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Domino synthesis of novel series of 4-substituted 5-thioxo-1,2,4-triazolidin-3-one derivatives

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Abstract

The efficient synthesis of 4-substituted 5-thioxo-1,2,4-triazolidin-3-one derivatives (4-substituted thiourazoles) via domino combination of thiophosgene, aliphatic or aromatic amines, and ethyl carbazate is presented.

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References

  • Bradsher, C. K., Brown, F. C., & Webster, S. T. (1958). Some 4-substituted thiourazoles. The Journal of Organic Chemistry, 23, 618–619. DOI: 10.1021/jo01098a607.

    Article  CAS  Google Scholar 

  • De, S. K., Stebbins, J. L., Chen, L. H., Riel-Mehan, M., Machleidt, T., Dahl, R., Yuan, H., Emdadi, A., Barile, E., Chen, V., Murphy, R., & Pellecchia, M. (2009). Design, synthesis, and structure-activity relationship of substrate competitive, selective, and in vivo active triazole and thiadiazole inhibitors of the c-Jun N-terminal kinase. Journal of Medicinal Chemistry, 52, 1943–1952. DOI: 10.1021/jm801503n.

    Article  CAS  Google Scholar 

  • Ghorbani-Choghamarani, A., Zolfigol, M. A., Salehi, P., Ghaemi, E., Madrakian, E., Nasr-Isfahani, H., & Shahamirian, M. (2008). An efficient procedure for the synthesis of Hantzsch 1,4-dihydropyridines under mild conditions. Acta Chimica Slovenica, 55, 644–647.

    CAS  Google Scholar 

  • Ghorbani-Choghamarani, A., Chenani, Z., & Mallakpour, S. (2009a). Supported nitric acid on silica gel and polyvinyl pyrrolidone (PVP) as an efficient oxidizing agent for the oxidation of urazoles and bis-urazoles. Synthetic Communications, 39, 4264–4270. DOI: 10.1080/00397910902898619.

    Article  CAS  Google Scholar 

  • Ghorbani-Choghamarani, A., Hajjami, M., Goudarziafshar, H., Nikoorazm, M., Mallakpour, S., Sadeghizadeh, F., & Azadi, G. (2009b). Catalytic oxidation of urazoles and bis-urazoles to their corresponding triazolinediones using aluminium nitrate and a catalytic amount of silica sulfuric acid. Monatshefte für Chemie, 140, 607–610. DOI: 10.1007/s00706-008-0100-8.

    Article  CAS  Google Scholar 

  • Ghorbani-Choghamarani, A., Zolfigol, M. A., Hajjami, M., Rastgoo, S., & Mallakpour, S. (2010). Metal-free oxidation of urazole and 1,4-dihydropyridine derivatives under mild and heterogeneous conditions by nitro urea, derived from urea nitrate, and silica sulfuric acid. Letters in Organic Chemistry, 7, 249–254.

    Article  CAS  Google Scholar 

  • Ghorbani-Choghamarani, A., Zolfigol, M. A., Hajjami, M., Goudarziafshar, H., Nikoorazm, M., Yousefi, S., & Tahmasbi, B. (2011). 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. Journal of the Brazilian Chemical Society, 22, 525–531.

    Article  CAS  Google Scholar 

  • Mallakpour, S., & Rafiee, Z. (2007). A novel one-pot synthesis of 4-substituted 1,2,4-triazolidine-3,5-diones. Synlett, 2007, 1255–1256. DOI: 10.1055/s-2007-977413.

  • Phoon, C. W., & Sim, M. M. (2002). Solid-phase syntheses of 1,2,4-trisubstituted urazole and thiourazole derivatives. Journal of Combinatorial Chemistry, 4, 491–495. DOI: 10.1021/cc0200134.

    Article  CAS  Google Scholar 

  • Shimizu, T., Hashimoto, N., Nakayama, I., Nakao, T., Mizutani, H., Unai, T., Yamaguchi, M., & Abe, H. (1995). A novel isourazole herbicide, fluthiacet-methyl, is a potent inhibitor of protoporphyrinogen oxidase after isomerization by glutathione S-transferase. Plant & Cell Physiology, 36, 625–632.

    CAS  Google Scholar 

  • Simlot, R., Izydore, R. A., Wong, O. T., & Hall, I. H. (1994). Hypolipidemic activity of 4-substituted 1,2-diacyl-1,2,4-triazolidine-3,5-diones in rodents. Journal of Pharmaceutical Sciences, 83, 367–371. DOI: 10.1002/jps.2600830320.

    Article  CAS  Google Scholar 

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Correspondence to Arash Ghorbani-Choghamarani.

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Ghorbani-Choghamarani, A., Sardari, S. Domino synthesis of novel series of 4-substituted 5-thioxo-1,2,4-triazolidin-3-one derivatives. Chem. Pap. 66, 1078–1081 (2012). https://doi.org/10.2478/s11696-012-0228-1

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  • DOI: https://doi.org/10.2478/s11696-012-0228-1

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