Acid Catalyzed <i>N</i>-Alkylation of Pyrazoles with Trichloroacetimidates
<i>N</i>-Alkyl pyrazoles are important heterocycles in organic and medicinal chemistry, demonstrating a wide range of biological activity. A new method for the <i>N</i>-alkylation of pyrazoles has been developed using trichloroacetimidate electrophiles and a Brønsted acid cat...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-05-01
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| Series: | Organics |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2673-401X/3/2/9 |
| Summary: | <i>N</i>-Alkyl pyrazoles are important heterocycles in organic and medicinal chemistry, demonstrating a wide range of biological activity. A new method for the <i>N</i>-alkylation of pyrazoles has been developed using trichloroacetimidate electrophiles and a Brønsted acid catalyst. These reactions provide ready access to <i>N</i>-alkyl pyrazoles which are present in a variety of medicinally relevant lead structures. Benzylic, phenethyl and benzhydryl trichloroacetimidates provide good yields of the <i>N</i>-alkyl pyrazole products. Unsymmetrical pyrazoles provide a mixture of the two possible regioisomers, with the major product being controlled by sterics. This methodology provides an alternative to other alkylation methods that require strong base or high temperature. |
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| ISSN: | 2673-401X |