First Synthesis of 3-Acetyl-2-aminothiophenes Using the Gewald Reaction

Abstract

Novel 3-acetyl-2-aminothiophenes were prepared from cyanoacetone and1,4-dithianyl-2,5-diols using a modified Gewald reaction. The syntheses of thecorresponding acetamides, as well as that of 3-acetyl-2-amino-5-nitrothiophene – aninteresting building-block for thiophene azo dyes – are reported. Detailed spectroscopicinvestigations (1H-NMR, 13C-NMR, MS, IR) of the obtained compounds are presented.

Keywords

• Gewald reaction
• Thiophene synthesis
• Cyclization
• Condensation.