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A Novel One-Pot Synthesis of N , N -Dimethylaminopyridines by Diazotization of Aminopyridines in Dimethylformamide in the Presence of Trifluoromethanesulfonic Acid
Russian Journal of Organic Chemistry ( IF 0.8 ) Pub Date : 2020-07-20 , DOI: 10.1134/s1070428020060093 A. N. Sanzhiev , M. I. Potapova , E. A. Krasnokutskaya , V. D. Filimonov
中文翻译:
在三氟甲磺酸存在下,通过氨基吡啶在二甲基甲酰胺中的重氮化反应,一锅法合成N,N-二甲基氨基吡啶
更新日期:2020-07-20
Russian Journal of Organic Chemistry ( IF 0.8 ) Pub Date : 2020-07-20 , DOI: 10.1134/s1070428020060093 A. N. Sanzhiev , M. I. Potapova , E. A. Krasnokutskaya , V. D. Filimonov
Abstract
Diazotization of aminopyridines in the presence of trifluoromethanesulfonic acid gives the corresponding pyridinyl trifluoromethanesulfonates instead of expected diazonium salts. Pyridinyl trifluoromethanesulfonates can be converted to N,N-dimethylaminopyridines on heating in dimethylformamide via replacement of the trifluoromethanesulfonyloxy group. The reaction is accelerated under microwave irradiation. A novel one-pot procedure has been proposed for the synthesis of 2- and 4-(dimethylamino)pyridines from commercially available aminopyridines. The procedure provides high yields of the target products, and it can be regarded as an alternative to the known methods of synthesis of N,N-dimethylpyridin-4-amine (DMAP) widely used as base catalyst in organic synthesis.中文翻译:
在三氟甲磺酸存在下,通过氨基吡啶在二甲基甲酰胺中的重氮化反应,一锅法合成N,N-二甲基氨基吡啶