A number of 7-hydroxycoumarins (5), on treatment with one equivalent of (E)-methyl 2-{2-[(chloromethyl)phenyl]}-3-methoxyacrylate (6) at 80°C for 6–8 h, afforded (E)-methyl 2-{2-[(coumarin-7-yloxy)methyl]phenyl}-3-methoxyacrylates (2) in 80–85% yields. The 7-hydroxycoumarins (5) were in turn prepared from resorcinols (3) and substituted ethyl 3-oxopropanoate (4). Subsequently, results of biological activities evaluated in the greenhouse indicated that several of these compounds have good fungicidal activity against cucumber downy mildew (CDM) at 25g ai/ha.
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3, 4, 5a, 5b and 5d are available from chemical reagent company; others were prepared based on the known method: XieL, TakeuchiY, CosentinoM, McPhailAT, LeeK.-H. (2001) Synthesis and anti-HIV activity of disubstituted (3'R, 4'R)-3′,4′-di O-(S)-camphanoyl-(+)-cis-khellactone analogues. Journal of Medicinal Chemistry, 44, 664–671.
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(a) LiuC-L, LiZ-M. (2004) Design, synthesis, and biological activity of a novel lead compound 4-[4-(3,4-dimethoxyphenyl)-2-methylthiazole-5-carbonyl]morpholine. Chinese Journal of Pesticides (Nong Yao), 4, 157–159
