Synthesis of Medium-Ring-Sized Benzolactams by Using Strong Electrophiles and Quantitative Evaluation of Ring-Size Dependency of the Cyclization Reaction Rate
Synthesis of Medium-Ring-Sized Benzolactams by Using Strong Electrophiles and Quantitative Evaluation of Ring-Size Dependency of the Cyclization Reaction Rate
复制标题
DOI：
10.1021/acs.joc.9b02843
复制
发表时间：
2020-01-17
影响因子：
3.6
通讯作者：
Ohwada, Tomohiko
中科院分区：
文献类型：
--
作者：
Kurouchi, Hiroaki;Ohwada, Tomohiko
通过氨基甲酰基阳离子（R1R2N+=C=O）的亲电芳香取代反应，不经稀释，以较高的产率合成了具有中等大小环的苯并内酰胺。这些反应被用来定量地检查与五元或六元环形成相比，中等大小的环形成的延迟程度。在25 ℃时，生成环苯并内酰胺的反应速率顺序为六元环>五元环>七元环>八元环>九元环。本反应提供了一条合成八元和九元苯并内酰胺的途径。
Benzolactams with medium-sized rings were synthesized via the electrophilic aromatic substitution reaction of carbamoyl cations (R1R2N+=C=O) in good to high yields without dilution. These reactions were utilized to quantitatively examine the extent of retardation of medium-sized ring formation, compared to five- or six-membered ring formation. The order of reaction rates of formation of cyclic benzolactams is six- > five- > seven- > eight- > nine-membered ring at 25 degrees C. The present reaction provides a route to eight- and nine-membered benzolactams.