Preparation of 5-substituted 3-aminofuran-2-carboxylate esters.
[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.
Redman
A M
AM
Department of Chemistry Research, Bayer Research Center, West Haven, Connecticut 06516, USA. aniko.redman.b@bayer.com
Dumas
J
J
Scott
W J
WJ
D000478:Alkylation; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis*; D004952:Esters / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis*
D000894:Anti-Inflammatory Agents, Non-Steroidal; D004952:Esters; D005663:Furans