Preparation of 5-substituted 3-aminofuran-2-carboxylate esters

Org Lett. 2000 Jul 13;2(14):2061-3. doi: 10.1021/ol0059652.

Abstract

[reaction: see text] An efficient method for the preparation of 3-aminofuran-2-carboxylate esters has been developed. This method is based on the reaction of an alpha-cyanoketone with ethyl glyoxylate under Mitsunobu conditions to produce a vinyl ether in good yield. Subsequent treatment of the vinyl ether with sodium hydride afforded the 3-aminofuran. It was also found that a one-pot procedure using the Mitsunobu reaction followed by cyclization afforded the 3-aminofuran in comparable yield. Currently, this method is limited to the synthesis of 5-alkyl-, 5-aryl-, and 4,5-fused bicyclic furans.

MeSH terms

  • Alkylation
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
  • Esters / chemical synthesis*
  • Furans / chemical synthesis*

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Esters
  • Furans