CBr4-Mediated Oxidative Desulfurization of N,N′-Disubstituted Thioureas: An Expedient Route to 5-Aminotetrazoles

Abstract

A highly efficient environmentally friendly synthetic method was developed to synthesize 5-amino­tetrazole derivatives through oxidative desulfurization of N,N′-disubstituted thiourea with sodium azide using carbon tetrabromide as a thiophilic reagent. The proposed protocol also offers a unique and convenient method for synthesizing 5-amino tetrazoles at room temperature without using any expensive reagent or toxic heavy metal salts by employing readily available, cheap, inexpensive, odorless, and easily handled bromine sources. The developed methodology involves very modest reaction conditions and affords easily isolable products with excellent yield.