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Direct esterification of amides by the dimethylsulfate-mediated activation of amide C-N bonds

文献类型：期刊论文

作者Qin, Hongjian4,5; Han, Zijian3,4; Bonku, Emmanuel Mintah2,4; Sun, Haiguo2,4; Odilov, Abdullajon2,4; Zhu, Fuqiang1; Abduahadi, Safomuddin2,4; Zhu, Weiliang3,4; Shen, Jingshan2,4; Aisa, Haji A.4,5
刊名COMMUNICATIONS CHEMISTRY
出版日期2024-04-27
卷号7期号:1页码:9
ISSN号2399-3669
DOI10.1038/s42004-024-01180-9
通讯作者Zhu, Weiliang(wlzhu@simm.ac.cn) ; Shen, Jingshan(shenjingshan@simm.ac.cn) ; Aisa, Haji A.(haji@ms.xjb.ac.cn)
英文摘要Amides are important intermediates in organic chemistry and the pharmaceutical industry, but their low reactivity requires catalysts and/or severe reaction conditions for esterification. Here, a novel approach was devised to convert amides into esters without the use of transition metals. The method effectively overcomes the inherent low reactivity of amides by employing dimethylsulfate-mediated reaction to activate the C-N bonds. To confirm the proposed reaction mechanism, control experiments and density functional theory (DFT) calculations were conducted. The method demonstrates a wide array of substrates, including amides with typical H/alkyl/aryl substitutions, N,N-disubstituted amides, amides derived from alkyl, aryl, or vinyl carboxylic acids, and even amino acid substrates with stereocentres. Furthermore, we have shown the effectiveness of dimethylsulfate in removing acyl protective groups in amino derivatives. This study presents a method that offers efficiency and cost-effectiveness in broadening the esterification capabilities of amides, thereby facilitating their increased utilization as synthetic compounds in diverse transformations. Amides are important intermediates in organic chemistry and the pharmaceutical industry, but their low reactivity requires catalysts and/or harsh reaction conditions to esterify them. Here, the authors report a versatile and mild dimethyl sulfate-mediated reaction to activate and esterify C-N bonds, achieving up to 95% amide bond cleavage.
WOS关键词CATALYZED ESTERIFICATION ; CONVERSION ; RESONANCE ; ESTERS ; FUNCTIONALIZATION ; 8-AMINOQUINOLINE ; FORMAMIDE ; CLEAVAGE ; MILD
资助项目This work was supported financially by the West Light Foundation of The Chinese Academy of Sciences (Grant No. 2018-XBYJRC-001) and Special Foundation of Chinese Academy of Sciences for strategic pilot technology (grant no. XDA12050411).[2018-XBYJRC-001] ; West Light Foundation of The Chinese Academy of Sciences[XDA12050411] ; Special Foundation of Chinese Academy of Sciences for strategic pilot technology
WOS研究方向Chemistry
语种英语
WOS记录号WOS:001209730800002
出版者NATURE PORTFOLIO
源URL[http://119.78.100.183/handle/2S10ELR8/310998]  
专题新药研究国家重点实验室
通讯作者Zhu, Weiliang; Shen, Jingshan; Aisa, Haji A.
作者单位1.Topharman Shanghai Co Ltd, Shanghai, Peoples R China
2.Chinese Acad Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, Shanghai, Peoples R China
3.Chinese Acad Sci, Shanghai Inst Mat Med, Drug Discovery & Design Ctr, CAS Key Lab Receptor Res,State Key Lab Drug Res, Shanghai, Peoples R China
4.Univ Chinese Acad Sci, Beijing, Peoples R China
5.Chinese Acad Sci, Xinjiang Tech Inst Phys & Chem, Key Lab Plant Resources & Chem Arid Reg, Urumqi, Xinjiang, Peoples R China
推荐引用方式
GB/T 7714		 Qin, Hongjian,Han, Zijian,Bonku, Emmanuel Mintah,et al. Direct esterification of amides by the dimethylsulfate-mediated activation of amide C-N bonds[J]. COMMUNICATIONS CHEMISTRY,2024,7(1):9.
APA Qin, Hongjian.,Han, Zijian.,Bonku, Emmanuel Mintah.,Sun, Haiguo.,Odilov, Abdullajon.,...&Aisa, Haji A..(2024).Direct esterification of amides by the dimethylsulfate-mediated activation of amide C-N bonds.COMMUNICATIONS CHEMISTRY,7(1),9.
MLA Qin, Hongjian,et al."Direct esterification of amides by the dimethylsulfate-mediated activation of amide C-N bonds".COMMUNICATIONS CHEMISTRY 7.1(2024):9.

入库方式： OAI收割

来源：上海药物研究所

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