DBU催化2-氟烷基咪唑的合成及其功能化  

DBU-Catalyzed Synthesis of 2-Fluoroalkyl Imidazole and Its Functionalization

作　　者：张家荣 李珊[1,2] 杨勇健 雷婷婷 杜如莎 冼丽清 ZHANG Jia-rong;LI Shan;YANG Yong-jian;LEI Ting-ting;DU Ru-sha;XIAN Li-qing(Key Laboratory of Regional Ecological Environment Analysis and Pollution Control of West Guangxi,Baise University,Baise 533000,China;School of Chemistry and Environment Engineering,Baise University,Baise 533000,China;School of Materials Science and Engineering,Baise University,Baise 533000,China)

机构地区：[1]百色学院桂西区域生态环境分析和污染控制重点实验室,广西百色533000 [2]百色学院化学与环境工程学院,广西百色533000 [3]百色学院材料科学与工程学院,广西百色533000

出　　处：《化学试剂》2021年第11期1595-1603,共9页Chemical Reagents

基　　金：广西自然科学基金项目(2017GXNSFBA198225);广西高校中青年教师基础能力提升项目(2017KY0719);广西高校重点学科-材料物理与化学项目(080501);广西区级大学生创新创业训练项目(202010609083)。

摘　　要：含氟咪唑类化合物的合成方法进展十分缓慢,限制了其在医药、农药等领域中的应用。以20 mol%1,8-二氮杂二环十一碳-7-烯(DBU)为催化剂,含氟炔丙基脒在乙腈中60℃空气条件下通过5-exo-dig关环反应以中等至优秀的产率生成2-氟烷基-5-甲基咪唑。2-氟烷基-5-甲基咪唑被二氧化硒氧化生成2-氟烷基咪唑-5-甲醛,提高了产物的反应活性,并进一步尝试了其与邻苯二胺的反应,合成了2-氟烷基咪唑联苯并咪唑化合物。以上反应体系简单、操作简便,可实现大剂量2-氟烷基咪唑类化合物的合成,丰富了含氟咪唑的化合物库,推动含氟咪唑在各个领域中的应用。The number of biologically active pharmaceuticals and agrochemicals containing fluorinated imidazole motif was still surprisingly limited due to lack of efficient methods.20 mol%DBU was used as the catalyst,converted fluorinated propargyl amidineto 2-fluoroalkyl-5-methyl imidazole in CH 3CN at 60℃under air by 5-exo-dig cyclization in moderate to excellent yields.In order to functionalize the product,2-fluoroalkyl imidazole-5-carbaldehydes were obtained by oxidation of SeO 2,which could react with o-phenylenediamines to give 2-fluoroalkyl imidazole-benzimidazoles.These simple and easy operationally reactions could be used to realize large scale synthesis of 2-fluoroalkyl imidazoles,enriching the library of fluorinated imidazole-containing compounds and promoting the application of fluorinated imidazoles in various fields.

关 键 词：含氟炔丙基脒 DBU催化 2-氟烷基咪唑 关环反应 功能化 

分 类 号：O627.7[理学—有机化学]