Chemo- and regioselective defluorinative annulation of (trifluoromethyl)alkenes with pyrazolones: synthesis and insecticidal activity of 6-fluoro-1,4-dihydropyrano[2,3-c]pyrazoles†
Abstract
The chemo- and regioselective defluorinative [3 + 3] annulation of (trifluoromethyl)alkenes and pyrazolones is reported that gives rise to various useful 6-fluoro-1,4-dihydropyrano[2,3-c]pyrazoles in high yields. This reaction distinguishes the different nucleophilic sites of pyrazolones and features mild conditions, a broad substrate scope, and gram-scalability. A simple derivation of the obtained 6-fluoro-1,4-dihydropyrano[2,3-c]pyrazoles efficiently afforded diverse useful compounds. Significantly, compound 3w exhibits up to 100% insecticidal activity against Plutella xylostella, which is a destructive pest worldwide. Mechanism studies indicate that this reaction proceeds via a chemo- and regioselective SN2′/SNV pathway and that the double defluorinative alkylation of pyrazolones with (trifluoromethyl)alkenes is completely inhibited.
![Graphical abstract: Chemo- and regioselective defluorinative annulation of (trifluoromethyl)alkenes with pyrazolones: synthesis and insecticidal activity of 6-fluoro-1,4-dihydropyrano[2,3-c]pyrazoles](/en/Image/Get?imageInfo.ImageType=GA&imageInfo.ImageIdentifier.ManuscriptID=D2QO00786J&imageInfo.ImageIdentifier.Year=2022)
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