Efficient two-step sequence for the synthesis of 2,5-disubstituted furan derivatives from functionalized nitroalkanes: successive Amberlyst A21- and Amberlyst 15-catalyzed processes

Chemical Communications : Chem Comm
Alessandro PalmieriRoberto Ballini

Abstract

The nitroaldol reaction of ketal-functionalized nitroalkanes with alpha-oxoaldehydes, promoted by Amberlyst A21, followed by acidic treatment (Amberlyst 15) of the obtained nitroalkanol, leads to the formation of 2,5-disubstituted furans in good yields. The procedure was successfully applied to the total synthesis of 1-benzyl-3-(5'-hydroxymethyl-2'-furyl)-indazole (YC-1), an important pharmaceutical target.

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Citations

Dec 19, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Elena ChiurchiùAlessandro Palmieri
May 2, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yusuke MukaijoNagatoshi Nishiwaki
Nov 26, 2014·Chemical Reviews·Bagher Eftekhari-Sis, Maryam Zirak
May 21, 2015·The Journal of Organic Chemistry·Wei ZhangYunkui Liu

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