通过三氟甲基亚胺基亚砜叶立德与硫氰酸钠的插入/环化反应合成-α-芳基-4-三氟甲基噻唑-2-胺
Synthesis of -Aryl-4-trifluoromethylthiazol-2-amines via Insertion/Annulation of Trifluoromethylimidoyl Sulfoxonium Ylides with Sodium Thiocyanate.
作者信息
Ding Yuhao, Liu Yaopeng, Ge Jin, Wu Xi, Li Zhenghao, Cheng Guolin
机构信息
Xiamen Key Laboratory of Optoelectronic Materials and Advanced Manufacturing, College of Materials Science and Engineering, Huaqiao University, Xiamen 361021, China.
Key Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education, Jiangxi Normal University, Nanchang 330022, China.
出版信息
J Org Chem. 2024 Sep 6;89(17):12255-12262. doi: 10.1021/acs.joc.4c01199. Epub 2024 Aug 16.
An efficient -TsOH-mediated insertion of sodium thiocyanate into trifluoromethylimidoyl sulfoxonium ylides has been reported, affording annulated -aryl-4-trifluoromethylthiazol-2-amines in 42-84% yields in a one-pot manner. This protocol encompasses a variety of trifluoromethylimidoyl sulfoxonium ylides with thiocyanate serving as the source of the "S-C═N" moiety of the thiazole ring. The versatile transformations of the resulting pharmacologically important -aryl-4-trifluoromethylthiazol-2-amines were also demonstrated.
据报道，在对甲苯磺酸（-TsOH）介导下，硫氰酸钠可高效插入三氟甲基亚胺基亚砜叶立德中，以一锅法得到环化的-芳基-4-三氟甲基噻唑-2-胺，产率为42%-84%。该方案涵盖了多种三氟甲基亚胺基亚砜叶立德，硫氰酸盐作为噻唑环“S-C═N”部分的来源。还展示了所得具有重要药理活性的-芳基-4-三氟甲基噻唑-2-胺的多种转化反应。
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