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Synthesis of arylsulfonyl-substituted indolo[2,1-a]isoquinolin-6(5H)-one derivatives via a TBAI-catalyzed radical cascade cyclization

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Chinese Chemical Letters 2022年第1期33卷 276-279页

作者： Shengxian Zhai Shuxian Qiu Shuai Yang Bingyan Hua Yongsheng Niu Chuchu Han Youzhu Yu Yuchao Li Hongbin Zhai College of Chemistry&Environmental Engineering Anyang Institute of TechnologyAnyang 455000China Department of Chemistry Guangdong University of EducationGuangzhou 510303China State Key Laboratory of Chemical Oncogenomics and Key Laboratory of Chemical Genomics Shenzhen Engineering Laboratory of Nano Drug Slow-ReleaseShenzhen Graduate School of Peking UniversityShenzhen 518055China

We have developed a metal-free radical cascade reaction of N-substituted 2-aryl indoles with readily available sulfonyl hydrazides for the rapid construction of arylsulfonyl-substituted indolo[2,1-a]isoquinolin-6(5H)-one derivatives.With the TBAI–TBHP catalytic system,a broad series of structurally diverse indolo[2,1-a]isoquinolin-6(5H)-one derivatives were obtained in moderate to excellent yields.The reaction features mild reaction conditions,operationally easiness,scaled-up feasibility,and high functional-group-tolerance.

关键词： TBAI-catalyzed Metal-free radical cascade Cyclization Nitrogen-containing heterocycles Fused-indole derivatives

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Alkyl radical Triggered in situ SO2-Capture cascades

Alkyl Radical Triggered in situ SO2-Capture Cascades

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中国化学会·第十五届全国有机合成化学学术研讨会

作者： Honggui Huang 李毅 Department of Chemistry Fuzhou University 福州大学

Sulfur dioxide(SO) could serve as the most direct and attractive feedstock to synthesize sulfonyl compounds which are of great importance on pharmaceuticals, agrochemicals, materials and synthetic intermediates. However, direct utilization of SO for the synthesis of value-added products was mainly restricted by its notorious toxicity, hard-to-handle gaseous state and amphoteric chemical characteristic;therefore reports on direct SO-involved chemistry in organic synthesis are relatively rare.As the ongoing work of our recent efforts on radical cascade reactions to construct compounds with multiple rings, we reported an unprecedented in situ SO-capture cascade triggered by alkyl radical(Fig.1-a). Mechanistic investigations suggest that, triggered by alkyl radical, SO was released in situ and subsequently fixed into polycyclic small molecules.Through this method, a wide range of alkylsulfonyl substituted polycyclic compounds were easily prepared with high yields and good functional group tolerability.Based on this strategy, we disclosed recently the construction of sulfonated oxindoles assembled by radical triggered in situ SO-capture cascade(Fig.1-b).

关键词： in situ SO2-capture radical cascade sulfonated oxindoles alkyl radical

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