通过亲核/重排/叠氮-烯级联反应无金属合成 2-苄叉吲哚啉-3-酮

IF 1.7 4区化学 Q3 CHEMISTRY, ORGANIC Synlett Pub Date : 2024-06-10 DOI:10.1055/a-2341-9185

Quan Tang, Hua Wang, Tianyu Long, Han-Han Kong, Qing-Qing Yang, Nianyu Huang, Long Wang

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引用次数: 0

摘要

本研究开发了一种无金属合成 2-亚苄基吲哚啉-3-酮的方法，该方法是通过邻氮代苯甲醛和末端炔烃的形式化 [4+1] 环化反应合成 2-亚苄基吲哚啉-3-酮。该方法具有操作简单、反应条件温和、起始原料易得等特点。该方法制备了多种 2-亚苄基吲哚啉-3-酮，收率从中等到极佳。机理研究表明，该反应可通过亲核加成/重排/叠氮-烯环加成途径生成 2-亚苄基吲哚啉-3-酮。

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Metal-Free Synthesis of 2-Benzylideneindolin-3-ones via a Nucleophilic/Rearrangement/Azide-Alkene Cascade Reaction

A metal-free synthesis of 2-benzylideneindolin-3-ones via a formal [4+1] annulation reaction from o-azidobenzaldehydes and terminal alkynes has been developed. The method features operational simplicity, mild reaction conditions and ready availability of starting materials. A broad range of 2-benzylideneindolin-3-ones were prepared in moderate to excellent yields. Mechanism studies indicated that the reaction may proceed via a nucleophilic addition/rearrangement/azide-alkene cycloaddition pathway to produce 2-benzylideneindolin-3-ones.

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来源期刊

Synlett 化学-有机化学

CiteScore

3.40

自引率

5.00%

发文量

369

审稿时长

1 months

期刊介绍： SYNLETT is an international journal reporting research results and current trends in chemical synthesis in short personalized reviews and preliminary communications. It covers all fields of scientific endeavor that involve organic synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines and offers the possibility to publish scientific primary data.