以1,3-偶极环加成[60]富勒烯与原位生成的亚甲基酰基化合物合成环氧亚胺桥接富勒烯-融合四氢氮卓类化合物。

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-20 Epub Date: 2025-06-09 DOI:10.1021/acs.orglett.5c01756

Zheng-Dong Yang, Ping Wu, Fa-Bao Li, Cheng Zhou, Si-Min Zhao, Shu-Wan Bai, Wangqiang Shen, Li Liu

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引用次数: 0

摘要

在N-（3-溴丙基）邻苯二胺存在下，以Pb2(OAc)2(OH)2和（CH3）3COK为原料，以[60]富勒烯和伯胺为原料，一步反应合成了一系列独特的ep亚胺桥接富勒烯-融合四氢氮卓衍生物，收率中高。目前通过1,3-偶极环加成策略制备环氧亚胺桥接富勒烯双环化合物的方案以前从未报道过。基于控制实验和密度泛函理论（DFT）计算，提出了一种可能的反应机理来解释所得产物的生成。

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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Synthesis of Epimino-Bridged Fullerene-Fused Tetrahydroazepines via 1,3-Dipolar Cycloaddition of [60]Fullerene with in Situ Generated Azomethine Ylides.

A series of unique epimino-bridged fullerene-fused tetrahydroazepine derivatives were synthesized in moderate to good yields by the simple one-step reaction of [60]fullerene with primary amines in the presence of N-(3-bromopropyl)phthalimide with the addition of Pb₂(OAc)₂(OH)₂ and (CH₃)₃COK. The current protocol for the preparation of epimino-bridged fullerene bicyclic compounds via the 1,3-dipolar cycloaddition strategy has never been reported previously. A possible reaction mechanism is proposed to elucidate the generation of the obtained products based on control experiments and density functional theory (DFT) calculations.

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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.