恶唑酮与卤代炔前体的环加成/环反转反应生成的卤代吡啶衍生物
Halogenated Pyridine Derivatives from Cycloaddition / Cycloreversion of Oxazinone and Haloalkyne Precursors.
作者信息
Davis Elizabeth A, Hammett Megan S, Scheerer Jonathan R
机构信息
Department of Chemistry, William & Mary, P.O. Box 8795, Williamsburg, Virginia 23187, United States.
出版信息
Tetrahedron Lett. 2025 Oct 30;170. doi: 10.1016/j.tetlet.2025.155765. Epub 2025 Aug 5.
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.
摘要
本研究探索了1,4-恶嗪酮底物与卤代炔2π反应组分的合并环加成/环反转反应。卤代炔在狄尔斯-阿尔德反应中通常表现良好，与使用衍生的末端炔烃前体的反应序列相比，对反应序列的区域选择性影响较小。在串联环反转和消除CO之后，与3-卤代异构体变体相比，卤代炔对4-卤代吡啶产物的形成表现出适度的偏好。
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