银催化叠氮醚与3-氨基丙烯酸酯开环和C-H胺化的正[3 + 3]杂环反应：得到1,4,5,6-四氢吡嗪

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-17 DOI:10.1021/acs.orglett.5c0095210.1021/acs.orglett.5c00952

Ming-Zhu Zhang, Liang Zeng, Ming Hu*, Fu-Jin Sun* and Jin-Heng Li*,

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引用次数: 0

摘要

直接构建具有多种功能的哌嗪支架仍然是重要但具有挑战性的。本文报道了通过开环和乙烯基C(sp2) -H胺化，银催化的aziridine与3-氨基丙烯酸酯的正式[3 + 3]杂环反应，直接合成了四取代的1,4,5,6-四氢吡嗪。该方案在催化活化银Lewis酸后，通过选择性亲核开环和C-H胺化级联形成两个新的C-N键，具有底物范围广、官能团耐受性好、选择性优异的特点。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Silver-Catalyzed Formal [3 + 3] Heteroannulation of Aziridines with 3-Aminoacrylates via Ring-Opening and C–H Amination: Access to 1,4,5,6-Tetrahydropyrazines

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Silver-Catalyzed Formal [3 + 3] Heteroannulation of Aziridines with 3-Aminoacrylates via Ring-Opening and C–H Amination: Access to 1,4,5,6-Tetrahydropyrazines

Direct construction of the piperazine scaffolds with multiple functionalities remains important yet challenging. Herein, a silver-catalyzed formal [3 + 3] heteroannulation of aziridines with 3-aminoacrylates via ring-opening and vinyl C(sp²)–H amination for the direct synthesis of tetrasubstituted 1,4,5,6-tetrahydropyrazines is reported. Upon the catalytic activation of the silver Lewis acid, this protocol enables the formation of two new C–N bonds through selective nucleophilic ring-opening and C–H aminative cyclization cascades, featuring a broad substrate scope and a good functional group tolerance with excellent selectivity.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.