Reaction of Picolinamides with Ketones Producing a New Type of Heterocyclic Salts with an Imidazolidin-4-One Ring
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 (<b>2a</b>–<b>f</b>), with a protonated endocyclic nitrogen atom, and then het...
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| Format: | Article |
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MDPI AG
2023-12-01
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| Online Access: | https://www.mdpi.com/1420-3049/29/1/206 |
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| author | Eugenia P. Kramarova Dmitry N. Lyakhmun Dmitry V. Tarasenko Sophia S. Borisevich Edward M. Khamitov Alfia R. Yusupova Alexander A. Korlyukov Alexander R. Romanenko Tatiana A. Shmigol Sergey Yu. Bylikin Yuri I. Baukov Vadim V. Negrebetsky |
| author_facet | Eugenia P. Kramarova Dmitry N. Lyakhmun Dmitry V. Tarasenko Sophia S. Borisevich Edward M. Khamitov Alfia R. Yusupova Alexander A. Korlyukov Alexander R. Romanenko Tatiana A. Shmigol Sergey Yu. Bylikin Yuri I. Baukov Vadim V. Negrebetsky |
| author_sort | Eugenia P. Kramarova |
| collection | DOAJ |
| description | 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 (<b>2a</b>–<b>f</b>), with a protonated endocyclic nitrogen atom, and then heterocyclic salts (<b>3a</b>–<b>j</b>) containing an imidazolidin-4-one ring. The structures of intermediate and final products were determined by IR and <sup>1</sup>H, <sup>13</sup>C 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 <b>3a</b>–<b>j</b> towards hydrolysis and alcoholysis makes them excellent candidates for the search for new types of biologically active compounds. |
| first_indexed | 2024-03-08T15:01:00Z |
| format | Article |
| id | doaj.art-05cadb494caf4f7d937001910e5fd9c4 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-08T15:01:00Z |
| publishDate | 2023-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-05cadb494caf4f7d937001910e5fd9c42024-01-10T15:04:29ZengMDPI AGMolecules1420-30492023-12-0129120610.3390/molecules29010206Reaction of Picolinamides with Ketones Producing a New Type of Heterocyclic Salts with an Imidazolidin-4-One RingEugenia P. Kramarova0Dmitry N. Lyakhmun1Dmitry V. Tarasenko2Sophia S. Borisevich3Edward M. Khamitov4Alfia R. Yusupova5Alexander A. Korlyukov6Alexander R. Romanenko7Tatiana A. Shmigol8Sergey Yu. Bylikin9Yuri I. Baukov10Vadim V. Negrebetsky11Institute of Pharmacy and Medical Chemistry, Pirogov Russian National Research Medical University, Ostrovityanov St., Bl. 1, 117997 Moscow, RussiaInstitute of Pharmacy and Medical Chemistry, Pirogov Russian National Research Medical University, Ostrovityanov St., Bl. 1, 117997 Moscow, RussiaInstitute of Pharmacy and Medical Chemistry, Pirogov Russian National Research Medical University, Ostrovityanov St., Bl. 1, 117997 Moscow, RussiaUfa Institute of Chemistry, Oktyabrya Aven., 71, 450054 Ufa, RussiaUfa Institute of Chemistry, Oktyabrya Aven., 71, 450054 Ufa, RussiaUfa Institute of Chemistry, Oktyabrya Aven., 71, 450054 Ufa, RussiaInstitute of Pharmacy and Medical Chemistry, Pirogov Russian National Research Medical University, Ostrovityanov St., Bl. 1, 117997 Moscow, RussiaA.N.Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilova St. 28, Bl. 1, 119334 Moscow, RussiaInstitute of Pharmacy and Medical Chemistry, Pirogov Russian National Research Medical University, Ostrovityanov St., Bl. 1, 117997 Moscow, RussiaThe Open University, Walton Hall, Milton Keynes MK7 6BJ, UKInstitute of Pharmacy and Medical Chemistry, Pirogov Russian National Research Medical University, Ostrovityanov St., Bl. 1, 117997 Moscow, RussiaInstitute of Pharmacy and Medical Chemistry, Pirogov Russian National Research Medical University, Ostrovityanov St., Bl. 1, 117997 Moscow, RussiaReactions 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 (<b>2a</b>–<b>f</b>), with a protonated endocyclic nitrogen atom, and then heterocyclic salts (<b>3a</b>–<b>j</b>) containing an imidazolidin-4-one ring. The structures of intermediate and final products were determined by IR and <sup>1</sup>H, <sup>13</sup>C 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 <b>3a</b>–<b>j</b> towards hydrolysis and alcoholysis makes them excellent candidates for the search for new types of biologically active compounds.https://www.mdpi.com/1420-3049/29/1/206imidazolidin-4-onessulfobetainesNMR and FT-IR spectroscopyX-ray studyquantum-chemical calculations |
| spellingShingle | Eugenia P. Kramarova Dmitry N. Lyakhmun Dmitry V. Tarasenko Sophia S. Borisevich Edward M. Khamitov Alfia R. Yusupova Alexander A. Korlyukov Alexander R. Romanenko Tatiana A. Shmigol Sergey Yu. Bylikin Yuri I. Baukov Vadim V. Negrebetsky Reaction of Picolinamides with Ketones Producing a New Type of Heterocyclic Salts with an Imidazolidin-4-One Ring Molecules imidazolidin-4-ones sulfobetaines NMR and FT-IR spectroscopy X-ray study quantum-chemical calculations |
| title | Reaction of Picolinamides with Ketones Producing a New Type of Heterocyclic Salts with an Imidazolidin-4-One Ring |
| title_full | Reaction of Picolinamides with Ketones Producing a New Type of Heterocyclic Salts with an Imidazolidin-4-One Ring |
| title_fullStr | Reaction of Picolinamides with Ketones Producing a New Type of Heterocyclic Salts with an Imidazolidin-4-One Ring |
| title_full_unstemmed | Reaction of Picolinamides with Ketones Producing a New Type of Heterocyclic Salts with an Imidazolidin-4-One Ring |
| title_short | Reaction of Picolinamides with Ketones Producing a New Type of Heterocyclic Salts with an Imidazolidin-4-One Ring |
| title_sort | reaction of picolinamides with ketones producing a new type of heterocyclic salts with an imidazolidin 4 one ring |
| topic | imidazolidin-4-ones sulfobetaines NMR and FT-IR spectroscopy X-ray study quantum-chemical calculations |
| url | https://www.mdpi.com/1420-3049/29/1/206 |
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