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

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.
Source :
Chemistry of Heterocyclic Compounds. Sep2020, Vol. 56 Issue 9, p1180-1186. 7p.
Publication Year :
2020

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. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
00093122
Volume :
56
Issue :
9
Database :
Academic Search Index
Journal :
Chemistry of Heterocyclic Compounds
Publication Type :
Academic Journal
Accession number :
146952193
Full Text :
https://doi.org/10.1007/s10593-020-02795-1