Citation: Arash Ghorbani-Choghamarani, Mohsen Nikoorazm, Gouhar Azadi. One-pot and novel route for the synthesis of 4-substituted-1,2,4-triazolidine-3,5-diones[J]. Chinese Chemical Letters, ;2014, 25(3): 451-454. doi: 10.1016/j.cclet.2013.11.020 shu

One-pot and novel route for the synthesis of 4-substituted-1,2,4-triazolidine-3,5-diones

1.
Department of Chemistry, Faculty of Science, Ilam University, Ilam 69315516, Iran

Corresponding author: Arash Ghorbani-Choghamarani,
Received Date: 5 September 2013
Available Online: 4 November 2013
Fund Project:

The efficient and one-pot synthesis of 4-substituted-1,2,4-triazolidin-3,5-dione derivatives (4-substituted urazoles) via combination of triphosgene, substituted anilines, and ethyl carbazate in the presence of cesium carbonate is presented.
- Urazole,
- Triphosgene,
- Aniline,
- Ethyl carbazate,
- Cesium carbonate
1. [1]
  [1] S. Mallakpour, Z. Rafiee, A novel one-pot synthesis of 4-substituted 1,2,4-triazolidine-3,5-diones, Synlett (2007) 1255-1256.
2. [2]
  [2] R. Simlot, R.A. Izydore, O.T. Wong, A.H. Hall, Hypolipidemic activity of 4-substituted 1,2-diacyl-1,2,4-triazolidine-3,5-diones in rodents, J. Pharm. Sci. 83 (1994) 367-371.
3. [3]
  [3] V. Kanagarajan, J. Thanusu, M.R. Ezhilarasi, M. Gopalakrishnan, Solvent-free one pot synthesis, characterization, antibacterial and antifungal activities of novel spiropiperidinyl-1,2,4-triazolidine-3-thiones, Chem. Heterocycl. Compds. 47 (2011) 60-66.
4. [4]
  [4] S. Mallakpour, Z. Rafiee, Ionic liquids as novel and green media for clean synthesis of soluble aromatic-aliphatic poly(amide-ester)s containing hydroxynaphthalene urazole moiety, Polym. Adv. Technol. 19 (2008) 1015-1023.
5. [5]
  [5] S. Mallakpour, Z. Rafiee, Solid-state polymerization of 4-(4-dimethylaminophenyl)-urazole with diisocyanates, Polym. Bull. 60 (2008) 507-514.
6. [6]
  [6] S. Mallakpour, Z. Rafiee, Efficient combination of ionic liquids and microwave irradiation as a green protocol for polycondensation of 4-(3-hydroxynaphthalene) 1,2,4-triazolidine-3,5-dionewith diisocyanates, Polymer48(2007) 5530-5540.
7. [7]
  [7] D.A. Gianolio, M. Lanfranchi, F. Lusardi, L. Marchio, M.A. Pellinghelli, Synthesis and characterization of Co(Ⅱ), Ni(Ⅱ), Cu(Ⅱ) and Zn(Ⅱ) complexes of 4-amino-1,2,4-triazolidine-3,5-dione (urazine), Inorg. Chim. Acta 309 (2000) 91-102.
8. [8]
  [8] S. Mallakpour, Z. Rafiee, Novel and efficient synthesis of 4-substituted-1,2,4-triazolidine-3,5-diones from anilines, Synth. Commun. 37 (2007) 1927-1934.
9. [9]
  [9] K.H. Park, L.J. Cox, Solid-phase synthesis of 1,2,4-triazolidine-3,5-diones, Tetrahedron Lett. 43 (2002) 3899-3901.
10. [10]
  [10] A. Ghorbani-Choghamarani, M.A. Zolfigol, P. Salehi, et al., An efficient procedure for the synthesis of Hantzsch 1,4-dihydropyridines under mild conditions, Acta Chim. Slov. 55 (2008) 644-647.
11. [11]
  [11] A. Ghorbani-Choghamarani, M. Hajjami, H. Goudarziafshar, et al., Catalytic oxidation of urazoles and bisurazoles to their corresponding triazolinediones using aluminium nitrate and a catalytic amount of silica sulfuric acid, Monatsh. Chem. 140 (2009) 607-610.
12. [12]
  [12] A. Ghorbani-Choghamarani, M.A. Zolfigol, M. Hajjami, et al., Nano aluminium nitride as a solid source of ammonia for the preparation of Hantzsch 1,4-dihydropyridines and bis-(1,4-dihydropyridines) in water via one pot multicomponent reaction, J. Braz. Chem. Soc. 22 (2011) 525-531.
13. [13]
  [13] A. Ghorbani-Choghamarani, Z. Chenani, S. Mallakpour, Supported nitric acid on silica gel and polyvinyl pyrrolidone (PVP) as an efficient oxidizing agent for the oxidation of urazoles and bis-urazoles, Synth. Commun. 39 (2009) 4264-4270.
14. [14]
  [14] A. Ghorbani-Choghamarani, M. Hajjami, M. Norouzi, et al., Diastereoselective and one-pot synthesis of trans-isoquinolonic acids via three-component condensation of homophthalic anhydride, aldehydes, and ammonium acetate catalyzed by aspartic acid, Tetrahedron 69 (2013) 6541-6544.
15. [15]
  [15] A. Ghorbani-Choghamarani, P. Zamani, Three component reactions: an efficient and green synthesis of 3,4-dihydropyrimidin-2-(1H)-ones and thiones using silica gel-supported l-pyrrolidine-2-carboxylic acid-4-hydrogen sulfate, Chin. Chem. Lett. 69 (2013) 804-808.
16. [16]
  [16] Y.C. Charalambides, S.C. Moratti, Comparison of base-promoted and self-catalyzed conditions in the synthesis of isocyanates from amines using triphosgene, Synth. Commun. 37 (2007) 1037-1044.
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