Synthesis 5-(pyrazolin-3-ylmethylidene)-2-thiohydantoins and 2-alkylsulfanyl-5-(pyrazolin-3-ylmethylidene)-3,5-dihydro-4H-imidazol-4-ones
- Authors: Vorozhtsov N.I.1, Sviridova L.A.1, Grigorkevich O.S.1, Korablina D.D.2, Beloglazkina E.K.1, Majouga A.G.1, Zyk N.V.1
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Affiliations:
- Department of Chemistry, M. V. Lomonosov Moscow State University
- Department of Fundamental Medicine, M. V. Lomonosov Moscow State University
- Issue: Vol 66, No 3 (2017)
- Pages: 506-510
- Section: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/240233
- DOI: https://doi.org/10.1007/s11172-017-1764-1
- ID: 240233
Cite item
Abstract
A reaction of 3-allyl- and 3-phenylthiohydantoins with 1,5-diphenyl- and 1-phenyl-substituted 3-formyl-2-pyrazolines was used to obtain a series of 5-(pyrazolin-3-ylmethylidene)-2-thioxotetrahydro-4H-imidazol-4-ones, the subsequent alkylation of which with methyl iodide or ethyl chloroacetate gave the corresponding 2-alkylthio-5-(pyrazolin-3-ylmethylidene)-3,5-dihydro-4H-imidazol-4-ones in the yields from 30 to 77%. The oxidation of (5Z)-3-phenyl-5-[(1,5-diphenylpyrazolin-3-yl)methylidene]-2-methylsulfanyl-4,5-dihydroimidazol-4-one with lead tetraacetate led to the corresponding pyrazole in 48% yield.
About the authors
N. I. Vorozhtsov
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: bel@org.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991
L. A. Sviridova
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: bel@org.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991
O. S. Grigorkevich
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: bel@org.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991
D. D. Korablina
Department of Fundamental Medicine, M. V. Lomonosov Moscow State University
Email: bel@org.chem.msu.ru
Russian Federation, Build. 1, 27 Lomonosovsky prosp., Moscow, 119991
E. K. Beloglazkina
Department of Chemistry, M. V. Lomonosov Moscow State University
Author for correspondence.
Email: bel@org.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991
A. G. Majouga
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: bel@org.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991
N. V. Zyk
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: bel@org.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991