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

Authors

  • Ольга А. Савченко Dostoevsky Omsk State University, 55a Mira Ave., Omsk 644077
  • Вера В. Мусияк Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi 22 / 20 Akademicheskaya St., Yekaterinburg 620108
  • Дмитрий С. Гончаров Dostoevsky Omsk State University, 55a Mira Ave., Omsk 644077
  • Юлия П. Богза Dostoevsky Omsk State University, 55a Mira Ave., Omsk 644077
  • Антон Л. Шацаускас Omsk State Technical University, 11. Mira Ave., Omsk 644050
  • Валентин П. Талзи Center of New Chemical Technologies, Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences, 54 Neftezavodskaya St., Omsk 644040
  • Сергей Н. Евдокимов Center of New Chemical Technologies, Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences, 54 Neftezavodskaya St., Omsk 644040
  • Евгений Б. Ульянкин Omsk State Technical University, 11. Mira Ave., Omsk 644050
  • Александр С. Фисюк Omsk State Technical University, 11. Mira Ave., Omsk 644050

DOI:

https://doi.org/10.1007/5674

Keywords:

1, 3-benzothiazole-2(3H)-thione, 3-(1, 3-benzothiazol-2-ylsulfanyl)pyridin-2(1H)-one, 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

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*

Author Biography

Александр С. Фисюк, Omsk State Technical University, 11. Mira Ave., Omsk 644050

Заведующий кафедрой органической химии ОмГУ им. Ф.М. Достоевского, заведующий лабораторией "Новые органические материалы" ОмГТУ, д.х.н., профессор.

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Published

2020-10-14

Issue

Vol. 56 No. 9 (2020)

Section

Original Papers