Intramolecular cyclization of 2-(heteroarylsulfanyl)-N-(3-oxoalkenyl)acetamides: synthesis of 3-(heteroarylsulfanyl)- and 3-sulfanylpyridin-2(1H)-ones Full article
Journal |
Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353 |
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Output data | Year: 2020, Volume: 56, Number: 9, Pages: 1180-1186 Pages count : 7 | ||||||||
Tags | 1,3-benzothiazole-2(3H)-thione, 3-(1,3-benzothiazol-2-ylsulfanyl)pyridin-2(1H)-one, 1,3-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 | ||||||||
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Affiliations |
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Funding (1)
1 | Russian Foundation for Basic Research | 19-13-00273 |
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.
Cite:
Savchenko O.А.
, Musiyak V.V.
, Goncharov D.S.
, Bogza Y.P.
, Shatsauskas A.L.
, Talzi V.P.
, Evdokimov S.N.
, Ulyankin E.B.
, Fisyuk A.S.
Intramolecular cyclization of 2-(heteroarylsulfanyl)-N-(3-oxoalkenyl)acetamides: synthesis of 3-(heteroarylsulfanyl)- and 3-sulfanylpyridin-2(1H)-ones
Chemistry of Heterocyclic Compounds. 2020. V.56. N9. P.1180-1186. WOS Scopus РИНЦ
Intramolecular cyclization of 2-(heteroarylsulfanyl)-N-(3-oxoalkenyl)acetamides: synthesis of 3-(heteroarylsulfanyl)- and 3-sulfanylpyridin-2(1H)-ones
Chemistry of Heterocyclic Compounds. 2020. V.56. N9. P.1180-1186. WOS Scopus РИНЦ
Original:
Савченко О.А.
, Мусияк В.В.
, Гончаров Д.С.
, Богза Ю.П.
, Шацаускас А.Л.
, Талзи В.П.
, Евдокимов С.Н.
, Ульянкин Е.Б.
, Фисюк А.С.
Внутримолекулярная циклизация 2-(гетероарилсульфанил)-N-(3-оксоалкенил)ацетамидов: синтез 3-(гетероарилсульфанил)-и 3-сульфанилпиридин-2(1Н)-онов
Химия гетероциклических соединений. 2020. Т.56. №9. С.1180-1186.
Внутримолекулярная циклизация 2-(гетероарилсульфанил)-N-(3-оксоалкенил)ацетамидов: синтез 3-(гетероарилсульфанил)-и 3-сульфанилпиридин-2(1Н)-онов
Химия гетероциклических соединений. 2020. Т.56. №9. С.1180-1186.
Dates:
Submitted: | Mar 15, 2020 |
Accepted: | Apr 17, 2020 |
Identifiers:
Web of science | WOS:000579237000002 |
Scopus | 2-s2.0-85092623017 |
Elibrary | 45257024 |