A Novel One-Pot Synthesis of N,N-Dimethylaminopyridines by Diazotization of Aminopyridines in Dimethylformamide in the Presence of Trifluoromethanesulfonic Acid

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 vi...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2020-06, Vol.56 (6), p.1023-1028
Main Authors: Sanzhiev, A. N., Potapova, M. I., Krasnokutskaya, E. A., Filimonov, V. D.
Format: Article
Language:English
Subjects:
Chemical synthesis
Chemistry
Chemistry and Materials Science
Organic Chemistry
Pyridines
Triflic acid
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Summary: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.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428020060093