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INTRAMOLECULAR CYCLIZATION OF 2-(HETEROARYLSULFANYL)- N-(3-OXOALKENYL)ACETAMIDES: SYNTHESIS OF 3-(HETEROARYLSULFANYL)- AND 3-SULFANYLPYRIDIN-2(1H)-ONES

Ольга А. Савченко, Вера В. Мусияк, Дмитрий С. Гончаров, Юлия П. Богза, Антон Л. Шацаускас, Валентин П. Талзи, Сергей Н. Евдокимов, Евгений Б. Ульянкин, Александр С. Фисюк
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Abstract


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.

Authors: 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*


Keywords


1,3-benzothiazole-2(3H)-thione; 3-(1,3-benzothiazol-2-ylsulfanyl)pyridin-2(1H)-one; 1,3-benzoxazole-2(3H)-thione, chloro-N-(3-oxoalkenyl)acetamides; 1-methyl-1,3-dihydro-2Н-benzimidazole-2-thione; 3-sulfanylpyridin-2(1H)-ones; intramolecular cyclization

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