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苯并咪唑叶立德与炔烃的环加成反应：新的机理见解

The Cycloaddition of the Benzimidazolium Ylides with Alkynes: New Mechanistic Insights.

作者信息

Moldoveanu Costel, Zbancioc Gheorghita, Mantu Dorina, Maftei Dan, Mangalagiu Ionel

机构信息

Department of Chemistry, Alexandru Ioan Cuza University of Iasi, Iasi, Romania.

出版信息

PLoS One. 2016 May 25;11(5):e0156129. doi: 10.1371/journal.pone.0156129. eCollection 2016.

DOI:10.1371/journal.pone.0156129
PMID:27224656
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4880325/
Abstract

New insights concerning the reaction mechanism in the cycloaddition reaction of benzimidazolium ylides to activated alkynes are presented. The proposed pathway leading both to 2-(1H-pyrrol-1-yl)anilines and to pyrrolo[1,2-a]quinoxalin-4(5H)-ones involves an opening of the imidazole ring from the cycloaddition product, followed by a nucleophilic attack of the aminic nitrogen to a proximal carbonyl group and the elimination of a leaving group. The mechanistic considerations are fully supported by experimental data, including the XRD resolved structure of the key reaction intermediate.

摘要

本文提出了关于苯并咪唑叶立德与活性炔烃环加成反应机理的新见解。所提出的生成2-(1H-吡咯-1-基)苯胺和吡咯并[1,2-a]喹喔啉-4(5H)-酮的途径涉及环加成产物中咪唑环的开环，随后氨基氮对近端羰基进行亲核进攻并消除一个离去基团。机理方面的考虑得到了实验数据的充分支持，包括关键反应中间体的X射线衍射解析结构。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f662/4880325/12a33a87dcec/pone.0156129.g006.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f662/4880325/94a59d5574ba/pone.0156129.g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f662/4880325/8d7c6701dd89/pone.0156129.g003.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f662/4880325/f7a8d7663d9e/pone.0156129.g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f662/4880325/12a33a87dcec/pone.0156129.g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f662/4880325/e0a1d688573d/pone.0156129.g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f662/4880325/94a59d5574ba/pone.0156129.g002.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f662/4880325/12a33a87dcec/pone.0156129.g006.jpg

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本文引用的文献

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New highlights of the syntheses of pyrrolo[1,2-a]quinoxalin-4-ones.吡咯并[1,2-a]喹喔啉-4-酮合成的新亮点。
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Microwave assisted reactions of some azaheterocylic compounds.一些氮杂环化合物的微波辅助反应。
超声辅助合成杂化喹啉-咪唑衍生物：一种绿色合成方法。
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Fluorescent Azasteroids through Ultrasound Assisted Cycloaddition Reactions.超声辅助环加成反应制备荧光氮杂薁
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