Unexpected Tellurohalogenation of Terminal N‐Alkynyl (Alkenyl) Derivatives of 4‐Functionalized Pyrazoles
Abstract The efficient synthesis of terminal N‐alkenyl and N‐alkynyl derivatives of pyrazole‐4‐carboxylic acids and their methyl esters as substrates for studying electrophilic heterocyclization has been reported. The regiochemistry and stereoselectivity of the tellurium‐induced heterocyclization of...
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| Format: | Article |
| Language: | English |
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Wiley-VCH
2025-08-01
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| Series: | ChemistryOpen |
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| Online Access: | https://doi.org/10.1002/open.202400486 |
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| author | Marianna V. Povidaichyk Svitlana V. Shishkina Eugeniy M. Ostapchuk Prof. Mykhaylo Yu. Onysko |
| author_facet | Marianna V. Povidaichyk Svitlana V. Shishkina Eugeniy M. Ostapchuk Prof. Mykhaylo Yu. Onysko |
| author_sort | Marianna V. Povidaichyk |
| collection | DOAJ |
| description | Abstract The efficient synthesis of terminal N‐alkenyl and N‐alkynyl derivatives of pyrazole‐4‐carboxylic acids and their methyl esters as substrates for studying electrophilic heterocyclization has been reported. The regiochemistry and stereoselectivity of the tellurium‐induced heterocyclization of 1‐pentynyl (butynyl, butenyl) substituted pyrazole‐4‐carboxylic acids and their methyl esters under the action of tellurium (IV) oxide in hydrohalic acid were determined. This electrophilic heterocyclization leads to the formation of tetrahydropyrazolo[1,2‐a]pyridazinium and dihydropyrazolo[1,2‐a]pyrazolium intramolecular salts, as confirmed by X‐ray diffraction (XRD) and comprehensive spectral analysis. |
| format | Article |
| id | doaj-art-9103512a8a024de69248ee907dc7d89e |
| institution | Kabale University |
| issn | 2191-1363 |
| language | English |
| publishDate | 2025-08-01 |
| publisher | Wiley-VCH |
| record_format | Article |
| series | ChemistryOpen |
| spelling | doaj-art-9103512a8a024de69248ee907dc7d89e2025-08-21T12:05:32ZengWiley-VCHChemistryOpen2191-13632025-08-01148n/an/a10.1002/open.202400486Unexpected Tellurohalogenation of Terminal N‐Alkynyl (Alkenyl) Derivatives of 4‐Functionalized PyrazolesMarianna V. Povidaichyk0Svitlana V. Shishkina1Eugeniy M. Ostapchuk2Prof. Mykhaylo Yu. Onysko3Department of Uzhhorod national university 3 Narodna Sq Uzhhorod UkraineDepartment of X-ray Diffraction Studies and Quantum Chemistry SSI “Institute for Single Crystals” NAS of Ukraine 60 Nauky ave. Kharkiv UkraineEnamine Ltd 78 Winston Churchill St Kyiv UkraineDepartment of Uzhhorod national university 3 Narodna Sq Uzhhorod UkraineAbstract The efficient synthesis of terminal N‐alkenyl and N‐alkynyl derivatives of pyrazole‐4‐carboxylic acids and their methyl esters as substrates for studying electrophilic heterocyclization has been reported. The regiochemistry and stereoselectivity of the tellurium‐induced heterocyclization of 1‐pentynyl (butynyl, butenyl) substituted pyrazole‐4‐carboxylic acids and their methyl esters under the action of tellurium (IV) oxide in hydrohalic acid were determined. This electrophilic heterocyclization leads to the formation of tetrahydropyrazolo[1,2‐a]pyridazinium and dihydropyrazolo[1,2‐a]pyrazolium intramolecular salts, as confirmed by X‐ray diffraction (XRD) and comprehensive spectral analysis.https://doi.org/10.1002/open.202400486Alkynyl(alkenyl)pyrazoleDihydropyrazolo[1.2-a]pyrazolium saltsElectrophilic heterocyclizationTetrahydropyrazolo[1,2-a]pyridazinium saltsZwitterion |
| spellingShingle | Marianna V. Povidaichyk Svitlana V. Shishkina Eugeniy M. Ostapchuk Prof. Mykhaylo Yu. Onysko Unexpected Tellurohalogenation of Terminal N‐Alkynyl (Alkenyl) Derivatives of 4‐Functionalized Pyrazoles ChemistryOpen Alkynyl(alkenyl)pyrazole Dihydropyrazolo[1.2-a]pyrazolium salts Electrophilic heterocyclization Tetrahydropyrazolo[1,2-a]pyridazinium salts Zwitterion |
| title | Unexpected Tellurohalogenation of Terminal N‐Alkynyl (Alkenyl) Derivatives of 4‐Functionalized Pyrazoles |
| title_full | Unexpected Tellurohalogenation of Terminal N‐Alkynyl (Alkenyl) Derivatives of 4‐Functionalized Pyrazoles |
| title_fullStr | Unexpected Tellurohalogenation of Terminal N‐Alkynyl (Alkenyl) Derivatives of 4‐Functionalized Pyrazoles |
| title_full_unstemmed | Unexpected Tellurohalogenation of Terminal N‐Alkynyl (Alkenyl) Derivatives of 4‐Functionalized Pyrazoles |
| title_short | Unexpected Tellurohalogenation of Terminal N‐Alkynyl (Alkenyl) Derivatives of 4‐Functionalized Pyrazoles |
| title_sort | unexpected tellurohalogenation of terminal n alkynyl alkenyl derivatives of 4 functionalized pyrazoles |
| topic | Alkynyl(alkenyl)pyrazole Dihydropyrazolo[1.2-a]pyrazolium salts Electrophilic heterocyclization Tetrahydropyrazolo[1,2-a]pyridazinium salts Zwitterion |
| url | https://doi.org/10.1002/open.202400486 |
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