Photoinduced Radical Annulations of Tetrahydroisoquinoline Derivatives with 2-Benzothiazolimines: Highly Diastereoselective Synthesis of Fused Hexahydroimidazo[2,1- a ]isoquinolines

作者：Bing Yi, Wenhui Zhang, Ziqi Yi, Fei Chen, Qianqian Zeng, Niannian Yi, Li Lv, Fan Zhang, Yanjun Xie, Jian‐Ping Tan · 发表于：The Journal of Organic Chemistry · 年份：2024 · DOI：10.1021/acs.joc.4c01691 · 被引用次数：6 · 研究领域：Catalytic C–H Functionalization Methods、Radical Photochemical Reactions、Synthesis and Catalytic Reactions

We report herein a photoinduced radical 1,3-dipolar cycloaddition between the 2-benzothiazolimines and tetrahydroisoquinoline derivatives with an organo-photocatalyst. A variety of benzothiazole-based hexahydroimidazo[2,1- a ]isoquinoline architectures with great synthetic value were conveniently and efficiently constructed in moderate to good yields and excellent diastereoselectivities with highly tolerant functional groups. Moreover, the practicality and utility of this protocol were demonstrated by scale-up synthesis and facile elaboration. Preliminary mechanistic investigations indicated that the reaction proceeded via a visible-light-induced radical 1,3-dipolar cycloaddition pathway. This finding is expected to stimulate a more extensive exploration of the green and concise synthesis of structurally diverse heterocyclic molecules in the synthetic community.