Metal free synthesis of substituted 5-aryl/alkyl aminotetrazoles in water

Abstract

The synthesis of tetrazoles is established under metal free conditions at room temperature in the presence of open air. The reaction of 2-bromoaryl isothiocyantes with amines gives thiourea that undergoes reaction in situ with NaN3 using Iodine in the presence of water medium to afford 1-(2-bromophenyl)-N-5-arylaminotetrazoles via substitution followed by electrocyclization processes at ambient temperature. All electron donating and withdrawing substituents readily underwent the reaction to get the corresponding final products 2a–2ab in moderate to good yield. This methodology has also applied for gram-scale quantity of tetrazoles. In addition, our aqueous micellar medium has shown good recyclability activity and it has exhibited good yield of the product up to four cycles.