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Halogenated Pyridine Derivatives from Cycloaddition / Cycloreversion of Oxazinone and Haloalkyne Precursors. | LitMetric

Halogenated Pyridine Derivatives from Cycloaddition / Cycloreversion of Oxazinone and Haloalkyne Precursors.

Tetrahedron Lett

Department of Chemistry, William & Mary, P.O. Box 8795, Williamsburg, Virginia 23187, United States.

Published: October 2025


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Article Abstract

This study explores the merged cycloaddition/cycloreversion of 1,4-oxazinone substrates with haloalkyne 2π reaction components. Haloalkynes proved generally competent in the Diels-Alder operation and exerted a small influence on the regioselection of the reaction sequence as compared to the reaction sequence with the derived terminal alkyne precursors. Following tandem cycloreversion and elimination of CO, the haloalkynes showed a modest preference for formation of 4-halo pyridine products over 3-halo isomeric variants.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC12373122PMC
http://dx.doi.org/10.1016/j.tetlet.2025.155765DOI Listing

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