Intramolecular cyclization of 2-(heteroarylsulfanyl)- N -(3-oxoalkenyl)acetamides: synthesis of 3-(heteroarylsulfanyl)-
- PDF / 329,407 Bytes
- 7 Pages / 594 x 792 pts Page_size
- 32 Downloads / 151 Views
Intramolecular cyclization of 2-(heteroarylsulfanyl)N-(3-oxoalkenyl)acetamides: synthesis of 3-(heteroarylsulfanyl)and 3-sulfanylpyridin-2(1H)-ones Olga А. Savchenko1, Vera V. Musiyak2, Dmitry S. Goncharov1, Yulia P. Bogza1, Anton L. Shatsauskas3, Valentin P. Talzi4, Sergey N. Evdokimov4, Evgeny B. Ulyankin3, Alexander S. Fisyuk3* 1
Dostoevsky Omsk State University, 55a Mira Ave., Omsk 644077, Russia 2 Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi 22 / 20 Akademicheskaya St., Yekaterinburg 620108, Russia . 3 Omsk State Technical University, 11. Mira Ave., Omsk 644050, Russia; e-mail: [email protected] 4 Center of New Chemical Technologies, Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences, 54 Neftezavodskaya St., Omsk 644040, Russia Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(9), 1180–1186
Submitted March 15, 2020 Accepted April 17, 2020
The reaction of 2-chloro-N-(3-oxoalkenyl)acetamides with 1,3-benzothiazole-2(3H)-thione, 1,3-benzoxazole-2(3H)-thione, and 1-methyl1,3-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. Keywords: 1,3-benzothiazole-2(3H)-thione, 3-(1,3-benzothiazol-2-ylsulfanyl)pyridin-2(1H)-one, 1,3-benzoxazole-2(3H)-thione, chloroN-(3-oxoalkenyl)acetamides, 1-methyl-1,3-dihydro-2Н-benzimidazole-2-thione, 3-sulfanylpyridin-2(1H)-ones, intramolecular cyclization.
There are few known methods for the synthesis of 3-sulfanylpyridin-2(1H)-ones. They are based on the transformations of thiazolo[4,5-b]pyridines1 or the introduction of a thio group via diazonium salts obtained from the hard to access 3-amino-2-methoxypyridines.2 3-Sulfanylpyridin-2(1H)-ones and 3-sulfanylquinolin-2(1H)-ones are used for the synthesis of 2-pyridones or 2-quinolones containing a divalent sulfur atom at the C-3 position bonded to alkyl, aryl groups, or a heterocyclic ring.2–9 Interest in such compounds is primarily owed to their biological activity.10–19 Among them, compounds that are effective in the treatment of erectile dysfunction,3–6 cancers,7,8 possess antiviral activity9 including antiHIV,2,20 exhibit the properties of cannabinoid receptor antagonists21 were found. We proposed a strategy22 for the synthesis of 3-substituted pyridin-2(1H)-ones and their hydrogenated deriva0009-3122/20/56(9)-1180©2020 Springer Science+Business Media, LLC
tives based on nucleophilic substitution of halogen in 2-chloro-N-(3-oxoalkenyl)- or 2-chloro-N-(3-oxoalkyl)acetamides by a functional group with subsequent intramolecular cyclization of the resulting intermediate. This strategy makes it possible on t
Data Loading...
