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.
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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
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
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
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
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
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
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
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
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
Uneyamma K, Yamashita F, Sugimoto K, et al. N, N′-Disubstituted trifluoroacetamidines for trifluoromethylated polynitrogen heterocycles. Tetrahedron Lett, 1990, 31: 2717–2718
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
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
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
Alizadeh A. Synthesis of some new 1,2,4-triazole derivatives by mitsunobu chemistry. Helv Chim Acta, 2005, 88: 2777–2780
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
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
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
Gillis B T, Daniher F. Reaction of azodicarboxylic acid esters with aldehyde monosubstituted hydrazones. J Org Chem, 1962, 27: 4001–4003
Gillis B T, Beck P E. Reaction of ethyl azodicarboxylate with conjugated dienes. J Org Chem, 1962, 27: 1947–1951
Franzus B, Surridge J H. Reaction of ethyl azodicarboxylate with 1,3- and 1,4-cyclohexadienes. J Org Chem, 1962, 27: 1951–1957
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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
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DOI: https://doi.org/10.1007/s11434-010-4018-2