A new method for the synthesis of α-trifluoromethylated tertiary alcohols bearing coumarins is described. The reaction of 3-(trifluoroacetyl)coumarin and pyrrole provided the target compounds with high yields under catalyst-free, mild conditions. The crystal structure of compound 3fa was investigated by X-ray diffraction analysis. The biological activities, such as in vitro antifungal activity of the α-trifluoromethylated tertiary alcohols against Fusarium graminearum, Fusarium oxysporum, Fusarium moniliforme, Rhizoctonia solani Kuhn, and Phytophthora parasitica var nicotianae, were investigated. The bioassay results indicated that compounds 3ad, 3gd, and 3hd showed broad-spectrum antifungal activity in vitro. Compound 3cd exhibited excellent fungicidal activity against Rhizoctonia solani Kuhn, with an EC50 value of 10.9 ug/mL, which was comparable to that of commercial fungicidal triadimefon (EC50= 6.1 ug/mL). Furthermore, molecular docking study suggested that 3cd had high binding affinities with 1W9U, like argifin.
A highly chemoselective
reaction between α,β-unsaturated
trifluoromethyl ketones with azaarenes under metal-free conditions
was carried out, affording a range of valuable azaarene-equipped CF3-tertiary alcohols in moderate to excellent yields (up to
95% yield) with good tolerance of functional groups, and their structures
were confirmed by NMR, HRMS, and X-ray diffraction for validation.
This method features simple reaction conditions (only solvent), high
atom- and step-economy, and broad substrate scope. Moreover, most
of the target products exhibited promising fungicidal activities,
and compound 3al exhibited 91.65% fungicidal activity
against R. solani, with an EC50 value of 0.18 mg/mL.
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