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Intramolecular cyclization of 2-(heteroarylsulfanyl)- N -(3-oxoalkenyl)acetamides: synthesis of 3-(heteroarylsulfanyl)- and 3-sulfanylpyridin-2(1 H )-ones
Chemistry of Heterocyclic Compounds ( IF 1.4 ) Pub Date : 2020-10-17 , DOI: 10.1007/s10593-020-02795-1
Olga А. Savchenko , Vera V. Musiyak , Dmitry S. Goncharov , Yulia P. Bogza , Anton L. Shatsauskas , Valentin P. Talzi , Sergey N. Evdokimov , Evgeny B. Ulyankin , Alexander S. Fisyuk

The reaction of 2-chloro-N-(3-oxoalkenyl)acetamides with 1,3-benzothiazole-2(3H)-thione, 1,3-benzoxazole-2(3H)-thione, and 1-methyl-1,3-dihydro-2H-benzimidazole-2-thione led to the formation of 2-(heteroarylsulfanyl)-N-(3-oxoalkenyl)acetamides. By the action of a base, these compounds were converted into pyridin-2(1H)-ones containing a divalent sulfur atom in position C-3 bonded to a heterocyclic ring. Bromination, nitration, alkylation of 3-(1,3-benzothiazol-2-ylsulfanyl)pyridin-2(1H)-ones have been studied. The action of zinc in acetic acid transformed these compounds into 3-sulfanylpyridin-2(1H)-ones.



中文翻译:

2-(杂芳基硫烷基)-N-(3-氧代烯基)乙酰胺的分子内环化:3-(杂芳基硫烷基)-和3-硫烷基吡啶-2(1 H)-一的合成

2-氯-N-(3-氧代烯基)乙酰胺与1,3-苯并噻唑-2(3 H)-硫酮,1,3-苯并恶唑-2(3 H)-硫酮和1-甲基-1的反应,3-二氢-2 H-苯并咪唑-2-硫酮导致形成2-(杂芳基硫烷基)-N-(3-氧代烯基)乙酰胺。在碱的作用下,这些化合物被转化为在与杂环键合的C-3位上含有二价硫原子的吡啶-2(1 H)-1 。已经研究了3-(1,3-苯并噻唑-2-基硫烷基)吡啶-2(1 H)-一的溴化,硝化和烷基化。锌在乙酸中的作用将这些化合物转化为3-硫烷基吡啶2-2(1 H)-one。

更新日期:2020-10-17
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