3-(1,3-BENZOTHIAZOL-2-YLSULFANYL)-1,2,6-THIADIAZINONES: SURROGATES FOR 3-HALO-1,2,6-THIADIAZINONES

Abstract

3,5-Bis(1,3-benzothiazol-2-ylsulfanyl)-4H-1,2,6-thiadiazin-4-one reacts with oxygen and nitrogen nucleophiles to give products with one of the 1,3-benzothiazol-2-ylsulfanyl groups displaced. The observed reactivity demonstrates that benzothiazole 2-sulfide behaves as a pseudohalide nucleofuge and was exploited to overcome the problematic displacement of chloride in 3-(1,3-benzothiazol-2-ylsulfanyl)-5-chloro-4H-1,2,6-thiadiazin-4-one.