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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

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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.

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Funding

This study was performed under financial support by the Ministry of Science and Higher Education of the Russian Federation (project no. Nauka FSWW-2020-0011).

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Authors and Affiliations

  1. National Research Tomsk Polytechnic University, 634050, Tomsk, Russia

    A. N. Sanzhiev, M. I. Potapova, E. A. Krasnokutskaya & V. D. Filimonov

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  1. A. N. Sanzhiev
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  2. M. I. Potapova
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  3. E. A. Krasnokutskaya
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  4. V. D. Filimonov
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Correspondence to E. A. Krasnokutskaya.

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Sanzhiev, A.N., Potapova, M.I., Krasnokutskaya, E.A. et al. A Novel One-Pot Synthesis of N,N-Dimethylaminopyridines by Diazotization of Aminopyridines in Dimethylformamide in the Presence of Trifluoromethanesulfonic Acid. Russ J Org Chem 56, 1023–1028 (2020). https://doi.org/10.1134/S1070428020060093

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