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Synthetic approaches to fluorinated derivatives of 4-(vinylthio)pyridine
Journal of Fluorine Chemistry ( IF 1.7 ) Pub Date : 2022-11-28 , DOI: 10.1016/j.jfluchem.2022.110063
Larisa Politanskaya , Bulat Khasanov , Alexander Potapov

An effective strategy for the synthesis of new polyfluoropyridine derivatives, which are valuable building blocks in the synthesis of potentially biologically active fluorine-containing compounds, has been developed. A series of fluorinated derivatives of 4-(vinylthio)pyridine have been synthesized, starting from pentafluoropyridine and 2-mercaptoethanol via aromatic nucleophilic substitution of fluorine atoms and elimination process. The obtained derivatives with NHAlk-substituents at position 2-, are of interest as new heteroaryl vinyl sulfide components that can be used in the synthesis of more complex fluorine-containing structures. The possibility of oxidation of tetrafluoro-4-(vinylthio)pyridine to the corresponding heteroaryl vinyl sulfone has been demonstrated. It was found that the resulting tetrafluoro-4-(vinylsulfonyl)pyridine reacted with cycloheptanamine under basic conditions to form a heterocyclic framework containing fragments of pyridine and 3,4-dihydro-2H-1,4-thiazine 1,1-dioxide.



中文翻译:

4-(乙烯硫基)吡啶氟化衍生物的合成方法

已经开发出一种合成新型多氟吡啶衍生物的有效策略,这些衍生物是合成具有潜在生物活性的含氟化合物的重要组成部分。以五氟吡啶和2-巯基乙醇为原料,通过氟原子的芳香亲核取代和消除过程,合成了一系列4-(乙烯硫基)吡啶的氟化衍生物。所获得的在 2- 位具有 NHAlk-取代基的衍生物作为新的杂芳基乙烯基硫醚组分令人感兴趣,可用于合成更复杂的含氟结构。四氟-4-(乙烯基硫基)吡啶氧化成相应的杂芳基乙烯基砜的可能性已经得到证实。H -1,4-噻嗪 1,1-二氧化物。

更新日期:2022-12-01
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