Base‐Mediated Four‐Component Intramolecular Cyclization reaction: One‐pot Access to Imidazole‐4‐(2H)‐ones

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2025-01-22 DOI:10.1002/adsc.202401433

Ganesh Pawar, Indrajeet Barve, Li-Ching Shen, Chung-Ming SUN

引用次数: 0

Abstract

A base‐mediated one‐pot, two‐step, four‐component reaction has been developed to synthesize imidazole‐4(2H)‐ones, utilizing commercially available amino acid esters, aldehydes, alkynes, and amino alcohols. Control experiments and isolation of the intermediate revealed the mechanistic details. This four‐component reaction proceeds via imine formation, followed by the nucleophilic addition of alkyne to form a propargylamine precursor. Subsequently, the propargylamine precursor undergoes base‐mediated conversion into 1‐azadiene, followed by in situ ketene formation to generate (allyl‐dene‐amino)prop‐1‐en‐1‐one. The nucleophilic addition of amino alcohol and subsequent intramolecular cyclization provides imidazole‐4 (2H)‐ones exclusively.

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碱介导的四组分分子内环化反应：咪唑- 4 - (2H) -酮的一罐途径

利用市售的氨基酸酯、醛、炔和氨基醇，采用碱介导的一锅、两步、四组分反应合成咪唑- 4(2H) -酮。对照实验和分离中间体揭示了机理细节。这个四组分反应首先生成亚胺，然后是亲核炔的加成，形成丙胺前体。随后，丙基胺前体经过碱介导转化为1 -偶氮二烯，然后原位形成烯酮，生成（烯丙基-烯丙基-氨基）prop - 1 - en - 1 - one。氨基醇的亲核加成和随后的分子内环化只提供咪唑- 4 (2H) -酮。

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

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.