An optimized procedure for the direct and regioselective arylation of 2-acylfurans has been developed. The versatility of this protocol has been evaluated on a series of aryl and heteroaryl halides, thus obtaining a small collection of 2,5-disubstituted furans in moderate to good yields. Finally, the optimized protocol has been successfully applied to the synthesis of the HIV-1 integrase inhibitor 3 and could be further exploited for the generation of novel substituted furans as potential integrase inhibitors.
Franchi, L., Rinaldi, M., Vignaroli, G., Innitzer, A., Radi, M., Botta, M. (2010). Arylation of 2-Furyl 4-Fluorophenyl Ketone: an extension of Heck Chemistry towards Novel Integrase Inhibitors. SYNTHESIS, 22, 3927-3933 [10.1055/s-0030-1258247].
Arylation of 2-Furyl 4-Fluorophenyl Ketone: an extension of Heck Chemistry towards Novel Integrase Inhibitors
FRANCHI, LUIGI;RINALDI, MARTA;VIGNAROLI, GIULIA;INNITZER, ANNA;RADI, MARCO;BOTTA, MAURIZIO
2010-01-01
Abstract
An optimized procedure for the direct and regioselective arylation of 2-acylfurans has been developed. The versatility of this protocol has been evaluated on a series of aryl and heteroaryl halides, thus obtaining a small collection of 2,5-disubstituted furans in moderate to good yields. Finally, the optimized protocol has been successfully applied to the synthesis of the HIV-1 integrase inhibitor 3 and could be further exploited for the generation of novel substituted furans as potential integrase inhibitors.
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https://hdl.handle.net/11365/9469
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