Home Domino synthesis of novel series of 4-substituted 5-thioxo-1,2,4-triazolidin-3-one derivatives
Article
Licensed
Unlicensed Requires Authentication

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

  • Arash Ghorbani-Choghamarani EMAIL logo and Sara Sardari
Published/Copyright: July 27, 2012
Become an author with De Gruyter Brill

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.

[1] 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. http://dx.doi.org/10.1021/jo01098a60710.1021/jo01098a607Search in Google Scholar

[2] 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. http://dx.doi.org/10.1021/jm801503n10.1021/jm801503nSearch in Google Scholar PubMed PubMed Central

[3] 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. Search in Google Scholar

[4] 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. http://dx.doi.org/10.1080/0039791090289861910.1080/00397910902898619Search in Google Scholar

[5] 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. http://dx.doi.org/10.1007/s00706-008-0100-810.1007/s00706-008-0100-8Search in Google Scholar

[6] 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. http://dx.doi.org/10.2174/15701781079111245010.2174/157017810791112450Search in Google Scholar

[7] 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. http://dx.doi.org/10.1590/S0103-5053201100030001610.1590/S0103-50532011000300016Search in Google Scholar

[8] 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. 10.1055/s-2007-977413Search in Google Scholar

[9] 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. http://dx.doi.org/10.1021/cc020013410.1021/cc0200134Search in Google Scholar PubMed

[10] 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. Search in Google Scholar

[11] 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. http://dx.doi.org/10.1002/jps.260083032010.1002/jps.2600830320Search in Google Scholar PubMed

Published Online: 2012-7-27
Published in Print: 2012-11-1

© 2012 Institute of Chemistry, Slovak Academy of Sciences

Articles in the same Issue

  1. Immobilization in biotechnology and biorecognition: from macro- to nanoscale systems
  2. Bond-graph description and simulation of membrane processes: Permeation in a compartmental membrane system
  3. Design simulations for a biogas purification process using aqueous amine solutions
  4. Experimental and numerical investigation of pressure drop coefficient and static pressure difference in a tangential inlet cyclone separator
  5. Trace elements in Variegated Bolete (Suillus variegatus) fungi
  6. N,N′-methylenedipyridinium Pt(II) and Pt(IV) hybrid salts: synthesis, crystal and molecular structures of [(C5H5N)2CH2] · [PtCl4] and [(C5H5N)2CH2] · [PtCl6]
  7. Formation of membranes based on polyacrylonitrile and butadiene-acrylonitrile elastomer in the presence of copper ions
  8. One-step synthesis of solid sulfonic acid catalyst and its application in the acetalization of glycerol: crystal structure of cis-5-hydroxy-2-phenyl-1,3-dioxane trimer
  9. Mechanistic insights into the reaction of CF3CCl3 with SO3: Theory and experiment
  10. Near-infrared imaging for quantitative analysis of active component in counterfeit dimethomorph using partial least squares regression
  11. Corrosion of titanium diboride in molten FLiNaK(eut)
  12. Domino synthesis of novel series of 4-substituted 5-thioxo-1,2,4-triazolidin-3-one derivatives
  13. Erratum to: “Nguyen Hoang Loc, Nguyen Thanh Giang: Effects of elicitors on the enhancement of asiaticoside biosynthesis in cell cultures of centella (Centella asiatica L. Urban)”, Chemical Papers 66 (7) 642–648 (2012)
Downloaded on 25.9.2025 from https://www.degruyterbrill.com/document/doi/10.2478/s11696-012-0228-1/html
Scroll to top button