碘化亚铜催化5-乙炔基噁唑-2,4二酮与苯甲酰乙腈的脱羧[3+2]环加成反应  

CuI-catalyzed Decarboxylative[3+2]Cycloaddition of Ethynylethylene Cyclic Carbamates with Azlactones

作　　者：包庆 王浩宇 金鑫 葛真真 周鸣强 赵建强 陈永正 袁伟成 BAO Qing;WANG Haoyu;JIN Xin;GE Zhenzhen;ZHOU Mingqiang;ZHAO Jianqiang;CHEN Yongzheng;YUAN Weicheng(College of Pharmacy,Zunyi Medical University,Key Laboratory of Biocatalysis and Chiral Drug Synthesis of Guizhou Province,Zunyi 563000,China;Chengdu Likai Chiral Tech Co.,Ltd.,National Engineering Research Center of Chiral Drugs,Chengdu 610041,China;Chengdu Institute of Organic Chemistry,Chinese Academy of Sciences,Chengdu,610041,China;Zhejiang Jinhua Conba Bio-Pharm.Co.,Ltd.Jinhua 321016,China)

机构地区：[1]遵义医科大学药学院贵州省生物催化与手性药物合成重点实验室,贵州遵义563000 [2]成都丽凯手性技术有限公司,手性药物国家工程研究中心,四川成都610041 [3]中国科学院成都有机化学有限公司,四川成都610041 [4]浙江金华康恩贝生物制药有限公司,浙江金华321016

出　　处：《合成化学》2023年第6期429-435,共7页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(22171029,21901024,21871252,21801024,21801026)。

摘　　要：2,3-二氢呋喃类化合物是一类重要的杂环化合物,广泛存在于天然产物中,同时也是合成手性四氢呋喃化合物的重要前体,发展新颖简单的方法来合成这一类化合物具有重要意义。以5-乙炔基噁唑-2,4二酮和芳基甲酰乙腈为原料,在金属碘化亚铜的催化下发生脱羧[3+2]环加成反应,合成了13个结构新颖的二氢呋喃类化合物3a~3m,收率82%~99%,并对这些化合物进行了^(1)H NMR、^(13)C NMR和HR-MS(ESI-TOF)表征。2,3-Dihydrofurans are an important class of heterocyclic compounds that are widely found in natural products and are also important precursors for the synthesis of chiral tetrahydrofuran compounds.The development of novel and simple methods for the synthesis of this class of compounds is still of great importance.In this paper,2,3-dihydrofuran derivatives 3a~3m with diverse structure were obtained with yield of 82%~99%by CuI-catalyzed decarboxylation[3+2]cycloaddition of 5-ethynyloxazole-2,4-diones with arylacetonitriles.Meanwhile,these compounds were characterized by ^(1)H NMR,^(13)C NMR,and HR-MS(ESI-TOF).

关 键 词：5-乙炔基噁唑-2 4二酮 苯甲酰乙腈 金属催化 脱羧环加成 2 3-二氢呋喃类化合物 合成 乙炔基环状化合物 

分 类 号：O626[理学—有机化学]