Inverse Electron Demand Diels–Alder Reactions of 1,2,3-Triazines: Pronounced Substituent Effects on Reactivity and Cycloaddition Scope
作者:Erin D. Anderson、Dale L. Boger
DOI:10.1021/ja204856a
日期:2011.8.10
A systematic study of the inverse electron demand Diels-Alder reactions of 1,2,3-triazines is disclosed, including an examination of the impact of a C5 substituent. Such substituents were found to exhibit a remarkable impact on the cycloaddition reactivity of the 1,2,3-triazine without altering, and perhaps even enhancing, the intrinsic cycloaddition regioselectivity. The study revealed not only that
公开了对 1,2,3-三嗪的逆电子需求 Diels-Alder 反应的系统研究,包括对 C5 取代基影响的检查。发现此类取代基对 1,2,3-三嗪的环加成反应性表现出显着影响,而不会改变甚至可能增强固有的环加成区域选择性。该研究表明,反应性不仅可以通过 C5 取代基(R = CO(2)Me > Ph > H)可预测地调节,而且其影响对于转化 1,2,3-三嗪 (1)及其适度的环加成范围进入杂环氮杂二烯体系,其反应范围预示着广泛的合成效用,扩大了参与亲二烯体的范围。值得注意的是,这些研究定义了现在强大的附加杂环氮杂二烯,