自由基引发级联环化反应高效合成吡咯[1,2-a]吲哚-3- 1。

IF 2.7 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2025-04-16 DOI:10.1039/d5ob00474h

Han Zhang , Yuze Lin , Gang Yang , Xifa Yang , Xiuling Cui

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引用次数: 0

摘要

研究了2,2′-偶氮（2-甲基丙腈）（AIBN）与1-甲基丙烯酰-3-苯基- 1h -吲哚-2-碳腈自由基级联氰基异丙基/环化反应，为获得各种吡咯[1,2- A]吲哚-3- 1提供了一种高效的策略，收率高，官能团相容性好。该方案的显著特点包括避免使用光催化剂和过渡金属，可扩展性和乙醇作为绿色溶剂。此外，还进行了机理研究，并提出了一个合理的机制。

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Efficient synthesis of pyrrolo[1,2-a]indol-3-ones through a radical-initiated cascade cyclization reaction†

A radical cascade cyanoisopropylation/cyclization reaction of 2,2′-azobis(2-methylpropionitrile) (AIBN) with 1-methacryloyl-3-phenyl-1H-indole-2-carbonitrile has been realized, providing an efficient strategy to access various pyrrolo[1,2-a]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.

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来源期刊

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.