Pyrrole–Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles
An efficient method for the synthesis of pharmaceutically prospective pyrrole–aminopyrimidine ensembles (in up to 91% yield) by the cyclocondensation of easily available acylethynylpyrroles with guanidine nitrate has been developed. The reaction proceeds under heating (110–115 °C, 4 h) in the KOH/DM...
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MDPI AG
2021-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/6/1692 |
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| author | Olga V. Petrova Arsalan B. Budaev Elena F. Sagitova Igor A. Ushakov Lyubov N. Sobenina Andrey V. Ivanov Boris A. Trofimov |
| author_facet | Olga V. Petrova Arsalan B. Budaev Elena F. Sagitova Igor A. Ushakov Lyubov N. Sobenina Andrey V. Ivanov Boris A. Trofimov |
| author_sort | Olga V. Petrova |
| collection | DOAJ |
| description | An efficient method for the synthesis of pharmaceutically prospective pyrrole–aminopyrimidine ensembles (in up to 91% yield) by the cyclocondensation of easily available acylethynylpyrroles with guanidine nitrate has been developed. The reaction proceeds under heating (110–115 °C, 4 h) in the KOH/DMSO system. In the case of 2-benzoylethynylpyrrole, the unexpected addition of the formed pyrrole–aminopyrimidine as N- (NH moiety of the pyrrole ring) and C- (CH of aminopyrimidine) nucleophiles to the triple bond is observed. |
| first_indexed | 2024-03-10T13:08:29Z |
| format | Article |
| id | doaj.art-2987eee0312940a49f472ed2f63d00bc |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T13:08:29Z |
| publishDate | 2021-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-2987eee0312940a49f472ed2f63d00bc2023-11-21T10:55:50ZengMDPI AGMolecules1420-30492021-03-01266169210.3390/molecules26061692Pyrrole–Aminopyrimidine Ensembles: Cycloaddition of Guanidine to AcylethynylpyrrolesOlga V. Petrova0Arsalan B. Budaev1Elena F. Sagitova2Igor A. Ushakov3Lyubov N. Sobenina4Andrey V. Ivanov5Boris A. Trofimov6A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, RussiaA.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, RussiaA.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, RussiaA.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, RussiaA.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, RussiaA.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, RussiaA.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, RussiaAn efficient method for the synthesis of pharmaceutically prospective pyrrole–aminopyrimidine ensembles (in up to 91% yield) by the cyclocondensation of easily available acylethynylpyrroles with guanidine nitrate has been developed. The reaction proceeds under heating (110–115 °C, 4 h) in the KOH/DMSO system. In the case of 2-benzoylethynylpyrrole, the unexpected addition of the formed pyrrole–aminopyrimidine as N- (NH moiety of the pyrrole ring) and C- (CH of aminopyrimidine) nucleophiles to the triple bond is observed.https://www.mdpi.com/1420-3049/26/6/1692acylethynylpyrrolesguanidinecyclocondensationaminopyrimidine |
| spellingShingle | Olga V. Petrova Arsalan B. Budaev Elena F. Sagitova Igor A. Ushakov Lyubov N. Sobenina Andrey V. Ivanov Boris A. Trofimov Pyrrole–Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles Molecules acylethynylpyrroles guanidine cyclocondensation aminopyrimidine |
| title | Pyrrole–Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles |
| title_full | Pyrrole–Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles |
| title_fullStr | Pyrrole–Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles |
| title_full_unstemmed | Pyrrole–Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles |
| title_short | Pyrrole–Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles |
| title_sort | pyrrole aminopyrimidine ensembles cycloaddition of guanidine to acylethynylpyrroles |
| topic | acylethynylpyrroles guanidine cyclocondensation aminopyrimidine |
| url | https://www.mdpi.com/1420-3049/26/6/1692 |
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