Work

Assembly of CF 3 -Pyrazole–Triazole Hybrids through (3 + 3)-Cycloaddition/Ring Contraction and Click Chemistry

Year: 2026

Type: article

Abstract: A concise three-step approach for the construction of trifluoromethylated pyrazole–1,2,3-triazole hybrids, considered a promising platform for the discovery of new pharmaceuticals and agrochemicals, is described. The sequence involves ( i ) (3 + 3)-cycloaddition of in situ -generated nitrile imines with mercaptoacetaldehyde followed by spontaneous ring contraction, ( ii ) a C(5)-selective azide transfer, and ( iii ) a copper-catalyzed Huisgen–Meldal–Sharpless click cycloaddition. The devised protocol enables the preparation of a broad array of target structures, including drug-inspired analogues and chiral representatives, obtained in moderate to high overall yields. Subsequent functional group interconversions on the hybrids provide access to synthetically valuable motifs such as aldehydes, amines, carboxylic acids, esters, and amide. The structure of a representative product was confirmed by X-ray analysis.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.5c03120

Authors: Kamil Świątek, Greta Utecht-Jarzyńska, Barbara Olszewska, Katarzyna Gach-Janczak, Marcin Jasiński

Institutions: University of Łódź, Medical University of Lodz

Language: English

Topic: Click Chemistry and Applications

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: Uniwersytet Łódzki