title: A new synthesis of benzo[b]thiophene-2-thiolates and their derivatives via base-promoted transformation of 4-(2-mercaptophenyl)-1,2,3-thiadiazoles.
abstract: A reaction of 4-(2-mercaptophenyl)-1,2,3-thiadiazoles with an oxidant in the presence of 1.1 equiv of base afforded good yields of benzo[4,5]thieno[3,2-d][1,2,3]thiadiazoles via the intramolecular oxidative nucleophilic substitution of a hydrogen (ONHS) pathway. The reaction of 4-(2-mercaptophenyl)-1,2,3-thiadiazoles in the presence of ≥2 equiv of base gave 2-mercaptobenzo[b]thiophenes via an anionic ring-opening/ring-closure pathway.
authors.affiliation: Department of Organic Chemistry, Saint-Petersburg State Institute of Technology, Moskovskii prospekt 26, Saint-Petersburg 190013, Russia.
authors.forename: Fedor S
authors.initials: FS
authors.lastname: Teplyakov
authors.forename: Tatiana G
authors.initials: TG
authors.lastname: Vasileva
authors.forename: Mikhail L
authors.initials: ML
authors.lastname: Petrov
authors.forename: Dmitry A
authors.initials: DA
authors.lastname: Androsov