title: Efficient two-step sequence for the synthesis of 2,5-disubstituted furan derivatives from functionalized nitroalkanes: successive Amberlyst A21- and Amberlyst 15-catalyzed processes.
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.
authors.affiliation: Green Chemistry Group, School of Science and Technology, Chemistry Division, Università di Camerino, Via S. Agostino 1, I-62032, Camerino, Italy.
authors.forename: Alessandro
authors.initials: A
authors.lastname: Palmieri
authors.forename: Serena
authors.initials: S
authors.lastname: Gabrielli
authors.forename: Roberto
authors.initials: R
authors.lastname: Ballini
mesh_terms: 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*
chemical_list: 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