[5+1]串联反应构建螺[环己酮-吡唑啉酮]骨架的研究  

Study on the Construction of Spiro[Cyclohexanone Pyrazolone]Skeleton by[5+1]Tandem Reaction

作　　者：陈治明 CHEN Zhi-ming(Guizhou Provincial Key Laboratory of Functional Materials Chemistry,School of Chemistry and Materials Science,Guizhou Normal University,Guiyang 550001,China)

机构地区：[1]贵州师范大学化学与材料科学学院贵州省功能材料化学重点实验室,贵州贵阳550001

出　　处：《化学试剂》2023年第7期152-158,共7页Chemical Reagents

基　　金：国家自然科学基金资助项目(21362006)。

摘　　要：吡唑啉酮螺环骨架的构建在新药研发领域扮演着极其重要的角色,正成为有机合成领域的研究热点之一。合成了3种具有Lewis酸和手性酰胺结构的轴手性催化剂(1a~1c),并将其应用于双苄叉丙酮与吡唑啉酮的[5+1]环加成串联反应,在室温25℃下,得到的目标化合物螺[环己酮-吡唑啉酮]的产率高(92%),对映体选择性好(89%e.e.)。该方法具有催化剂易制备、反应条件温和、对环境友好等特点,为具有生物药理活性的螺环己酮-吡唑啉酮骨架的合成提供了重要途径。The construction of pyrazolone spiro skeleton plays an extremely important role in the field of new drug research and development,and has become a research hotspot in the field of organic synthesis.Three axial chiral catalysts(1a~1c)with acidic and chiral amide structure were synthesized and applied to the[5+1]cycloaddition reaction of bisbenzylidene acetone and pyrazolone.At room temperature 25℃,the target compound was obtained in high yield(92%)and good enantioselectivity(89%e.e.).This method had the characteristics of easy preparation of catalyst,mild reaction conditions and environmental friendliness,which provided an important way for the synthesis of spirocyclohexanone-pyrazolone skeleton with biological pharmacological activity.

关 键 词：吡唑啉酮 轴手性催化剂 串联反应 [5+1]环加成 螺环己酮-吡唑啉酮 

分 类 号：O626[理学—有机化学]