Vicarious nucleophilic substitution of pyridazinium N-dicyanomethylides

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Takashi Itoh, Yûji Matsuya, Kazuhiro Nagata, Michiko Miyazaki, Nozomi Tsutsumi and Akio Ohsawa


Abstract

Pyridazines have been allowed to react with tetracyanoethylene oxide to give pyridazinium N-dicyanomethylides, which are subjected to vicarious nucleophilic substitution to afford the corresponding 4-substituted derivatives in moderate to good yields. The dicyanomethylene group is readily eliminated by a radical reaction, and 4-substituted pyridazines are obtained.


References

  1. W. J. Coates, in Comprehensive Heterocyclic Chemistry II, ed. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, ed. A. J. Boulton, Pergamon Press, Oxford, 1996, vol. 6, pp. 18–33 Search PubMed.
  2. (a) H. Hara and H. C. van der Plas, J. Heterocycl. Chem., 1982, 19, 1285 CAS; (b) W. Dostal and G. Heinisch, Heterocycles, 1986, 24, 793 CAS; (c) H. Yamazaki, H. Harada, K. Matsuzaki, K. Yoshida, M. Takase and E. Ohki, Chem. Pharm. Bull., 1987, 35, 3971; (d) H. Uno, S. Okada and H. Suzuki, Tetrahedron, 1991, 47, 6231 CrossRef CAS; (e) N. Plé, A. Turck, K. Couture and G. Quéguiner, J. Org. Chem., 1995, 60, 3781 CrossRef CAS.
  3. (a) M. Makosza, Synthesis, 1991, 103 CrossRef CAS; (b) M. Makosza and K. Wojciechowski, Liebigs Ann./Recueil, 1997, 1805 Search PubMed; (c) M. Makosza, Pure Appl. Chem., 1997, 69, 559 CAS.
  4. A. Ostrowicz, S. Batoniak, M. Makosza and A. Rykowski, Tetrahedron Lett., 1992, 33, 4787 CrossRef CAS.
  5. (a) T. Itoh, K. Nagata, M. Okada and A. Ohsawa, Chem. Pharm. Bull., 1993, 41, 220 CAS; (b) Heterocycles, 1993, 35, 581 Search PubMed; (c) K. Nagata, T. Itoh, M. Okada and A. Ohsawa, Chem. Pharm. Bull., 1993, 41, 1644 CAS.
  6. Preliminary communication; T. Itoh, Y. Matsuya, K. Nagata, M. Okada and A. Ohsawa, J. Chem. Soc., Chem. Commun., 1995, 2067 Search PubMed.
  7. W. J. Linn, O. W. Webster and R. E. Benson, J. Am. Chem. Soc., 1965, 87, 3651 CrossRef CAS.
  8. (a) Y. Kobayashi, T. Kutsuma, K. Morinaga, M. Fujita and Y. Hanzawa, Chem. Pharm. Bull., 1970, 18, 2489 CAS; (b) I. Cardinaud, A. Gueiffier, F. Fauvelle, J.-C. Milhavet and J.-P. Chapat, Heterocycles, 1993, 36, 1945 CAS.
  9. M. Makosza and J. Winiarski, Acc. Chem. Res., 1987, 20, 282 CrossRef CAS.
  10. F. Minisci, F. Fontana and E. Vismara, J. Heterocycl. Chem., 1990, 27, 29 and references cited therein.
  11. M. Makosza, personal communication.
  12. N. S. Simpkins, Sulphones in Organic Synthesis, Pergamon Press, Oxford, 1993, pp. 100–182 Search PubMed.
  13. J. J. P. Stewart, J. Comput. Chem., 1989, 10, 221 CrossRef CAS.
  14. Quantum Chemistry Program Exchange, No. 455, Indiana University, USA.
  15. Quantum Chemistry Program Exchange, No. 395, Indiana University, USA.
  16. M. J. S. Dewar and S. Kirschner, J. Am. Chem. Soc., 1971, 93, 4290 CrossRef CAS.
  17. J. W. McIver and A. Komornicki, J. Am. Chem. Soc., 1972, 94, 2625 CrossRef.
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