Literature DB >> 20657907

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

Alessandro Palmieri1, Serena Gabrielli, Roberto 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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Year:  2010        PMID: 20657907     DOI: 10.1039/c0cc01097a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  2 in total

1.  Comparison of Substituting Ability of Nitronate versus Enolate for Direct Substitution of a Nitro Group.

Authors:  Yusuke Mukaijo; Soichi Yokoyama; Nagatoshi Nishiwaki
Journal:  Molecules       Date:  2020-04-28       Impact factor: 4.411

2.  A New Valuable Synthesis of Polyfunctionalized Furans Starting from β-Nitroenones and Active Methylene Compounds.

Authors:  Elena Chiurchiù; Serena Gabrielli; Roberto Ballini; Alessandro Palmieri
Journal:  Molecules       Date:  2019-12-13       Impact factor: 4.411

  2 in total

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