丙二腈及氰乙酸酯参与的3-脱氢莽草酸甲酯缩合-芳构化-环合串联反应

With the diminishing of fossil oil reserves, chemical conversion and value-added utilization of renewable biomass have become a worldwide topic for chemists. It was demonstrated that the reaction between (-)-methyl 3-dehydroshikimate (3-MDHS) and several active methylene compounds under facile conditions gave rise to substituted 2-aminobenzofurans in moderate to good yields. The process involved the formation of a new C-C bond through condensation, followed by a sequential aromatization/cyclization reaction. The chemoselective hydrolysis of compound 3a was also realized. The structures of the synthesized compounds were characterized by H-1 NMR, C-13 NMR, MS and IR. The ready availability of biosourced starting materials, the convenient reaction conditions as well as the easy workup procedures made this protocol a practical method for the chemical conversion of the renewable biomass (-)-shikimic acid.