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

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

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Pages (from-to)1023-1028
Number of pages6
JournalRussian Journal of Organic Chemistry
Volume56
Issue number6
DOIs
Publication statusPublished - 1 Jun 2020

Keywords

  • aminopyridines
  • diazotization
  • N,N-dimethylaminopyridines
  • pyridyl trifluoromethanesulfonates

ASJC Scopus subject areas

  • Organic Chemistry

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