Yashmin Sabina, Ali Rashid, Mondal Santa, Khan Abu Taleb
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati-781039, India.
Chem Commun (Camb). 2022 May 12;58(39):5853-5856. doi: 10.1039/d2cc01067d.
An unprecedented metal-free and catalyst-free synthesis of benzo[]chromeno[4,3,2-]phenanthridine derivatives, a class of 1,6-diheterophenalenoid heterocycle, is reported for the first time. The oxidative cross-coupling reaction for the remote cyclization is achieved through the generated -quinone methide intermediate followed by an electrocyclic ring closure reaction. The aromatization of the cyclohexane ring is achieved by sequential H shift, hydroxylation, and elimination reaction. DMSO-assisted concomitant cyclization and aromatization reactions are also disclosed for the first time.
首次报道了一类1,6-二杂菲并类杂环化合物——苯并[]色烯并[4,3,2-]菲啶衍生物的前所未有的无金属、无催化剂合成方法。远程环化的氧化交叉偶联反应通过生成的醌甲基化物中间体实现，随后进行电环化闭环反应。环己烷环的芳构化通过依次的氢迁移、羟基化和消除反应实现。首次还公开了二甲基亚砜辅助的伴随环化和芳构化反应。
