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在水相和机械化学条件下，甲酰胺作为羰基前体用于催化合成Passerini加合物。

-Formamide as a carbonyl precursor in the catalytic synthesis of Passerini adducts under aqua and mechanochemical conditions.

作者信息

Salami Sodeeq Aderotimi, Smith Vincent J, Krause Rui W M

机构信息

Rhodes University Grahamstown Makhanda 6139 South Africa

出版信息

RSC Adv. 2023 Jan 27;13(6):4019-4031. doi: 10.1039/d2ra06189a. eCollection 2023 Jan 24.

DOI:10.1039/d2ra06189a
PMID:36756572
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9890950/
Abstract

A new simple, efficient, and environmentally friendly protocol is presented for the catalytic synthesis of α-acyloxycarboxamides using -formamides as a carbonyl precursor under aqua and mechanochemical conditions. Immobilized sulfuric acid on silica gel was employed for the synthesis of desired products, the reaction of benzoic acid, 1-napthylisocyanide and various heterocyclic -formamides. After a careful optimization of the reaction conditions, the desired Passerini products were obtained in high to excellent yields in short reaction times (10-30 min) at room temperature. The highly efficient and environmentally friendly method provides a facile access to a library of α-acyloxycarboxamides derivatives for future research on bioactivity screening.

摘要

本文介绍了一种新型的简单、高效且环保的方法，用于在水相和机械化学条件下，以甲酰胺作为羰基前体催化合成α-酰氧基羧酰胺。使用硅胶负载硫酸来合成所需产物，即苯甲酸、1-萘基异腈与各种杂环甲酰胺的反应。在仔细优化反应条件后，在室温下短反应时间（10 - 30分钟）内以高至优异的产率获得了所需的Passerini产物。这种高效且环保的方法为未来生物活性筛选研究提供了一种简便的途径来获取α-酰氧基羧酰胺衍生物库。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2568/9890950/b540564be46f/d2ra06189a-s6.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2568/9890950/e5e4851cbfda/d2ra06189a-s1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2568/9890950/b540564be46f/d2ra06189a-s6.jpg

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本文引用的文献

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2
Catalytic Performance of Immobilized Sulfuric Acid on Silica Gel for -Formylation of Amines with Triethyl Orthoformate.硅胶固载硫酸对三乙基原甲酸酯催化胺的 - 甲酰化反应的性能。
Molecules. 2022 Jun 30;27(13):4213. doi: 10.3390/molecules27134213.
3
Two decades of recent advances of Ugi reactions: synthetic and pharmaceutical applications.
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RSC Adv. 2020 Nov 23;10(70):42644-42681. doi: 10.1039/d0ra07501a.
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