Xu Rong-Yao, Liu Xiu, Sun Guang, Zhang Zhi-Yuan, Dong Ming, Zhao Liya, Zhang Si-Miao, Wang Xi-Yang, Zhang Hong-Xu, Yang Shang-Jie, Wang Xiuguang, Li Bin, Li Jian, Li Chunju
Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University Tianjin 300387 P. R. China
School of Chemistry and Chemical Engineering, Henan Normal University P. R. China.
RSC Adv. 2023 Oct 24;13(43):30269-30272. doi: 10.1039/d3ra05671f. eCollection 2023 Oct 11.
Reported here is the efficient macrocyclization facilitated by skeleton preorganization. A pyridylcarbazole macrocycle and a phenylpyridylcarbazole macrocycle was synthesized in yield up to 75%. Single-crystal structures and theoretic computation uncovered that the skeleton preorganization promoted the formation of cyclization-favorable conformation of noncyclic precursors π⋯π interactions. This result provided a new approach for the efficient syntheses of macrocycles.
本文报道了由骨架预组织促进的高效大环化反应。合成了吡啶基咔唑大环和苯基吡啶基咔唑大环,产率高达75%。单晶结构和理论计算表明,骨架预组织促进了非环状前体形成有利于环化的构象以及π⋯π相互作用。该结果为大环化合物的高效合成提供了一种新方法。