One-Step and Mild Synthesis of 3-(1,3,4-Oxadiazol-2-Yl)isoindolin-1-Ones Through Ugi Four-Component Domino Dicyclization,Asian Journal of Organic Chemistry

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One-Step and Mild Synthesis of 3-(1,3,4-Oxadiazol-2-Yl)isoindolin-1-Ones Through Ugi Four-Component Domino Dicyclization
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2024-04-23 , DOI: 10.1002/ajoc.202400036
Mei Sun ₁ , Chong-Yang Zeng ₂ , En-Shen Zhang ₂ , Qiang Zhang ₂ , Kai Chen ₂ , Yu-Gu Xu ₂ , Mei-Xia Fan ₂ , Meng-Ru He ₂ , Jing-Hui Shi ₂ , Ming-Wu Ding ₃

Affiliation

A novel and efficient Ugi four-component domino dicyclization strategy has been developed for one-step constructing diverse 3-(1,3,4-oxadiazol-2-yl)isoindolin-1-ones with good yields, without the need for additional additives. This domino dicyclization process underwent three consecutive reactions including Ugi, aza-Wittig and N-acylation by utilizing (N-isocyanimine)triphenylphosphorane, methyl 2-formylbenzoate, primary amines, and carboxylic acids. The initial biological activity testing revealed that compound 5 i exhibited good antifungal activity against certain fungi and demonstrated versatile applications in the fields of pesticide chemistry.

中文翻译：

Ugi四组分多米诺二环化一步温和合成3-(1,3,4-恶二唑-2-Yl)异吲哚啉-1-酮

开发了一种新颖高效的 Ugi 四组分多米诺二环化策略，可一步构建多种 3-(1,3,4-恶二唑-2-基)异吲哚啉-1-酮，且产率良好，无需额外添加剂。该多米诺二环化过程经历了三个连续反应，包括Ugi、氮杂维蒂希和利用(N-异氰胺)三苯基正膦、2-甲酰基苯甲酸甲酯、伯胺和羧酸的N-酰化反应。初步的生物活性测试表明，化合物5 i对某些真菌表现出良好的抗真菌活性，并在农药化学领域表现出广泛的应用。

更新日期：2024-04-23

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