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

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...

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Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2020-09, Vol.56 (9), p.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: Article
Language:English
Subjects:
Acetic acid
Alkylation
Bromination
Chemistry
Chemistry and Materials Science
Nitration
Organic Chemistry
Pharmacy
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Summary: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.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-020-02795-1