Switching N-Alkylation Regioselectivity of Trifluoromethylated Pyrazoles Guided by Functional Group Tuning
The similar properties of the nitrogen atoms in azole ring complicate the regioselective <i>N</i>-functionalization of pyrazoles. This work demonstrates the role of the hydrazone substituent in the control of the alkylation selectivity of (trifluoromethyl)pyrazoles. Reaction conditions for the synthesis of 3- and 5-(trifluoromethyl)pyrazoles were developed, and all types of regioisomers formed under the alkylation of bis-pyrazolyl <i>NH</i>-ketazine were isolated. The structures of the synthesized compounds were confirmed by NMR spectroscopy and XRD data.
Authors
- Yulia S. Kudyakova (ORCID: https://orcid.org/0000-0003-0637-1606)
- Ekaterina A. Osipova
- Павел А. Слепухин (ORCID: https://orcid.org/0000-0001-8132-9905)
- Денис Н. Бажин (ORCID: https://orcid.org/0000-0003-3972-6995)
- Yulia O. Edilova (ORCID: https://orcid.org/0000-0001-8955-6272)
- Yanina V. Burgart (ORCID: https://orcid.org/0000-0001-6061-2410)
- В. И. Салоутин (ORCID: https://orcid.org/0000-0003-1976-7861)
Institutions
- Ural Federal University (RU)
- Institute of Organic Synthesis (RU)
- Ural Branch of the Russian Academy of Sciences (RU)
Publication Details
- Journal
- International Journal of Molecular Sciences
- Published
- 2025-10-23
- DOI
- https://doi.org/10.3390/ijms262110335
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00