Efficient two-step sequence for the synthesis of 2,5-disubstituted furan derivatives from functionalized nitroalkanes: successive Amberlyst A21- and Amberlyst 15-catalyzed processes.
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.
Palmieri
Alessandro
A
Green Chemistry Group, School of Science and Technology, Chemistry Division, Università di Camerino, Via S. Agostino 1, I-62032, Camerino, Italy.
Gabrielli
Serena
S
Ballini
Roberto
R
D000473:Alkanes / Q000737:chemistry*; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007191:Indazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D013343:Styrenes / Q000737:chemistry*
D000473:Alkanes; D005663:Furans; D007191:Indazoles; D009574:Nitro Compounds; D013343:Styrenes; C554577:amberlyst A21; C528218:amberlyst-15; C090937:3-(5'-hydroxymethyl-2'-furyl)-1-benzylindazole