The Aza-ene Reaction of Heterocyclic Ketene Aminals with 4-Phenyl-1,2,4-triazoline-3,5-dione

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Jian-Heng Zhang, Mei-Xiang Wang and Zhi-Tang Huang


Abstract

Heterocyclic ketene aminals bearing a secondary enamine moiety underwent an efficient aza-ene reaction with 4-phenyl-1,2,4-triazoline-3,5-dione under very mild conditions, while no reaction was observed with their tertiary enamine analogues.


References

  1. (a) For reviews of ene reactions, see W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon Press, Oxford, 1990 Search PubMed; (b) B. B. Snide, Ene Reactions With Alkenes as Enophiles in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 5, ch. 1.1 Search PubMed.
  2. P. C. Montevecchi and M. L. Navacchia, J. Org. Chem., 1995, 60, 6455 CrossRef CAS.
  3. J. Cossy, A. Bouzide and M. Pfau, J. Org. Chem., 1997, 62, 7106 CrossRef CAS.
  4. J. E. Baldwin, R. M. Adlington, A. U. Jain, J. N. Kolhe and M. W. D. Perry, Tetrahedron, 1986, 42, 4247 CrossRef CAS.
  5. M.-X. Wang and Z.-T. Huang, J. Org. Chem., 1995, 60, 2807 CrossRef CAS and references therein.
  6. Z.-T. Huang and M.-X. Wang, J. Chem. Soc., Perkin Trans. 1, 1993, 1085 RSC.
  7. Org. Synth., 1988, Coll. Vol. 6, p. 936 Search PubMed.
  8. M.-Z. Deng, P. Caubere, J. P. Senet and S. Lecolier, Tetrahedron, 1988, 44, 6079 CrossRef CAS.
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