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膦催化α-琥珀酰亚胺取代的联烯酸酯与醌甲基化物的γ'-碳1,6-共轭加成反应:4-二芳基甲基化3,4-二取代马来酰亚胺的合成

Phosphine-Catalyzed γ'-Carbon 1,6-Conjugate Addition of α-Succinimide Substituted Allenoates with -Quinone Methides: Synthesis of 4-Diarylmethylated 3,4-Disubstituted Maleimides.

作者信息

Gao Zhenzhen, Zhou Xiaoming, Liu Dandan, Nie Baoshen, Lu Hanchong, Chen Xiaotong, Wu Jiahui, Li Lei, Wang Xuekun

机构信息

State Key Laboratory for Macromolecule Drugs and Large-Scale Manufacturing, School of Pharmaceutical Sciences, Liaocheng University, Liaocheng 252059, China.

出版信息

Molecules. 2024 May 31;29(11):2593. doi: 10.3390/molecules29112593.

DOI:10.3390/molecules29112593
PMID:38893468
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11173458/
Abstract

In this paper, an interesting γ'-carbon 1,6-conjugate addition for phosphine-catalyzed α-succinimide substituted allenoates has been disclosed. A wide array of substrates was found to participate in the reaction, resulting in the production of diverse 4-diarylmethylated 3,4-disubstituted maleimides with satisfactory to outstanding yields. Furthermore, a plausible mechanism for the reaction was proposed by the investigators.

摘要

本文报道了一种有趣的膦催化α-琥珀酰亚胺取代的联烯酸酯的γ'-碳1,6-共轭加成反应。发现多种底物可参与该反应,以令人满意至优异的产率生成各种4-二芳基甲基化的3,4-二取代马来酰亚胺。此外,研究人员还提出了该反应可能的机理。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ee/11173458/c1b4fb5579d1/molecules-29-02593-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ee/11173458/5b55a0052362/molecules-29-02593-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ee/11173458/5285e5c1a96e/molecules-29-02593-sch002a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ee/11173458/e242fe9a5780/molecules-29-02593-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ee/11173458/f61199026bed/molecules-29-02593-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ee/11173458/c1b4fb5579d1/molecules-29-02593-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ee/11173458/5b55a0052362/molecules-29-02593-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ee/11173458/5285e5c1a96e/molecules-29-02593-sch002a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ee/11173458/e242fe9a5780/molecules-29-02593-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ee/11173458/f61199026bed/molecules-29-02593-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ee/11173458/c1b4fb5579d1/molecules-29-02593-sch005.jpg

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本文引用的文献

1
Phosphine-Catalyzed (4 + 2) Annulation of Allenoates Bearing Acidic Hydrogen with 1,1-Dicyanoalkenes.膦催化含酸性氢的联烯酸酯与1,1-二氰基烯烃的(4 + 2)环化反应
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Iron(III)-catalyzed tandem annulation of indolyl-substituted -quinone methides with ynamides for the synthesis of cyclopenta[]indoles.铁(III)催化吲哚取代的 -醌甲川与炔酰胺的串联环化反应合成环戊[]吲哚。
Chem Commun (Camb). 2022 Aug 2;58(62):8710-8713. doi: 10.1039/d2cc03252j.
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Phosphine-Catalyzed (4 + 2) Annulation of Allenoates with Benzofuran-Derived Azadienes and Subsequent Thio-Michael Addition.
膦催化的丙二烯酸酯与苯并呋喃衍生的偶氮二烯的(4 + 2)环加成反应和随后的硫迈克尔加成反应。
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Metal-Free, Acid-Catalyzed 1,6-Conjugate Addition of NH-Sulfoximines to -Quinone Methides: Accessing to Diarylmethine Imino Sulfanone.无金属、酸催化的 NH-亚磺酰胺与-醌甲醚的 1,6-共轭加成:获得二芳基甲撑亚氨基磺酮。
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Phosphine-Catalyzed Intermolecular Dienylation of Alkynoate with -Quinone Methides.膦催化炔酸酯与 -醌甲醚的分子间二烯化反应。
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Phosphorus-Based Catalysis.基于磷的催化作用
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Bis(amino)cyclopropenium Ion as a Hydrogen-Bond Donor Catalyst for 1,6-Conjugate Addition Reactions.双(氨基)环丙烯鎓离子作为1,6-共轭加成反应的氢键供体催化剂
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