Reaction of Picolinamides with Ketones Producing a New Type of Heterocyclic Salts with an Imidazolidin-4-One Ring

Kramarova, Eugenia P.; Lyakhmun, Dmitry N.; Tarasenko, Dmitry V.; Borisevich, Sophia S.; Khamitov, Edward M.; Yusupova, Alfia R.; Korlyukov, Alexander A.; Romanenko, Alexander R.; Shmigol, Tatiana A.; Bylikin, Sergey Y.; Baukov, Yuri I. and Negrebetsky, Vadim V. (2023). Reaction of Picolinamides with Ketones Producing a New Type of Heterocyclic Salts with an Imidazolidin-4-One Ring. Molecules, 29(1), article no. 206.

DOI: https://doi.org/10.3390/molecules29010206

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 an imidazolidin-4-one 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 for new types of biologically active compounds.

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