A tandem Mannich addition–palladium catalyzed ring-closing route toward 4-substituted-3(2H)-furanones

Abstract

A facile route towards highly functionalized 3(2H)-furanones via a sequential Mannich addition–palladium catalyzed ring closing has been elaborated. The reaction of 4-chloroacetoacetate esters with imines derived from aliphatic and aromatic aldehydes under palladium catalysis afforded 4-substituted furanones in good to excellent yields. 4-Hydrazino-3(2H)-furanones could also be synthesized from diazo esters in excellent yields by utilising the developed strategy. We could also efficiently transform the substituted furanones to aza-prostaglandin analogues.

Keywords

• aza-prostaglandin analogue
• 3(2H)-furanone
• Mannich addition
• palladium catalysis
• tandem reaction