Skip to main content
Log in

One pot cascade synthesis of substituted 1,2,4-triazol-3-ones

  • Article
  • Organic Chemistry
  • Published:
Chinese Science Bulletin

Abstract

Substituted triazolinones were prepared by a three-component reaction of aldehydes, hydrazines and azodicarboxylates using TFA as a catalyst. The procedure was convenient and efficient, utilizing readily available substrates. A plausible mechanism for the cascade process is proposed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Refeences

  1. Demirbaş N, Uğurluoğlu R, Demirbaş R. Synthesis of 3-alkyl (aryl)-4-alkylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-ones and 3-alkyl-4-alkylamino-4,5-dihydro-1H-1,2,4-triazol-5-ones as antitumor agents. Bioorg Med Chem, 2002, 10: 3717–3723

    Article  Google Scholar 

  2. Katica C R, Vesna D, Vlado K, et al. Synthesis, antibacterial and antifungal activity of 4-substituted-5-aryl-1,2,4-triazoles. Molecules, 2001, 6: 815–824

    Article  Google Scholar 

  3. Yüksek H, Küçük M, Alkan M, et al. Synthesis and antioxidant activities of some new 4-(4-hydroxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives with their acidic properties. Asian J Chem, 2006, 18: 539–550

    Google Scholar 

  4. Yüksek H, Demibaş A, Ikizler A, et al. Synthesis and antibacterial activities of some 4,5-dihydro-1H-1,2,4-triazol-5-ones. Arzneim Forsch/Drug Res, 1997, 47: 405–409

    Google Scholar 

  5. Tozkoparan B, Gökhan N, Aktay G, et al. 6-benzylidenethiazolo [3,2-b]-1,2,4-triazole-5(6H)-ones substituted with ibuprofen: Synthesis, characterization and evaluation of anti-inflammatory activity. Eur J Med Chem, 2000, 35: 743–750

    Article  Google Scholar 

  6. Love B, Musser J H, Brown R E, et al. 1,2,4-triazolo [4,3-a]quinoxaline-1,4-diones as aniallergic agents. Med Chem, 1985, 28: 363–366

    Article  Google Scholar 

  7. Witkowski J T, Robins R K, Khare G P, et al. Synthesis and antiviral activity of 1,2,4-triazole-3-thiocarboxamide and 1,2,4-tieazole-3-carboxamidine ribonucleosides. J Med Chem, 1973, 16: 935–937

    Article  Google Scholar 

  8. Huang X H, Palani A, Xiao D, et al. Manipulation of N,O-nucleophilicity: Efficient formation of 4-N-substituted-2,4-dihydro-3H-1, 2,4-triazolin-3-ones. Org Lett, 2004, 6: 4795–4798

    Article  Google Scholar 

  9. Madding G D, Smith D W, Sheldon R I, et al. Synthesis and X-Ray crystal-structure of a 2,4,5-trisubstituted-1,2,4-triazolin-3-one J Heterocycl Chem, 1985, 22: 1121–1126

    Article  Google Scholar 

  10. Uneyamma K, Yamashita F, Sugimoto K, et al. N, N′-Disubstituted trifluoroacetamidines for trifluoromethylated polynitrogen heterocycles. Tetrahedron Lett, 1990, 31: 2717–2718

    Article  Google Scholar 

  11. Bartsch H, Erker T. Studies on the chemistry of O,N-containing and S, N-congtaing heterocycles 12 investigations on the synthesis of tricyclic 1,5-benzoxazepines. J Hererocycl Chem, 1990, 27: 991–993

    Article  Google Scholar 

  12. Shapiro R, DiCosimo R, Hennessey S M, et al. Discovery and development of a commercial synthesis of azafenidin. Org Proc Res Dev, 2001, 5: 593–598

    Article  Google Scholar 

  13. Romine J L, Martin S W, Gribkoff V K, et al. 4,5-diphenyltria-zol-3-ones: Openers of large-conductance Ca2+-activated potassium (maxi-K) channels. J Med Chem, 2002, 45: 2942–2952

    Article  Google Scholar 

  14. Alizadeh A. Synthesis of some new 1,2,4-triazole derivatives by mitsunobu chemistry. Helv Chim Acta, 2005, 88: 2777–2780

    Article  Google Scholar 

  15. Gruttadauria M, Buccheri F, Cusmano G, et al. Oxidative cyclization of some aldehyde semicarbazones induced by metallic salts. J Hererocycl Chem, 1993, 30: 765–770

    Article  Google Scholar 

  16. Nguyen T H, Milcent R, Barbier G. Oxidation of aldehyde semicarbazones with lead dioxide-application to the syntheses of 2-amino-1,3,4-oxadiazoles and 2,4-dihydro-1,2,4trialol-3-ones. J Hererocycl Chem, 1985, 22: 1383–1388

    Article  Google Scholar 

  17. Milcent R, Nguyen T H. Reactions on sulfur monochloride with some aromatic aldehyde semicarbazones and tthiosemicarbazones — new sytheses of subtituted-2,4-dihydro-1,2,4-triazol-3-ones, 2,4-dihydro-1,2,4-triazole-3-thiones and 2-amino-1,3,4-oxadiazoles. J Hererocycl Chem, 1986, 23: 881–883

    Article  Google Scholar 

  18. Gillis B T, Daniher F. Reaction of azodicarboxylic acid esters with aldehyde monosubstituted hydrazones. J Org Chem, 1962, 27: 4001–4003

    Article  Google Scholar 

  19. Gillis B T, Beck P E. Reaction of ethyl azodicarboxylate with conjugated dienes. J Org Chem, 1962, 27: 1947–1951

    Article  Google Scholar 

  20. Franzus B, Surridge J H. Reaction of ethyl azodicarboxylate with 1,3- and 1,4-cyclohexadienes. J Org Chem, 1962, 27: 1951–1957

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to YanGuang Wang.

About this article

Cite this article

Su, Y., Jiang, Z., Hong, D. et al. One pot cascade synthesis of substituted 1,2,4-triazol-3-ones. Chin. Sci. Bull. 55, 2879–2884 (2010). https://doi.org/10.1007/s11434-010-4018-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11434-010-4018-2

Keywords

Navigation