2,5-和 4,5-取代噻唑的区域选择性合成——通过异氰与 2-氧代-2-(氨基)乙二硫代酸酯的环化反应。
The regioselective synthesis of 2,5- and 4,5-disubstituted thiazoles the cyclization of 2-oxo-2-(amino)ethanedithioates with isocyanides.
机构信息
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru - 570 006, India.
Department of Studies in Organic Chemistry, University of Mysore, Manasagangotri, Mysuru - 570 006, India.
出版信息
Org Biomol Chem. 2022 Jul 27;20(29):5771-5778. doi: 10.1039/d2ob00837h.
The regioselective synthesis of 2-(methylthio)--aryl/alkylthiazole-5-carboxamides and ethyl-5-(aryl/alkyl carbamoyl)thiazole-4-carboxylates was carried out the base-induced cyclization of methyl-2-oxo-2-(amino)ethanedithioates with TosMIC and ethyl isocyanoacetate, respectively, with high yields. The regioisomeric products were confirmed based on X-ray diffraction studies. An advantage of the present method is the wide-ranging isocyanide reactivity compared to earlier protocols, while the catalyst-free nature and rapid reaction times are noteworthy features.
通过甲氧基碘苯（TosMIC）和氰基乙酸乙酯分别诱导 2-氧代-2-（氨基）乙二硫代酸甲酯和乙基异氰基乙酸酯的基诱导环化反应，可以高产率地合成 2-（甲硫基）-芳基/烷基噻唑-5-甲酰胺和 5-（芳基/烷基氨基甲酰基）噻唑-4-羧酸乙酯。基于 X 射线衍射研究确定了区域异构体产物。与早期方案相比，本方法的一个优点是异氰化物的反应活性范围更广，而无催化剂和快速反应时间则是其显著特点。
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