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

Chem Commun (Camb). 2010 Sep 7;46(33):6165-7. doi: 10.1039/c0cc01097a. Epub 2010 Jul 23.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkanes / chemistry*
  • Catalysis
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Indazoles / chemical synthesis*
  • Indazoles / chemistry
  • Molecular Structure
  • Nitro Compounds / chemistry*
  • Styrenes / chemistry*

Substances

  • Alkanes
  • Furans
  • Indazoles
  • Nitro Compounds
  • Styrenes
  • amberlyst A21
  • amberlyst-15
  • 3-(5'-hydroxymethyl-2'-furyl)-1-benzylindazole