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Synthesis of a novel family of water-soluble 2H,3H-[1,3]thia- and -selenazolo[3,2-a]pyridin-4-ium heterocycles by annulation reactions
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2019-01-02 , DOI: 10.1016/j.tetlet.2019.01.001
Vladimir A. Potapov , Roman S. Ishigeev , Svetlana V. Amosova , Tatyana N. Borodina

Regioselective synthesis of a novel family of water-soluble 2H,3H-[1,3]chalcogenazolo[3,2-a]pyridin-4-ium derivatives was developed based on 2-pyridinesulfenyl and -selenenyl halides and unsaturated compounds. The annulation reactions with divinyl sulfide, selenide and N-vinylpyrrolidin-2-one led to addition of the chalcogen atom to the terminal carbon of the double bond whereas the reaction with tetravinylsilane proceeded with opposite regiochemistry. Tricyclic condensed heterocycles were obtained from 2,3-dihydrofuran and cycloalkenes. The products represent novel promising scaffolds for organic synthesis and possible drug discovery.



中文翻译:

通过环化反应合成新型的水溶性2 H,3 H- [1,3]硫杂-和-硒唑并[3,2 - a ]吡啶-4-鎓杂环族

基于2-吡啶硫基和-硒烯基卤化物和不饱和化合物,开发了一种新型的水溶性2 H,3 H- [1,3]硫族lc唑[3,2 - a ]吡啶-4-鎓衍生物的区域选择性合成。与二乙烯基硫化物,硒化物和N-乙烯基吡咯烷酮-2-酮的环化反应导致将硫族元素原子加到双键的末端碳上,而与四乙烯基硅烷的反应则以相反的区域化学进行。从2,3-二氢呋喃和环烯烃获得三环稠合杂环。该产品代表了用于有机合成和可能的药物发现的新型有前途的支架。

更新日期:2019-01-02
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