Department of Chemistry, The University of Texas at San Antonio, San Antonio, Texas 78249, United States.
Org Lett. 2021 Aug 20;23(16):6542-6546. doi: 10.1021/acs.orglett.1c02352. Epub 2021 Aug 9.
1,2,3-Triazine 1-oxides are formed by nitrosyl addition from -butyl nitrite to the vinylogous position of vinyl diazo compounds. This transformation, which is a formal intermolecular [5 + 1] cycloaddition, occurs under mild conditions, with high functional group tolerance and regioselectivity, and can be employed for late-stage functionalization. Upon heating at refluxing chlorobenzene temperature, these triazine--oxides undergo dinitrogen extrusion to form isoxazoles in very high yields.
1,2,3-三嗪 1-氧化物是由 -丁基亚硝酰化合物通过亚硝酰基加成到乙烯基重氮化合物的烯丙位形成的。这种转化是一种形式上的分子间[5+1]环加成反应，在温和的条件下进行，具有高官能团容忍度和区域选择性，可以用于后期的功能化。在回流氯苯温度下加热时，这些三嗪-氧化物会通过释放氮气形成异恶唑，产率非常高。
