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A regioselective etherification of pyridoxine via an ortho-pyridinone methide intermediate.

ABSTRACT: The catalyst-free, regioselective synthesis of 4'-O-substituted pyridoxine derivatives under solventless conditions is described. The methodology relies on the highly regioselective formation of the ortho-pyridinone methide from pyridoxine and subsequent oxa-Michael addition of alcohol nucleophiles. This methodology provides good to excellent yields for primary and secondary alcohols and moderate yields for tertiary alcohols.

SUBMITTER: Yazarians JA

PROVIDER: S-EPMC7111860 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

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A regioselective etherification of pyridoxine via an ortho-pyridinone methide intermediate.

Yazarians Jessica A JA Jiménez Brian L BL Boyce Gregory R GR

Tetrahedron letters 20170425 23

The catalyst-free, regioselective synthesis of 4'-O-substituted pyridoxine derivatives under solventless conditions is described. The methodology relies on the highly regioselective formation of the ortho-pyridinone methide from pyridoxine and subsequent oxa-Michael addition of alcohol nucleophiles. This methodology provides good to excellent yields for primary and secondary alcohols and moderate yields for tertiary alcohols. ...[more]

PMID: 32287448

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