期刊
CCS CHEMISTRY
卷 4, 期 12, 页码 3693-3704出版社
CHINESE CHEMICAL SOC
DOI: 10.31635/ccschem.022.202201923
关键词
pyrazoles; trifluoromethyl group; cyano group; silver catalysis; diazo reagents
资金
- National Natural Science Foundation of China [92156025, 21901181, 21961142015]
- National Key Research and Development Program of China [2019YFA0905100, 2021YFF0701700]
- Tianjin Municipal Science and Technology Commission [19JCQNJC04700]
The article presents a silver-catalyzed [3 + 2] cycloaddition reaction that enables the incorporation of trifluoromethyl and cyano moieties into a heterocyclic core in a single-step reaction. This method allows for the synthesis of pyrazoles decorated with both trifluoromethyl and cyano groups, which can be used as cyano-analogues of CF3-containing drugs and agrochemicals. Some of these compounds show enhanced inhibitory activity towards cyclooxygenase-2, suggesting their potential as lead-based anti-inflammatory agents.
The dual incorporation of two important functional groups-trifluoromethyl and cyano moieties into one heterocyclic core in a single-step reaction represents an appealing but largely unaddressed synthetic challenge. Here we demonstrate that a silver-catalyzed [3 + 2] cycloaddition reaction of dicyanoalkenes with trifluorodiazoethane (CF3CHN2) could render a facile construction of a unique category of pyrazoles that are simultaneously adorned by trifluoromethyl and cyano groups. Changing the location pattern of the cyano group in starting dicyanoalkene material allows regiodivergent access to two series of previously elusive trifluoromethyl cyanopyrazoles with an exquisite level of regiocontrol. Thus, this method could be applied in the preparation of cyano-analogues of CF3-containing drugs (Celecoxib) and agrochemicals (Penthiopyrad and Fluazolate). Notably, several cyano-analogues of Celecoxib demonstrate enhanced inhibitory activity towards cyclooxygenase-2 (COX-2), thereby laying a good foundation for developing new lead-based anti-inflammatory agents. [GRAPHICS] .
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