A microwave-assisted nucleophilic substitution reaction on a quinoline system: the synthesis of amino analogues of nitroxoline

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• 作者：Bogdan &Scaron ; tefane^a ; ^b ; Franc Po啪gan^a ; ^b ; ^{franc.pozgan@fkkt.uni-lj.si} ; Izidor Sosi膷^c ; Stanislav Gobec^c
• 关键词：Quinolines ; Nitroxoline ; Cyanomethoxy group ; Nucleophilic aromatic substitution ; Microwave-assisted synthesis
• 刊名：Tetrahedron Letters
• 出版年：2012
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：11 April, 2012
• 卷：53
• 期：15
• 页码：1964-1967
• 文件大小：1079 K

摘要

A reliable protocol for the synthesis of a series of 8-amino analogues of pharmacologically interesting nitroxoline (5-nitro-8-hydroxyquinoline) is described. The unprecedented displacement of the cyanomethoxy group of an O-cyanomethylated quinoline derivative by various primary and secondary amines selectively affords 5-nitroquinolin-8-ylamines in moderate-to-high yields. The reactions were accelerated significantly under microwave conditions in comparison with conventional heating.