Synthesis of 1H-1,2,3-triazoles:Studies on Selective Reduction of Ester Substituents
This work is the first thorough study of the regioselective reduction of esters of 1H-1,2,3-triazoles with sodium borohydride in methanol. It was found that C5 esters were reduced much faster than C4 esters, making this regioselective process a general reaction of triazole C4,C5-diesters. Preference for reduction at C5 is attributed to electronic factors, supported by theoretical considerations and by molecular modeling electrostatic potential Hartree-Fock PM3 calculations. Reduction of C5 esters was observed for all 1-substituted-1H-1,2,3-triazole-5-esters in this study. The time required for ...
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