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原位生成的甲脒作为烯胺酮形成的碳/氮源:功能化4-酰基-1,2,3-三唑的一锅法合成

In Situ-Generated Formamidine as a Carbon/Nitrogen Source for Enaminone Formation: One-Pot Synthesis of Functionalized 4-Acyl-1,2,3-triazoles.

作者信息

Lin Jia-Xin, Chen You-Xin, Chien Min-Cheng, Chen Hsiang-Jou, Lai Chian-Hui, Liang Chien-Fu

机构信息

Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan.

Graduate Institute of Biomedical Engineering, National Chung Hsing University, Taichung 402, Taiwan.

出版信息

J Org Chem. 2024 Sep 6;89(17):12170-12175. doi: 10.1021/acs.joc.4c01054. Epub 2024 Aug 18.

Abstract

,-Dimethylformamide was reacted with hexamethyldisilazane to generate an ,-dimethylformimidamide intermediate; thereafter, a reaction with acetophenones/β-diketones was induced to form enaminones. The one-pot synthetic protocol described in this paper can be applied to synthesize 1,4-disubstituted 1,2,3-triazoles and 1,4,5-trisubstituted 1,2,3-triazoles, in which organic azides are used as substrates under optimized conditions. Furthermore, this protocol uses readily available materials, is nearly free of solvent, can be applied to gram-scale operations, and leads to the formation of structurally diverse products with favorable yields.

摘要

N,N-二甲基甲酰胺与六甲基二硅氮烷反应生成N,N-二甲基甲脒中间体;此后,引发其与苯乙酮/β-二酮反应以形成烯胺酮。本文所述的一锅法合成方案可应用于合成1,4-二取代的1,2,3-三唑和1,4,5-三取代的1,2,3-三唑,其中在优化条件下使用有机叠氮化物作为底物。此外,该方案使用易得的材料,几乎无溶剂,可应用于克级操作,并能以良好的产率形成结构多样的产物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6ef9/11382154/4edf294f5277/jo4c01054_0001.jpg

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