Kozminykh V O, Igidov N M, Kozminykh E N, Aliev Z G
Laboratory for the Synthesis of Biological Active Compounds, Perm Pharmaceutical Institute, Russia.
Pharmazie. 1993 Feb;48(2):99-106.
The Wittig reaction of 5-aryl-furan-2,3-diones 1 with acylmethylenetriphenylphosphoranes 2 conducted by heating under reflux in benzene solutions, proceeded regiospecifically to afford 2-acylmethylene-5-aryl-3(2H)-furanones 5 in good yields. When the starting compounds 1 and 2 were allowed to react at room temperature, the stable intermediate 5-aryl-2-hydroxy-2-triphenylphosphoranylidenemethyl-3(2H)-furanone s 15 were yielded. The latter adducts underwent triphenylphosphine oxide elimination on heating to form the same olefins 5. The structural assignments of the synthesized compounds were made on the basis of their spectral data and X-ray analysis for 5a. Some of the compounds obtained exhibit antimicrobial activity and one compound of the 3(2H)-furanone series exhibited anticonvulsant activity.
5-芳基-呋喃-2,3-二酮1与酰基亚甲基三苯基膦2在苯溶液中回流加热进行维蒂希反应，区域专一性地生成2-酰基亚甲基-5-芳基-3(2H)-呋喃酮5，产率良好。当起始化合物1和2在室温下反应时，生成稳定的中间体5-芳基-2-羟基-2-三苯基膦亚基甲基-3(2H)-呋喃酮15。后者的加合物加热时发生三苯基氧膦消除反应，形成相同的烯烃5。合成化合物的结构归属基于其光谱数据以及对5a的X射线分析。所得到的一些化合物具有抗菌活性，并且3(2H)-呋喃酮系列中的一个化合物具有抗惊厥活性。
