Synthesis of 5-substituted 1-hydroxy-1,2,3-triazoles through directed lithiation of 1-(benzyloxy)-1,2,3-triazole

A study was conducted to characterize the synthesis of 5-substituted 1-hydroxy-1,2,3-triazoles by selective benzylation. O-Benzyl and O-carbamoyl-protected N-hydroxypyrazoles were prepared in good yields and were utilized in the metalation reactions while benzyl azide was reacted with acetylenedicarboxylic acid. Results indicated that hydrogen bonding to N-7 increased the catalytic effect of 7-aza 1-hydroxybenzotriazoles.