通过自由基引发的串联环化反应高效合成吡咯并[1,2-]吲哚-3-酮。
Efficient synthesis of pyrrolo[1,2-]indol-3-ones through a radical-initiated cascade cyclization reaction.
作者信息
Zhang Han, Lin Yuze, Yang Gang, Yang Xifa, Cui Xiuling
机构信息
Engineering Research Centre of Molecular Medicine of 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 361021, China.
College of Plant Protection, Henan Agricultural University, Zhengzhou, 450002, China.
出版信息
Org Biomol Chem. 2025 May 21;23(20):4966-4970. doi: 10.1039/d5ob00474h.
A radical cascade cyanoisopropylation/cyclization reaction of 2,2'-azobis(2-methylpropionitrile) (AIBN) with 1-methacryloyl-3-phenyl-1-indole-2-carbonitrile has been realized, providing an efficient strategy to access various pyrrolo[1,2-]indol-3-ones in good to excellent yields with good functional group compatibility. The notable features of this protocol include avoiding the use of a photocatalyst and a transition metal, scalability, and ethanol as the green solvent. Moreover, mechanistic studies have been conducted and a plausible mechanism has been proposed.
实现了2,2'-偶氮二(2-甲基丙腈)(AIBN)与1-甲基丙烯酰基-3-苯基-1-吲哚-2-腈的自由基串联氰基异丙基化/环化反应，为高效合成各种吡咯并[1,2-]吲哚-3-酮提供了一种策略，产率良好至优异，官能团兼容性良好。该方法的显著特点包括避免使用光催化剂和过渡金属、可扩展性以及使用乙醇作为绿色溶剂。此外，还进行了机理研究并提出了合理的机理。
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