硫代丁内酯拼接吡唑啉酮双螺环化合物的合成  

Synthesis of Novel Bispiro[pyrazolone-thiobutyrolactone]Derivatives

作　　者：姜维艳 游原 刘仁明 张敏[3] 刘雄利[3] 彭礼军[3] JIANG Weiyan;YOU Yuan;LIU Renming;ZHANG Min;LIU Xiongli;PENG Lijun(Guizhou Equipmet Manufacturing Vocational College,Guiyang 550025,China;Hunan First Normal University,Changsha 410205,China;National&Local Joint Engineering Research Center for the Exploitaion of Homology Resources of Medicine and Food,Guizhou University,Guiyang 550025,China)

机构地区：[1]贵州装备制造职业学院,贵州贵阳550025 [2]湖南第一师范学院,湖南长沙410205 [3]贵州大学西南药食两用资源开发利用技术国家地方联合工程研究中心,贵州贵阳550025

出　　处：《合成化学》2022年第8期649-653,共5页Chinese Journal of Synthetic Chemistry

基　　金：贵大培育项目(202078)。

摘　　要：以3-异硫氰酸酯取代的硫代丁内酯1为合成子,在有机催化剂DABCO作用下,与各种取代的吡唑啉酮烯烃2发生Michael加成与环化反应,获得了9个未见文献报道的新型硫代丁内酯拼接吡唑啉酮双螺环化合物3a~3i,产率70%~77%,dr 2/1~9/1,其结构经^(1)H NMR,^(13)C NMR和HR-MS(ESI-TOF)表征,通过单晶进一步确定了化合物3c的构型。该类化合物含有螺环丁内酯和螺环吡唑啉酮生物活性骨架,对医药行业具有重要的潜在价值。In this paper,3isothiocyanato thiobutyrolactone 1 and various alkylidene pyrazolones 2 were used as raw materials,the Michael/cyclization reaction occurred.Nine novel bispiro[pyrazolone-thiobutyrolactone]derivatives 3a~3i were obtained.The yields and dr of 3a~3i were 70%~77%and 2/1~9/1,respectively.The structures of products 3 were characterized by ^(1)H NMR,^(13)C NMR and HR-MS(ESI-TOF).The configuration of compound 3c was further determined by single crystals.These compounds contain two potential bioactive skeletons of spiropyrazolone and spirothiobutyrolactone,which has important potential value for the pharmaceutical industry.

关 键 词：3-异硫氰酸酯取代的硫代丁内酯 吡唑啉酮烯烃 Michael加成与环化反应 硫代丁内酯拼接吡唑啉酮双螺环化合物 合成 

分 类 号：O626.13[理学—有机化学] O623.7[理学—化学]