Synthesis of N-[5-alkoxy-2(5H)-furanonyl] amino acid propargyl esters

Article abstract of DOI:10.1007/s11164-011-0429-1

Using K₂CO₃ as a base and CH₃CN as solvent, different kinds of N-[5-alkoxy-2(5H)-furanonyl] amino acids were reacted with propargyl bromide via substitution reaction at 40 °C to give 16 N-[5-alkoxy-2(5H)-furanonyl] amino acid propargyl esters with the yields of 44-85% (mostly over 74%). The structures of all newly synthesized compounds were elucidated and confirmed by FTIR, UV, ¹H NMR, C NMR, MS, and elemental analysis. The rapid, efficient, and brief synthesis of the series propargyl esters with multiple bioactive units, will afford not only a basis for the activity test of potential drug molecules, but also an important synthetic strategy for 2(5H)-furanone derivatives with polyfunctional groups. Springer Science+Business Media B.V. 2011.