Three‐Component Synthesis of Substituted Azepines by Gold/Magnesium Orthogonal‐Relay Catalysis

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-11-19 DOI:10.1002/adsc.202400940

Shuto Kosuge , Yoshihiro Kiraku , Kiyoshi Tsuge , Kenji Sugimoto , Yuji Matsuya

引用次数: 0

Abstract

A three‐component one‐pot synthesis of substituted azepines was realized by gold/magnesium orthogonal relay catalysis. The one‐pot synthesis involves simply mixing and heating propiolates, imines, and activated cyclopropanes to initiate a gold‐catalyzed aza‐enyne metathesis between propiolates and imines, followed by a magnesium‐catalyzed [4+3] cycloaddition reaction of the resultant 1‐azabutadienes and the cyclopropanes, yielding substituted azepines. The substituted azepines including 22 derivatives could be successfully prepared in good to excellent yield (61–95%). The reaction was also conducted on one‐gram scale.

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金/镁正交延迟催化三组分合成取代的氮杂环庚烷

通过金/镁正交中继催化，实现了取代氮杂庚烯的三组分单锅合成。该一锅合成法只需简单地混合并加热丙炔盐、亚胺和活化环丙烷，即可在丙炔盐和亚胺之间启动金催化的氮杂烯炔偏析反应，然后在镁催化下对生成的 1-氮杂丁二烯和环丙烷进行[4+3]环加成反应，从而得到取代的氮杂环庚烷。包括 22 种衍生物在内的相应取代氮杂环庚烷可以成功制备，收率从良好到极佳（61-95%）。该反应可在一克规模下进行。

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.