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.
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References
Dömling A (2006) Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev 106: 17–89. doi:10.1021/cr0505728
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
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
Dömling A, Ugi I (2000) Multicomponent reactions with isocyanides. Angew Chem Int Ed 39: 3168–3210
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
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
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
Balasubramanian M, Keay JG, Scriven EFV, Shobana N (1994) Approches to the synthesis of 1-substituted 1,2,4-triazoles. Heterocycles 37: 1951–1975
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
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
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
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
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
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
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
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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
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DOI: https://doi.org/10.1007/s11030-009-9218-9