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Synthesis of new aryl substituted furan-2(5H)-ones using the Suzuki-Miyaura reaction |
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| Authors: | Ruonan ZhangGeorge Iskander Paulo da SilvaDaniel Chan Valentina VignevichVi Nguyen Mohan M. BhadbhadeDavid StC Black Naresh Kumar |
| Affiliation: | a School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia b Analytical Centre, The University of New South Wales, Sydney, NSW 2052, Australia |
| Abstract: | A series of novel 5-arylidenefuran-2(5H)-ones and 5-arylidene-4-arylfuran-2(5H)-ones were synthesized via the Suzuki-Miyaura reactions of fimbrolide derivatives 5-(bromomethylene)furan-2(5H)-one and 4-bromo-5-(bromomethylene)furan-2(5H)-one, respectively. A regioselective Suzuki-Miyaura reaction on 4-bromo-5-(bromomethylene)furan-2(5H)-one allowed the synthesis of unsymmetrically substituted 5-arylidene-4-arylfuran-2(5H)-ones. The crystal structure of the intermediate 5-arylidene-4-bromofuran-2(5H)-one revealed interesting Br?O halogen bonding. |
| Keywords: | Furanone Suzuki-Miyaura Fimbrolide Antibacterial |
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