and K. S. Laurenzo, J. Org. Chem., 1988, 53, 3978; (c) M. Makosza and M. Bialecki, J. Org. Chem., 1992, 57, 4784; (d) P. F. Pagoria, A. R. Mitchell and R. D. Schmidt, J. Org. Chem., 1996, 61, 2934.
7. M. Makosza and J. Winiarski, Acc. Chem. Res., 1987, 20, 282.
8. J. H. Boyer and W. Schoen, J. Am. Chem. Soc., 1956, 78, 423.
9. T. C. Bissot, R. W. Parry and D. H. Campbell, J. Am. Chem. Soc., 1957, 79, 796.
10. S. Seko and N. Kawamura, J. Org, Chem., 1996, 61, 442.
11. N. R. Ayyangar, S. N. Naik and K. V. Srinivasan, Tetrahedron Lett., 1990, 31, 3217.
12. J. Meisenheimer and E. Patzig, Chem. Ber., 1906, 39, 2533; H. E. Baumgarten, J. Am. Chem. Soc., 1955, 77, 5109; O. N. Chupakhin, V. N. Charushin and H. C. van der Plas, Tetrahedron, 1988, 44, 1; H. C. van der Plas, M. Wozniak and H. J. W. van der Haak, Adv. Heterocycl. Chem., 1983, 33, 95; R. Nasielski-Hinkens, J. Kotel, T. Lecloux and J. Nasielski, Synth. Commun., 1989, 19, 511.