Reaction of Picolinamides with Ketones Producing a New Type of Heterocyclic Salts with an Imidazolidin-4-One Ring | Sciact - CRIS-system of Boreskov Institute of Catalysis

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

Journal

Molecules
ISSN: 1420-3049

Output data

Year: 2024, Volume: 29, Number: 1, Article number : 206, Pages count : 18 DOI: 10.3390/molecules29010206

Tags

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

Authors

Kramarova Eugenia P. ¹ , Lyakhmun Dmitry N. ¹ , Tarasenko Dmitry V. ¹ , Borisevich Sophia S. ² , Khamitov Edward M. ² , Yusupova Alfia R. ² , Korlyukov Alexander A. ^3,1 , Romanenko Alexander R. ^3,4 , Shmigol Tatiana A. ¹ , Bylikin Sergey Yu. ⁵ , Baukov Yuri I. ¹ , Negrebetsky Vadim V. ¹

Affiliations

1	Institute of Pharmacy and Medical Chemistry, Pirogov Russian National Research Medical University, Ostrovityanov St., Bl. 1, 117997 Moscow, Russia
2	Ufa Institute of Chemistry, Oktyabrya Aven., 71, 450054 Ufa, Russia
3	A.N.Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilova St. 28, Bl. 1, 119334 Moscow, Russia
4	D.I. Mendeleev Russian University of Chemical Technology, Miusskaya Sq., 9, 125047 Moscow, Russia
5	The Open University, Walton Hall, Milton Keynes MK7 6BJ, UK

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.

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. V.29. N1. 206 :1-18. DOI: 10.3390/molecules29010206 WOS Scopus ANCAN PMID OpenAlex

Submitted:	Nov 2, 2023
Accepted:	Dec 22, 2023
Published online:	Dec 29, 2023
Published print:	Jan 1, 2024

Web of science:	WOS:001140618200001
Scopus:	2-s2.0-85181928741
Chemical Abstracts:	2024:138166
Chemical Abstracts (print):	186:99891
PMID:	38202789
OpenAlex:	W4390412533

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