酞嗪-2-二氰基甲烷鎓盐的串联环化反应及新型六环咪唑并[2,1-a]酞嗪的构建  

Cascade Cycloaddition Reaction for the Construction of Novel Hexacyclic Imidazo[2,1-a]phthalazine

作　　者：詹固 侯秋梦 韩波[1] ZHAN Gu;HOU Qiumeng;HAN Bo(State Key Laboratory of Southwestern Chinese Medicine Resources,School of Pharmacy,Chengdu University of Traditional Chinese Medicine,Chengdu 611137,China)

机构地区：[1]成都中医药大学药学院西南特色中药资源国家重点实验室,四川成都611137

出　　处：《合成化学》2022年第12期925-929,共5页Chinese Journal of Synthetic Chemistry

基　　金：四川省科技厅科技创新人才项目(2022JDRC0045);四川省应用基础研究项目(2021YJ0402);成都中医药大学杏林学者学科人才科研提升计划(BJRC2020001)。

摘　　要：酞嗪-2-二氰基甲烷鎓盐是一类研究相对较少的1,3-偶极子,目前关于其化学反应的报道主要局限于1,3-偶极环加成反应。本研究发展了一种酞嗪-2-二氰基甲烷鎓盐在1,3-偶极环加成以外的新反应模式,以酞嗪-2-二氰基甲烷鎓盐与取代2-(羟基(苯基)甲基)苯酚为原料,在质子酸的催化下经历[2+4]环加成-串联环化历程,合成了7个不同取代的六环咪唑并[2,1-a]酞嗪产物,其结构经^(1)H NMR,^(13)C NMR和HR-MS(ESI)表征。Compared with other types of 1,3-dipoles,the chemical reaction of phthalazinium-2-dicyanomethanide is much less explored.This work developed a new reaction mode of phthalazinium-2-dicyanomethanide beyond 1,3-dipole cycloadditions.Using phthalazine-2-dicyanomethane salt and substituted 2-(hydroxy(phenyl)methyl)phenol as substrates under the catalysis of protic acid,seven different substituted hexacyclic imidazo[2,1-a]phthalazine products were constructed through[2+4]cycloaddition-intramolecular cyclization.Their structures were characterized by^(1)H NMR,^(13)C NMR and HR-MS(ESI).

关 键 词：1 3-偶极 酞嗪 环加成反应 甲亚胺叶立德 杂环合成 

分 类 号：O621.3[理学—有机化学]