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钯催化由酰肼基氯化物和NaN进行的1,2,4-三唑-3-酮的羰基化串联合成

Palladium-Catalyzed Cascade Carbonylative Synthesis of 1,2,4-Triazol-3-ones from Hydrazonoyl Chlorides and NaN.

作者信息

Du Shiying, Wang Wei-Feng, Song Yufei, Chen Zhengkai, Wu Xiao-Feng

机构信息

Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. China.

Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Straβe 29a, 18059 Rostock, Germany.

出版信息

Org Lett. 2021 Feb 5;23(3):974-978. doi: 10.1021/acs.orglett.0c04167. Epub 2021 Jan 12.

Abstract

A palladium-catalyzed three-component carbonylative reaction for the synthesis of 3-1,2,4-triazol-3-ones from hydrazonoyl chlorides and NaN has been achieved. The reaction presumably proceeds through a cascade carbonylation, acyl azide formation, Curtius rearrangement, and intramolecular nucleophilic addition sequence. A wide variety of structurally diverse 3-1,2,4-triazol-3-ones were constructed in moderate to excellent yields. Benzene-1,3,5-triyl triformate (TFBen) was applied as a solid and convenient CO surrogate.

摘要

实现了一种钯催化的三组分羰基化反应,用于从酰肼基氯化物和NaN合成3-1,2,4-三唑-3-酮。该反应可能通过级联羰基化、酰基叠氮形成、库尔提斯重排和分子内亲核加成序列进行。以中等至优异的产率构建了各种结构多样的3-1,2,4-三唑-3-酮。苯-1,3,5-三基三甲酸酯(TFBen)被用作一种固体且方便的CO替代物。

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