Polysubstituted Pyridines from 1,4-Oxazinone Precursors.

ABSTRACT: This study describes a general method for the preparation of 1,4-oxazin-2-one intermediates from acetylene dicarboxylate and β-amino alcohol precursors. Oxazinones prepared in this manner were employed in a tandem cycloaddition/cycloreversion reaction sequence with a model alkyne (phenyl acetylene) to give substituted pyridine products. Fundamental reactivity and selectivity studies are complemented by the synthesis of the polycyclic ergot alkaloid natural product xylanigripone A.

SUBMITTER: Thompson LC 

PROVIDER: S-EPMC11629385 | biostudies-literature | 2024 Dec

REPOSITORIES: biostudies-literature