Skip to main content
Log in

Synthesis of functionalized 1,2,4-triazole-3-thiones from ammonium isothiocyanate, acid chlorides, and arylhydrazines

  • Full-Length Paper
  • Published:
Molecular Diversity Aims and scope Submit manuscript

Abstract

An efficient synthesis of 1-aryl-5-aryl(alkyl)-1,2-dihydro-3H-1,2,4-triazole-3-thiones via reaction between ammonium thiocyanate, acid chlorides, and arylhydrazines is described.

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.

Institutional subscriptions

Similar content being viewed by others

References

  1. Dömling A (2006) Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev 106: 17–89. doi:10.1021/cr0505728

    Article  PubMed  Google Scholar 

  2. Hulme C, Gore V (2003) Multi-component reactions: emerging chemistry in drug discovery from xylocain to crixivan. Curr Med Chem 10: 51–80. doi:10.2174/0929867033368600

    Article  CAS  PubMed  Google Scholar 

  3. Zhu J (2003) Recent developments in the isonitrile-based multicomponent synthesis of heterocycles. Eur J Org Chem 2003: 1133–1144. doi:10.1002/ejoc.200390167

    Article  Google Scholar 

  4. Dömling A, Ugi I (2000) Multicomponent reactions with isocyanides. Angew Chem Int Ed 39: 3168–3210

    Google Scholar 

  5. Borg S, Estenne-Bouhtou G, Luthman K, Csoregh I, Hessellink W, Hacksell U (1995) Synthesis of 1,2,4-oxadiazole, 1,3,4-oxadiazole, and 1,2,4-triazole derived dipeptidomimetics. J Org Chem 60: 3112–3120. doi:10.1021/jo00115a029

    Article  CAS  Google Scholar 

  6. Garratt PJ (1996) A practical methylation procedure for (1H)-1,2,4-trazole. In: Katritzky AR, Rees CW, Sriven EFV (eds) Comprehensive heterocyclic chemistry II, vol 4. Elsevier, Oxford, pp 127–163 and 905–1006

  7. Turnbull K (1998) Five-membered ring systems with more than one nitrogen atom. In: Gribble GW, Joule JA (eds) Progress in heterocyclic chemistry, vol 10. Elsevier, Oxford, pp 153–171

    Google Scholar 

  8. Balasubramanian M, Keay JG, Scriven EFV, Shobana N (1994) Approches to the synthesis of 1-substituted 1,2,4-triazoles. Heterocycles 37: 1951–1975

    Article  CAS  Google Scholar 

  9. Angulo J, Serrano M, Henning L (2003) Synthesis and characterization of 1,5-diphenyl-1,2,4-triazole-thion. Rev Soc Quim Peru 69: 131–142

    Google Scholar 

  10. Dunstan AR, Weber HP, Rihs G, Widner H, Dziadulewicz EK (1998) Concise and regiospecific syntheses of tri-substituted 1,2,4-triazoles. Tetrahedron Lett 39: 7983–7986

    Article  CAS  Google Scholar 

  11. Tarasova OA, Klyba LV, Vvedensky VY, Nedolya NA, Trofimov BA, Brandsma L, Verkruijsse HD (1998) One-pot syntheses of 2-N-alkylamino-, 2-N-phenylamino-, 2-N,N-dialky-lamino-, and 2-N-alkyl-N-phenylaminothiophenes. Eur J Org Chem 253–256. doi:10.1002/(SICI)1099-0690(199802)1998:2<253::AID-EJOC253>3.0.CO;2-E

  12. Yavari I, Sabbaghan M, Hossaini Z (2007) Reaction between alkyl isocyanides and isopropylideneMeldrum’s acid in the presence of bidentate nucleophiles. Mol Divers 11: 1–5. doi:10.1007/s11030-006-9052-2

    Article  CAS  PubMed  Google Scholar 

  13. Yavari I, Sirouspour M, Souri S (2006) Three-component synthesis of functionalized 5-oxo-4,5-dihydroindeno[1,2-b]pyrans. Mol Divers 10: 265–270. doi:10.1007/s11030-006-9022-8

    Article  CAS  PubMed  Google Scholar 

  14. Yavari I, Zabarjad-Shiraz N (2006) Three-component reaction between triphenylphosphine, dialkyl acetylenedicarboxylates and urea or N-methylurea. Mol Divers 10: 23–27. doi:10.1007/s11030-009-9128-x

    Article  CAS  PubMed  Google Scholar 

  15. Yavari I, Hossaini Z, Souri S, Sabbaghan M (2008) N-Methylimidazole-promoted efficient synthesis of functionalized 1,3-oxazoline-2-thiones under solvent-free conditions. Synlett 9: 1287–1288. doi:10.1055/s2008-1078403

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Issa Yavari.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yavari, I., Shirgahi-Talari, F., Hossaini, Z. et al. Synthesis of functionalized 1,2,4-triazole-3-thiones from ammonium isothiocyanate, acid chlorides, and arylhydrazines. Mol Divers 14, 763–766 (2010). https://doi.org/10.1007/s11030-009-9218-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11030-009-9218-9

Keywords

Navigation