The study of the reaction paths of 4-aryl-4-oxobutanoic acids with terminal aliphatic N,N-diamines
Bicyclic pyrroloimidazolones and pyrrolopyrimidinones were synthesized by reacting aryl-substituted 4-oxobutanoic acids with aliphatic binucleophiles with different alkyl chain lengths using a sealed vessels reactor (SVR). By varying the synthesis conditions, the reaction path was studied and formed...
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| Format: | Article |
| Language: | English |
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Elsevier
2021-10-01
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| Series: | Arabian Journal of Chemistry |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535221003658 |
| _version_ | 1818902954732683264 |
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| author | Elena I. Linkova Vyacheslav S. Grinev Oksana A. Mayorova Alevtina Yu. Yegorova |
| author_facet | Elena I. Linkova Vyacheslav S. Grinev Oksana A. Mayorova Alevtina Yu. Yegorova |
| author_sort | Elena I. Linkova |
| collection | DOAJ |
| description | Bicyclic pyrroloimidazolones and pyrrolopyrimidinones were synthesized by reacting aryl-substituted 4-oxobutanoic acids with aliphatic binucleophiles with different alkyl chain lengths using a sealed vessels reactor (SVR). By varying the synthesis conditions, the reaction path was studied and formed intermediates were isolated. The structures of the obtained compounds were proved using a set of FTIR, 1H, 13C NMR spectroscopy methods and X-ray diffraction data. Temperature and pressure changes data collected during the syntheses were analyzed and assigned to the processes which occurred inside the vials. It was shown that the reaction of 4-aryl-4-oxobutanoic acids with terminal aliphatic N,N-diamines starts from the formation of corresponded (AlkN2)2+An2- salts followed by two subsequent dehydration processes giving rise to the corresponding amides and, finally, heterocycles of pyrroloimidazolone and pyrrolopyrimidinone series. |
| first_indexed | 2024-12-19T20:43:51Z |
| format | Article |
| id | doaj.art-00d618479a744ce5ae664ba44fda88b8 |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-12-19T20:43:51Z |
| publishDate | 2021-10-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-00d618479a744ce5ae664ba44fda88b82022-12-21T20:06:19ZengElsevierArabian Journal of Chemistry1878-53522021-10-011410103350The study of the reaction paths of 4-aryl-4-oxobutanoic acids with terminal aliphatic N,N-diaminesElena I. Linkova0Vyacheslav S. Grinev1Oksana A. Mayorova2Alevtina Yu. Yegorova3Institute of Chemistry, Chernyshevsky Saratov State University, Ulitsa Astrakhanskaya, 83, 410012, RussiaInstitute of Chemistry, Chernyshevsky Saratov State University, Ulitsa Astrakhanskaya, 83, 410012, Russia; Institute of Biochemistry and Physiology of Plants and Microorganisms RAS, Prospekt Entuziastov, 13, 410049, Russia; Corresponding author at: Institute of Chemistry, Chernyshevsky Saratov State University, Ulitsa Astrakhanskaya, 83, 410012, Russia.Institute of Biochemistry and Physiology of Plants and Microorganisms RAS, Prospekt Entuziastov, 13, 410049, RussiaInstitute of Chemistry, Chernyshevsky Saratov State University, Ulitsa Astrakhanskaya, 83, 410012, RussiaBicyclic pyrroloimidazolones and pyrrolopyrimidinones were synthesized by reacting aryl-substituted 4-oxobutanoic acids with aliphatic binucleophiles with different alkyl chain lengths using a sealed vessels reactor (SVR). By varying the synthesis conditions, the reaction path was studied and formed intermediates were isolated. The structures of the obtained compounds were proved using a set of FTIR, 1H, 13C NMR spectroscopy methods and X-ray diffraction data. Temperature and pressure changes data collected during the syntheses were analyzed and assigned to the processes which occurred inside the vials. It was shown that the reaction of 4-aryl-4-oxobutanoic acids with terminal aliphatic N,N-diamines starts from the formation of corresponded (AlkN2)2+An2- salts followed by two subsequent dehydration processes giving rise to the corresponding amides and, finally, heterocycles of pyrroloimidazolone and pyrrolopyrimidinone series.http://www.sciencedirect.com/science/article/pii/S1878535221003658SynthesisPyrroloimidazolonesPyrrolopyrimidinonesIntermediatesProcess schemeReaction path |
| spellingShingle | Elena I. Linkova Vyacheslav S. Grinev Oksana A. Mayorova Alevtina Yu. Yegorova The study of the reaction paths of 4-aryl-4-oxobutanoic acids with terminal aliphatic N,N-diamines Arabian Journal of Chemistry Synthesis Pyrroloimidazolones Pyrrolopyrimidinones Intermediates Process scheme Reaction path |
| title | The study of the reaction paths of 4-aryl-4-oxobutanoic acids with terminal aliphatic N,N-diamines |
| title_full | The study of the reaction paths of 4-aryl-4-oxobutanoic acids with terminal aliphatic N,N-diamines |
| title_fullStr | The study of the reaction paths of 4-aryl-4-oxobutanoic acids with terminal aliphatic N,N-diamines |
| title_full_unstemmed | The study of the reaction paths of 4-aryl-4-oxobutanoic acids with terminal aliphatic N,N-diamines |
| title_short | The study of the reaction paths of 4-aryl-4-oxobutanoic acids with terminal aliphatic N,N-diamines |
| title_sort | study of the reaction paths of 4 aryl 4 oxobutanoic acids with terminal aliphatic n n diamines |
| topic | Synthesis Pyrroloimidazolones Pyrrolopyrimidinones Intermediates Process scheme Reaction path |
| url | http://www.sciencedirect.com/science/article/pii/S1878535221003658 |
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