Reaction of Picolinamides with Ketones Producing a New Type of Heterocyclic Salts With a 4-Imidazoline Ring

Eugene P Kramarova; Dmitry N. Lyahmun; Dmitry V. Tarasenko; Sophia S. Borisevich; Edward Khamitov; Alfia R. Yusupova; Alexander A. Korlyukov; Alexander R. Romanenko; Tatiana A. Shmigol; Sergey Yu. Bylikin; Yuri I. Baukov; Vadim V. Negrebetsky

doi:10.20944/preprints202311.0459.v1

A peer-reviewed article of this Preprint also exists.

Kramarova, E.P.; Lyakhmun, D.N.; Tarasenko, D.V.; Borisevich, S.S.; Khamitov, E.M.; Yusupova, A.R.; Korlyukov, A.A.; Romanenko, A.R.; Shmigol, T.A.; Bylikin, S.Y.; Baukov, Y.I.; Negrebetsky, V.V. Reaction of Picolinamides with Ketones Producing a New Type of Heterocyclic Salts with an Imidazolidin-4-One Ring. Molecules 2024, 29, 206. Kramarova, E.P.; Lyakhmun, D.N.; Tarasenko, D.V.; Borisevich, S.S.; Khamitov, E.M.; Yusupova, A.R.; Korlyukov, A.A.; Romanenko, A.R.; Shmigol, T.A.; Bylikin, S.Y.; Baukov, Y.I.; Negrebetsky, V.V. Reaction of Picolinamides with Ketones Producing a New Type of Heterocyclic Salts with an Imidazolidin-4-One Ring. Molecules 2024, 29, 206.

Abstract

Reactions of picolinamides with 1,3-propanesultone in methanol followed by the treatment with ketones led to a series of previously unknown chemical transformations, yielding first pyridinium salts (2a-f) with a protonated endocyclic nitrogen atom and then heterocyclic salts (3a-j) containing a 4-imidazoline ring. The structures of intermediate and final products were determined by IR and 1H, 13C NMR spectroscopy and X-ray study. The effects of the ketone and alcohol structures on the product yield were studied by quantum-chemical calculations. The stability of salts 3a-j towards hydrolysis and alcoholysis makes them excellent candidates for the search of new types of biologically active compounds.

Keywords

Subject

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Reaction of Picolinamides with Ketones Producing a New Type of Heterocyclic Salts With a 4-Imidazoline Ring

Abstract

Keywords

Subject

Comments (0)