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Synthesis of CF3-Containing 2-Imidazolines and Imidazoles via a Iodide-Promoted [3+2] Cyclization Reaction

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成果类型:
期刊论文
作者:
Wang, Huamin*;Niu, Wenjing;He, Yongjun;Wei, Yibo;Li, Xianxian;...
通讯作者:
Wang, Huamin;Lin, YW
作者机构:
[Wang, Huamin; Niu, Wenjing; He, Yongjun; Wei, Yibo; Li, Xianxian; Lin, Ying-Wu; Wang, HM] Univ South China, Sch Chem & Chem Engn, Hengyang 421001, Peoples R China.
[Lin, Ying-Wu] Univ South China, Hengyang Med Coll, Hengyang 421001, Peoples R China.
[Lin, Ying-Wu] Univ South China, Med Sch, Lab Prot Struct & Funct, Hengyang 421001, Peoples R China.
通讯机构:
[Lin, YW ; Wang, HM] U
Univ South China, Sch Chem & Chem Engn, Hengyang 421001, Peoples R China.
Univ South China, Hengyang Med Coll, Hengyang 421001, Peoples R China.
Univ South China, Med Sch, Lab Prot Struct & Funct, Hengyang 421001, Peoples R China.
语种:
英文
期刊:
JOURNAL OF ORGANIC CHEMISTRY
ISSN:
0022-3263
年:
2023
卷:
88
期:
21
页码:
15282-15287
基金类别:
National Natural Science Foundation of China [21977042]; Hunan Provincial Natural Science Foundation of China [2022JJ40362]; Scientific Research Fund of Hunan Education Department, China [22A0284]
机构署名:
本校为第一且通讯机构
院系归属:
化学化工学院
医学院
摘要:
We report herein a general and effective system achieving cyclization of β-trifluoromethyl enones with amidines in the presence of 1,3-diiodo-5,5-dimethylhydantoin (DIH), which affords a range of trifluoromethylated 2-imidazolines in synthetically useful yields with good diastereoselectivities (up to 95% yield, up to 98:2 dr) and good functional group tolerance. Furthermore, the one-pot synthesis of trifluoromethylated imidazoles via sequential cyclization and oxidation is demonstrated. More significantly, the reaction mechanism was verified b...

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