Abstract
2-Methylbenzene-1,4-diol was reacted with ethyl 3-oxobutanoate in concentrated sulfuric acid to generate 6- hydroxycoumarins (2a-b), which were milled with anhydrous K2CO3, aryl chloride under solvent-free conditions, resulting in the formation of C6-esterified coumarins (3a-ss) in good to excellent yields. The structures of all title compounds were confirmed by 1H NMR, MS and elementary analyses. The preliminary bioassay indicated some title compounds, such as 3f, 3h, 3m, 3t, 3u, 3x, 3aa, 3bb, 3ff, 3gg, 3ii, 3ll, and 3nn to have over 90% insecticidal activities against several insects at 100 mg/L.
Keywords: Coumarins, insecticidal activities, solvent-free, synthesis.
Letters in Drug Design & Discovery
Title:Solvent-Free Synthesis and Insecticidal Activities of C6-Esterified Coumarins
Volume: 11 Issue: 9
Author(s): Ying Xie, Zheng-Lin Lei and Yan-Ping Luo
Affiliation:
Keywords: Coumarins, insecticidal activities, solvent-free, synthesis.
Abstract: 2-Methylbenzene-1,4-diol was reacted with ethyl 3-oxobutanoate in concentrated sulfuric acid to generate 6- hydroxycoumarins (2a-b), which were milled with anhydrous K2CO3, aryl chloride under solvent-free conditions, resulting in the formation of C6-esterified coumarins (3a-ss) in good to excellent yields. The structures of all title compounds were confirmed by 1H NMR, MS and elementary analyses. The preliminary bioassay indicated some title compounds, such as 3f, 3h, 3m, 3t, 3u, 3x, 3aa, 3bb, 3ff, 3gg, 3ii, 3ll, and 3nn to have over 90% insecticidal activities against several insects at 100 mg/L.
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Cite this article as:
Xie Ying, Lei Zheng-Lin and Luo Yan-Ping, Solvent-Free Synthesis and Insecticidal Activities of C6-Esterified Coumarins, Letters in Drug Design & Discovery 2014; 11 (9) . https://dx.doi.org/10.2174/1570180811666140603003043
DOI https://dx.doi.org/10.2174/1570180811666140603003043 |
Print ISSN 1570-1808 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-628X |
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