Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

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

Version 1 : Received: 6 November 2023 / Approved: 7 November 2023 / Online: 7 November 2023 (12:31:16 CET)

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

4-imidazolidinones; sulfobetaines; NMR and FT-IR spectroscopy; X-ray study; quantum-chemical calculations

Subject

Chemistry and Materials Science, Organic Chemistry

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