Substituent-dependent synthesis of isomeric imidazoles from azirines and amidines

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-09-24 DOI:10.1016/j.tet.2025.134950

Ekaterina E. Galenko, Irina N. Prokop'eva, Alexander Yu. Ivanov, Timur O. Zanakhov, Mikhail S. Novikov, Alexander F. Khlebnikov

引用次数: 0

Abstract

The synthesis of 2,4,5-trisubstituted imidazoles with a Weinreb amide, ester, keto or aldehyde group, as well as 2,5-diaryl substituted imidazoles by the reaction of amidines with azirines has been reported. The reaction mechanism explaining dependence of imidazole structure on substituent at the position 2 of the azirine is discussed based on experiment with ¹⁵N-labelled azirine and DFT calculations.

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由氮嘧啶和脒合成咪唑异构体的取代基依赖性

用Weinreb酰胺、酯、酮或醛基合成2,4,5-三取代咪唑，以及用脒与氮嘧啶反应合成2,5-二芳基取代咪唑。通过15n标记的氮嘧啶实验和DFT计算，讨论了咪唑结构依赖于氮嘧啶2位取代基的反应机理。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.