CAJ | 학술논문

3-脱氢莽草酸甲酯与丙二腈、氰乙酸乙酯及氰乙酸甲酯等活性亚甲基化合物在一定条件下发生缩合、芳构化及环合反应,可方便地构建C—C键并得到多取代的2-氨基苯并呋喃类化合物(3a~3e,4a和4b),其中化合物3a中的氰基和甲氧羰基可分别进行选择性水解。该方法具有原料易得、条件温和、操作简单及收率高等优点,为可再生生物质资源莽草酸的多样化转化和利用提供了新思路。
3-탈경망초산갑지여병이정、청을산을지급청을산갑지등활성아갑기화합물재일정조건하발생축합、방구화급배합반응,가방편지구건C—C건병득도다취대적2-안기분병부남류화합물(3a~3e,4a화4b),기중화합물3a중적청기화갑양탄기가분별진행선택성수해。해방법구유원료역득、조건온화、조작간단급수솔고등우점,위가재생생물질자원망초산적다양화전화화이용제공료신사로。
With the diminishing of fossil oil reserves, chemical conversion and value-added utilization of re-newable 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 1 H NMR, 13 C 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.