Synthesis of 5-alkoxy-4-amino-3-bromo-2(5H)-furanones containing benzene rings

Article abstract of DOI:10.1007/s11164-012-0674-y

Using KF as base and THF as solvent, different 5-alkoxy-3,4-dibromo-2(5H)- furanones were reacted with amines containing a benzene ring structure by Michael addition-elimination reaction at room temperature or 40 C to give twenty-three 5-alkoxy-4-amino-3-bromo-2(5H)-furanones containing benzene rings, with yields of 21-86 % (mostly over 64 %). The structures of all the newly synthesized compounds were elucidated and confirmed by FTIR, UV, ¹H NMR, ¹³C NMR, and mass spectroscopy, elemental analysis, and X-ray single-crystal diffraction. This rapid synthesis of the series of 2(5H)-furanones derivatives with different bioactive units is not only an important synthetic strategy for 2(5H)-furanone derivatives but also a basis for synthesis of potential drug molecules for activity testing.