3,5-Substituted 1-(1,1-dioxothietan-3-yl)-1,2,4-triazoles have been prepared by treating NH-1,2,4-tri-azole sodium salts with 3,5-dibromo-1-(1,1-dioxothietan-3-yl)-1,2,4-triazole (a novel dioxothietanylating reagent). The reactions occur regioselectively at the position 2 for 5-bromo-1,2,4-triazoles containing ethoxy-, isopropoxy-, or phenoxy groups at the position 3 and at position 1 for 3-methylsulfanyl-1,2,4-tri-azole. The reaction occurs nonselectively at positions 1 and 2 in the case of 3-methylsulfonyl-1,2,4-tri-azole and 5-bromo-3-(piperidin-1-yl)-1,2,4-triazole, to give the isomeric 3-R-5-R1- and 5-R-3-R1-1-(1,1-di-oxothietan-3-yl)-1,2,4-triazoles.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1583-1586, October, 2012.
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Klen, E.E., Makarova, N.N. & Khaliullin, F.A. Dioxothietanylation of Heterocycles 1. N-(1,1-Dioxothietan-3-yl)-1,2,4-triazoles. Chem Heterocycl Comp 48, 1473–1476 (2013). https://doi.org/10.1007/s10593-013-1159-7
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DOI: https://doi.org/10.1007/s10593-013-1159-7