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R3P/ICH2CH2I-Promoted Skeletal Editing of Cyclic Ethers via O/N Exchange
Yue Zhang1,2, Jin-Hong Lin1,2, Ji-Chang Xiao2
1Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, China.
Abstract:
The functionalization of cyclic ethers has received significant attention; however, the skeletal editing of cyclic ethers via O-to-N exchange remains challenging. Herein, we report a R3P/ICH2CH2I-promoted O-to-N exchange of cyclic ethers. This strategy enables the direct conversion of widely available cyclic ethers─such as tetrahydrofuran and 1,4-dioxane─into nitrogen-containing heterocycles, structural motifs commonly found in biologically active molecules. The method exhibits broad compatibility with secondary and tertiary amines, delivering the corresponding products in moderate to good yields.
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Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
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In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
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Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
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Based on their attached substituent...
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