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-(50-hydroxymethyl-20-furyl)-indazole (YC-1), an important pharmaceutical target.
Efficient Two-Step Sequence for the Synthesis of 2,5-Disubstituted Furan Derivatives from Functionalized Nitroalkanes: Successive Amberlyst A21- and Amberlyst 15-Catalyzed Processes
PALMIERI, Alessandro;GABRIELLI, Serena;BALLINI, Roberto
2010-01-01
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-(50-hydroxymethyl-20-furyl)-indazole (YC-1), an important pharmaceutical target.File in questo prodotto:
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