DIOXOTHIETANYLATION OF HETEROCYCLES. 1. <i>N</i>-(1,1-DIOXOTHIETAN-3-YL)-1,2,4-TRIAZOLES

Abstract

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.

Authors: E. E. Klen, N. N. Makarova, and F. A. Khaliullin

English Translation in Chemistry of Heterocyclic Compounds, 2013, 48 (10), pp 1473-1476

http://link.springer.com/article/10.1007/s10593-013-1159-7