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使用γ-氧化铝和超临界二氧化碳对氨基醇进行连续烷基化反应:与二氧化碳反应意外生成环状脲和聚氨酯。

Continuous -alkylation reactions of amino alcohols using γ-AlO and supercritical CO: unexpected formation of cyclic ureas and urethanes by reaction with CO.

作者信息

Streng Emilia S, Lee Darren S, George Michael W, Poliakoff Martyn

机构信息

School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.

School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK; Department of Chemical and Environmental Engineering, University of Nottingham Ningbo China, 199 Taikang East Road, Ningbo 315100, China.

出版信息

Beilstein J Org Chem. 2017 Feb 21;13:329-337. doi: 10.3762/bjoc.13.36. eCollection 2017.

DOI:10.3762/bjoc.13.36
PMID:28326142
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5331277/
Abstract

The use of γ-AlO as a heterogeneous catalyst in scCO has been successfully applied to the amination of alcohols for the synthesis of -alkylated heterocycles. The optimal reaction conditions (temperature and substrate flow rate) were determined using an automated self-optimising reactor, resulting in moderate to high yields of the target products. Carrying out the reaction in scCO was shown to be beneficial, as higher yields were obtained in the presence of CO than in its absence. A surprising discovery is that, in addition to cyclic amines, cyclic ureas and urethanes could be synthesised by incorporation of CO from the supercritical solvent into the product.

摘要

γ-氧化铝作为一种非均相催化剂在超临界二氧化碳中的应用已成功用于醇的胺化反应以合成N-烷基化杂环化合物。使用自动自优化反应器确定了最佳反应条件(温度和底物流速),得到了中等到高收率的目标产物。结果表明在超临界二氧化碳中进行反应是有益的,因为在有二氧化碳存在时比没有二氧化碳时能获得更高的收率。一个惊人的发现是,除了环状胺之外,通过将超临界溶剂中的二氧化碳引入产物中还可以合成环状脲和聚氨酯。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e492/5331277/9b662e821e66/Beilstein_J_Org_Chem-13-329-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e492/5331277/89ba1a8f77e4/Beilstein_J_Org_Chem-13-329-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e492/5331277/02ef4ed9e268/Beilstein_J_Org_Chem-13-329-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e492/5331277/2507096b49fb/Beilstein_J_Org_Chem-13-329-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e492/5331277/e1567c5c5928/Beilstein_J_Org_Chem-13-329-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e492/5331277/e354cda98731/Beilstein_J_Org_Chem-13-329-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e492/5331277/78b192f65463/Beilstein_J_Org_Chem-13-329-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e492/5331277/9b662e821e66/Beilstein_J_Org_Chem-13-329-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e492/5331277/89ba1a8f77e4/Beilstein_J_Org_Chem-13-329-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e492/5331277/02ef4ed9e268/Beilstein_J_Org_Chem-13-329-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e492/5331277/2507096b49fb/Beilstein_J_Org_Chem-13-329-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e492/5331277/e1567c5c5928/Beilstein_J_Org_Chem-13-329-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e492/5331277/e354cda98731/Beilstein_J_Org_Chem-13-329-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e492/5331277/78b192f65463/Beilstein_J_Org_Chem-13-329-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e492/5331277/9b662e821e66/Beilstein_J_Org_Chem-13-329-g004.jpg

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