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Isothiourea-mediated one-pot synthesis of functionalized pyridines.

ABSTRACT: Acids to bases: The synthesis of 2,4,6-trisubstituted pyridines from (phenylthio)acetic acid and a range of ?,?-unsaturated ketimines is reported. This process proceeds by intermolecular Michael addition/lactamization, thiophenol elimination, and N- to O-sulfonyl migration, giving 2-sulfonate-substituted pyridines which are readily derivatized to generate structural diversity.

SUBMITTER: Stark DG

PROVIDER: S-EPMC4065352 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature

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Isothiourea-mediated one-pot synthesis of functionalized pyridines.

Stark Daniel G DG Morrill Louis C LC Yeh Pei-Pei PP Slawin Alexandra M Z AM O'Riordan Timothy J C TJ Smith Andrew D AD

Angewandte Chemie (International ed. in English) 20130917 44

Acids to bases: The synthesis of 2,4,6-trisubstituted pyridines from (phenylthio)acetic acid and a range of α,β-unsaturated ketimines is reported. This process proceeds by intermolecular Michael addition/lactamization, thiophenol elimination, and N- to O-sulfonyl migration, giving 2-sulfonate-substituted pyridines which are readily derivatized to generate structural diversity. ...[more]

PMID: 24106063

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