Intramolecular cyclization of 2-(heteroarylsulfanyl)-N-(3-oxoalkenyl)acetamides: synthesis of 3-(heteroarylsulfanyl)- and 3-sulfanylpyridin-2(1H)-ones

• Published in: Chemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 56; no. 9; pp. 1180 - 1186
• Main Authors: Savchenko, Olga А., Musiyak, Vera V., Goncharov, Dmitry S., Bogza, Yulia P., Shatsauskas, Anton L., Talzi, Valentin P., Evdokimov, Sergey N., Ulyankin, Evgeny B., Fisyuk, Alexander S.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01-09-2020; Springer Nature B.V
• Subjects: Acetic acid; Alkylation; Bromination; Chemistry; Chemistry and Materials Science; Nitration; Organic Chemistry; Pharmacy; 3-(1,3-benzothiazol-2-ylsulfanyl)pyridin-2; 1-methyl-1,3-dihydro-2; (3-oxoalkenyl)acetamides; intramolecular cyclization; one; 1,3-benzoxazole-2; 1,3-benzothiazole-2; chloro; 3-sulfanylpyridin-2; ones; thione; benzimidazole-2-thione
• ISSN: 0009-3122; 1573-8353
• DOI: 10.1007/s10593-020-02795-1

The reaction of 2-chloro-
N
-(3-oxoalkenyl)acetamides with 1,3-benzothiazole-2(3
H
)-thione, 1,3-benzoxazole-2(3
H
)-thione, and 1-methyl-1,3-dihydro-2
H
-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(1
H
)-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(1
H
)-ones have been studied. The action of zinc in acetic acid transformed these compounds into 3-sulfanylpyridin-2(1
H
)-ones.