Ultrasound Assisted Synthesis of 1,5-Disubstituted Tetrazoles Containing Propargyl or 2-Azidophenyl Moieties via Ugi-Azide Reaction

Abstract

A series of ten 1,5-disubstituted-1H-tetrazoles (1,5-DS-T) were synthesized via Ugi-azide isocyanide-based multicomponent reactions (IMCR) in low to good yields (30–85%), using propargyl amine or 2-azidobenzaldehyde as a component, and using ultrasound irradiation (USI) as an alternative energy source. 1,5-DS-T are useful heterocyclic moieties, present in many bioactive compounds and drugs. Moreover, 1,5-DS-T are used as bidentate ligands, in coordination chemistry, metal–organic framework science, bioimaging, photo-imaging, explosives, propellants, and high-energy materials. The generated products can be used as synthetic platforms for subsequent post-transformations.

Keywords

• 1,5-disubstituted-1<i>H</i>-tetrazoles
• isocyanide-based multicomponent reactions
• Ugi-azide
• ultrasound irradiation