One-pot synthesis of 3-aminofurans using a simple and efficient recyclable CuI/[bmim]PF₆ system

Abstract

The one-pot three-component reaction of several 2-ketoaldehdyes, secondary amines and terminal alkynes to access 3-aminofurans was proceeded well in [bmim][PF6] using a simple and cheap CuI catalyst. The resulted 3-aminofuran...

Biomass to Aromatic Amine Module: Alkali Catalytic Conversion of N‐Acetylglucosamine into Unsubstituted 3‐Acetamidofuran by Retro‐Aldol Condensation

“…The groups of Li [18] and Leroux [19] both developed this method to prepare polysubstituted 3‐amino furans and 3‐amino‐5‐fluoroalkylfurans in quantitative or nearly quantitative yields (Scheme 1a). Guguloth and co‐workers [20] obtained 3‐aminofuran derivatives with substituent groups at the 2, 3 and 5 positions in yields greater than 80 % through the tandem Mannich‐Grignard addition and intramolecular cyclization of ketoaldehydes, secondary amines and terminal alkyne (Scheme 1b). Based on the reaction of an α‐cyanoketone with ethyl glyoxylate under Mitsunobu conditions, Scott and co‐workers [21] produced 3‐aminofurans with 2‐ and 5‐position substituents via a vinyl ether intermediate (Scheme 1c).…”