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Regioselective Reduction of 1H-1,2,3-Triazole Diesters.


ABSTRACT: Regioselective reactions can play pivotal roles in synthetic organic chemistry. The reduction of several 1-substituted 1,2,3-triazole 4,5-diesters by sodium borohydride has been found to be regioselective, with the C(5) ester groups being more reactive towards reduction than the C(4) ester groups. The amount of sodium borohydride and reaction time required for reduction varied greatly depending on the N(1)-substituent. The presence of a β-hydroxyl group on the N(1)-substituent was seen to have a rate enhancing effect on the reduction of the C(5) ester group. The regioselective reduction was attributed to the lower electron densities of the C(5) and the C(5) ester carbonyl carbon of the 1,2,3-triazole, which were further lowered in cases involving intramolecular hydrogen bonding.

SUBMITTER: Butler CR 

PROVIDER: S-EPMC8469956 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

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Regioselective Reduction of 1<i>H</i>-1,2,3-Triazole Diesters.

Butler Christopher R CR   Bendesky Justin J   Schoffstall Allen Milton AM  

Molecules (Basel, Switzerland) 20210915 18


Regioselective reactions can play pivotal roles in synthetic organic chemistry. The reduction of several 1-substituted 1,2,3-triazole 4,5-diesters by sodium borohydride has been found to be regioselective, with the C(5) ester groups being more reactive towards reduction than the C(4) ester groups. The amount of sodium borohydride and reaction time required for reduction varied greatly depending on the N(1)-substituent. The presence of a β-hydroxyl group on the N(1)-substituent was seen to have a  ...[more]

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