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Introduction of Ether Groups onto Electron‐Deficient Nitrogen‐Containing Heteroaromatics Using Radical Chemistry under Transition‐Metal‐Free Conditions

Publisher: John Wiley & Sons Inc

E-ISSN: 1099-0690|2015|22|4973-4981

ISSN: 1434-193x

Source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Vol.2015, Iss.22, 2015-08, pp. : 4973-4981

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Abstract

AbstractElectron‐deficient nitrogen‐containing heteroaromatics, such as quinoline, isoquinoline, and pyridine, were treated with benzoyl peroxide in dioxane, tetrahydropyran, tetrahydrofuran, diethyl ether, and dipropyl ether at 80 °C to form alkylated nitrogen‐containing heteroaromatics in good yields under transition‐metal‐free conditions. This method was successfully applied to the preparation of lariat aza‐crown ethers using 18‐crown‐6 or 15‐crown‐5 with quinoline and isoquinoline in the presence of benzoyl peroxide in good yields under irradiation conditions with a Hg lamp.