Alkylation of 4-Nitroimidazole-5-Thiol With Alpha,Omega-Dihalides to Form Bicyclic Derivatives

Abstract

The ammonium salt of 4-nitroimidazole-5-thiol is alkylated at N and S by 1,2-dichloroethane, 1,3-dibromopropane, and 1,4-dibromobutane to give bicyclic products. These cyclic thioethers can be oxidized to the sulfones , and brominated in the imidazole ring, while the bromine atom is subject to nucleophilic displacement by piperidine.