K2S2O8-Initiated Cascade Cyclization of 2-Alkynylnitriles with Sodium Sulfinates: Access to Fused Cyclopenta[gh]phenanthridines

doi:10.6023/cjoc202007005

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (11): 3866-3872.DOI: 10.6023/cjoc202007005 Previous Articles Next Articles

Special Issue: 创刊四十周年专辑

过硫酸钾促进2-炔芳基腈与亚磺酸钠的自由基串联环化:构筑稠环环戊烯并[gh]菲啶

陈志超^a, 张红^b, 周树锋^a, 崔秀灵^b

a 华侨大学化工学院福建厦门 361021;
b 华侨大学生物医学学院分子药物教育部工程研究中心福建省分子医学重点实验室福建省高校精准医学与分子诊断重点实验室厦门市海洋与基因药物重点实验室福建厦门 361021

收稿日期:2020-07-01 修回日期:2020-07-30 发布日期:2020-08-11
通讯作者: 周树锋, 崔秀灵 E-mail:szhou@hqu.edu.cn;cuixl@hqu.edu.cn
基金资助:
国家自然科学基金（No.21572072）和高等学校学科创新引智计划（111计划，No.BC2018061）资助项目.

K₂S₂O₈-Initiated Cascade Cyclization of 2-Alkynylnitriles with Sodium Sulfinates: Access to Fused Cyclopenta[gh]phenanthridines

Chen Zhichao^a, Zhang Hong^b, Zhou Shufeng^a, Cui Xiuling^b

a College of Chemical Engineering, Huaqiao University, Xiamen, Fujian 361021;
b Engineering Research Center of Molecular Medicine, Ministry of Education, Key Laboratory of Fujian Molecular Medicine, Key Laboratory of Precision Medicine and Molecular Diagnosis of Fujian Universities, Key Laboratory of Xiamen Marine and Gene Drugs, School of Biomedical Sciences, Huaqiao University, Xiamen, Fujian 361021

Received:2020-07-01 Revised:2020-07-30 Published:2020-08-11
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21572072) and the Programme of Introducing Talents of Discipline to Universities (111 Project, No. BC 2018061).

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Abstract

A convenient K₂S₂O₈-initiated radical cascade cyclization for the construction of 4-sulfonated cyclopenta[gh]-phenanthridines from 2-alkynylnitriles and sodium sulfinates has been explored under metal-free conditions. This protocol features mild conditions, good functional group tolerance and broad substrate scope. A variety of potentially bioactive 4-sulfonated cyclopenta[gh]phenanthridines were facilely synthesized via direct annulation.

Key words: 2-alkynylnitriles, sodium sulfinate, 4-sulfonated cyclopenta[gh]phenanthridine, radical cyclization cascade

Cite this article

Chen Zhichao, Zhang Hong, Zhou Shufeng, Cui Xiuling. K₂S₂O₈-Initiated Cascade Cyclization of 2-Alkynylnitriles with Sodium Sulfinates: Access to Fused Cyclopenta[gh]phenanthridines[J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3866-3872.

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过硫酸钾促进2-炔芳基腈与亚磺酸钠的自由基串联环化:构筑稠环环戊烯并[gh]菲啶

K₂S₂O₈-Initiated Cascade Cyclization of 2-Alkynylnitriles with Sodium Sulfinates: Access to Fused Cyclopenta[gh]phenanthridines

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