Synthesis of 5-(trifluoroacetyl)imidazoles from Bromoenones and Benzimidamides via Aza-Michael Initiated Ring Closure Reaction.

IF 1.7 4区化学 Q3 CHEMISTRY, ORGANIC

Current organic synthesis Pub Date : 2024-01-01 DOI:10.2174/1570179420666230420100643

Alexey R Romanov, Evgeniy V Kondrashov, Sergey V Zinchenko

引用次数: 0

Abstract

Introduction: A simple method for the preparation of 5-(trifluoroacetyl)imidazoles was elaborated.

Methods: The reaction of trifluoromethyl(α-bromoalkenyl)ketones with benzimidamides was employed to afford the target heterocycles in good yields.

Results: The assembly of imidazole core proceeds via aza-Michael adduct formation followed by intramolecular nucleophilic substitution and spontaneous aromatization as an oxidation sequence.

Conclusion: The yields of target imidazoles can be improved by the use of soft oxidizing agents.

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Aza-Michael引发环闭合反应合成5-(三氟乙酰基)咪唑。

介绍了一种制备5-(三氟乙酰基)咪唑的简便方法。方法:采用三氟甲基(α-溴烯基)酮与苯并咪达胺反应，得到收率较高的目标杂环。结果:咪唑核的组装是通过aza-Michael加合物的形成、分子内亲核取代和自发芳构化的氧化过程进行的。结论:使用软氧化剂可提高目标咪唑的收率。

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

Current organic synthesis 化学-有机化学

CiteScore

3.40

自引率

5.60%

发文量

审稿时长

6-12 weeks

期刊介绍： Current Organic Synthesis publishes in-depth reviews, original research articles and letter/short communications on all areas of synthetic organic chemistry i.e. asymmetric synthesis, organometallic chemistry, novel synthetic approaches to complex organic molecules, carbohydrates, polymers, protein chemistry, DNA chemistry, supramolecular chemistry, molecular recognition and new synthetic methods in organic chemistry. The frontier reviews provide the current state of knowledge in these fields and are written by experts who are internationally known for their eminent research contributions. The journal is essential reading to all synthetic organic chemists. Current Organic Synthesis should prove to be of great interest to synthetic chemists in academia and industry who wish to keep abreast with recent developments in key fields of organic synthesis.