Regioselective 1,3-Dipolar Cycloaddition of Nitriles with Nitrile Imines Generated from Tetrazoles

A synthesis of 3,5-disubstituted-1,2,4-triazoles from nitriles and 5-aryltetrazoles is reported. When 5-aryltetrazoles are triflylated in the presence of nitriles, the resulting 5-aryl-2-triflyltetrazoles thermally generate N-triflyl-nitrile imines through a sequence of ring-chain tautomerization and denitrogenation. The N-triflyl-nitrile imines immediately undergo 1,3dipolar cycloaddition with nitriles in a regioselective manner, forming the corresponding 1,2,4-triazoles.

Automated summary

A method for the synthesis of 3,5-disubstituted-1,2,4-triazoles from nitriles and 5-aryltetrazoles is described. The reaction involves ring-chain tautomerization, denitrogenation, and 1,3-dipolar cycloaddition to achieve regioselective formation of the desired triazoles.