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Application of 1,3-disubstituted thioureas as a key synthons for the synthesis of novel 5,7-disubstituted perhydroimidazo[4,5-e][1,2,4]triazinethiones Full article

Journal Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416
Output data Year: 2025, Volume: 187, Article number : 134905, Pages count : DOI: 10.1016/j.tet.2025.134905
Authors Izmest'ev Alexei N. 1 , Romanov Nikita A. 1,2 , Streltsov Andrey A. 1 , Kolotyrkina Natalya G. 1 , Kravchenko Angelina N. 1 , Gazieva Galina A. 1
Affiliations
1 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., Moscow 119991, Russian Federation
2 D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Sq., Moscow 125047, Russian Federation

Abstract: A series of 1-alkyl-3-arylureas and thioureas, a key synthons for the synthesis of various heterocycles, have been synthesized. The corresponding 4,5-dihydroxyimidzolidin-2-ones and thiones were prepared from (thio)ureas with glyoxal, and the selectivity of their reaction with thiosemicarbazide was studied. Regioisomeric 7-alkyl-5-aryl- and 5-alkyl-7-aryl-3-thioxoperhydroimidazo[4,5-e][1,2,4]triazin-6-ones(thiones) were prepared and separated by fractional crystallization. Intermediate 3-alkyl-2-(1-(4-chlorophenyl)-5-ethoxy-2-oxoimidazolidin-4-yl)hydrazinecarbothioamides were also isolated. The structures of the regioisomers and intermediates were unambiguously determined by two-dimensional NMR NOESY spectral data and X-ray diffraction studies.
Cite: Izmest'ev A.N. , Romanov N.A. , Streltsov A.A. , Kolotyrkina N.G. , Kravchenko A.N. , Gazieva G.A.
Application of 1,3-disubstituted thioureas as a key synthons for the synthesis of novel 5,7-disubstituted perhydroimidazo[4,5-e][1,2,4]triazinethiones
Tetrahedron. 2025. V.187. 134905 . DOI: 10.1016/j.tet.2025.134905 WOS Scopus OpenAlex
Identifiers:
≡ Web of science: WOS:001566590500003
≡ Scopus: 2-s2.0-105014805846
≡ OpenAlex: W4413640837
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