A Direct and General Synthesis of 5-Substituted 3-Trifluoromethyl-1,2,4-triazoles via the Three-component Condensation Reaction of Ethyl Trifluoroacetate, Hydrazine and Amidines

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Kazumasa Funabiki, Naoko Noma, Gouhaku Kuzuya, Masaki Matsui and Katsuyoshi Shibata


Abstract

The three component condensation reaction of ethyl trifluoroacetate, hydrazine and amidines in the presence of sodium hydroxide in tetrahydrofuran at reflux temperature gave the corresponding 3-trifluoromethyl-5-substituted 1,2,4-triazoles in good to excellent yields.


References

  1. For recent reviews, see: E. Differding, W. Frick, R. W. Lang, P. Martin, C. Schmit, S. Veenstra and H. Greuter, Bull. Soc. Chim. Belg., 1990, 99, 647 Search PubMed; M. J. Silvester, Adv. Heterocycl. Chem., 1994, 59, 1 CAS.
  2. For recent reports, see: K. Uneyama and K. Sugimoto, J. Org. Chem., 1992, 57, 6014 Search PubMed; M. Abdul-Ghani and A. E. Tipping, J. Fluorine Chem., 1990, 48, 149 CrossRef CAS; D. B. Reitz and M. J. Finkes, J. Heterocycl. Chem., 1989, 26, 225 CrossRef CAS; K. H. Pilgram and R. D. Skiles, J. Heterocycl. Chem., 1987, 24, 1265 CAS; K. H. Pilgram and R. D. Skiles, J. Heterocycl. Chem., 1983, 20, 1533 CAS for interesting reports for the structure basicity thermodynamic properties of trifluoromethylated azoles, see: A. E. Tipping, P. Jimenez, E. Ballesteros, J.-L. M. Abboud, M. Yánez, M. Esseffar and J. Elguero, J. Org. Chem., 1994, 59, 1039 CAS; B. G. Jones, S. K. Branch, A. S. Thompson and M. D. Threadgill, J. Chem. Soc., Perkin Trans. 1, 1996, 2685 Search PubMed; For recent synthetic applications of 3-trifluoromethyl-1,2,4-triazole, see: H. F. Zohdi, J. Chem. Res. (S), 1997, 392; 1998, 536 CrossRef CAS.
  3. Y. Yamaguchi, I. Katsuyama, K. Funabiki, M. Matsui and K. Shibata, J. Heterocycl. Chem., 1998, 35, 805 CrossRef CAS; I. Katsuyama, S. Ogawa, H. Nakamura, Y. Yamaguchi, K. Funabiki, M. Matsui, H. Muramatsu and K. Shibata, Heterocycles, 1998, 48, 779 CAS; I. Katsuyama, S. Ogawa, Y. Yamaguchi, K. Funabiki, M. Matsui, H. Muramatsu and K. Shibata, Synthesis, 1997, 1321 CrossRef CAS; I. Katsuyama, K. Funabiki, M. Matsui, H. Muramatsu and K. Shibata, Synlett, 1997, 591 CAS; I. Katsuyama, K. Funabiki, M. Matsui, H. Muramatsu and K. Shibata, Tetrahedron Lett., 1996, 37, 4177 CrossRef CAS.
  4. J. E. Francis, L. A. Gorczyca, G. C. Mazzenga and H. Meckler, Tetrahedron Lett., 1987, 28, 5133 CrossRef CAS.
  5. Z. Rappoport, Handbook of Tables for Organic Compound Identification, CRC, Ohio, 3rd edn., 1976, p. 436 Search PubMed.