Synthesis 5-(pyrazolin-3-ylmethylidene)-2-thiohydantoins and 2-alkylsulfanyl-5-(pyrazolin-3-ylmethylidene)-3,5-dihydro-4H-imidazol-4-ones
N I Vorozhtsov
1
,
L.A. Sviridova
1
,
O S Grigorkevich
1
,
D D Korablina
2
,
E K Beloglazkina
1
,
A G Majouga
1
,
N. V. Zyk
1
Publication type: Journal Article
Publication date: 2017-03-01
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
General Chemistry
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.
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Vorozhtsov N. I. et al. Synthesis 5-(pyrazolin-3-ylmethylidene)-2-thiohydantoins and 2-alkylsulfanyl-5-(pyrazolin-3-ylmethylidene)-3,5-dihydro-4H-imidazol-4-ones // Russian Chemical Bulletin. 2017. Vol. 66. No. 3. pp. 506-510.
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Vorozhtsov N. I., Sviridova L., Grigorkevich O. S., Korablina D. D., Beloglazkina E. K., Majouga A. G., Zyk N. V. Synthesis 5-(pyrazolin-3-ylmethylidene)-2-thiohydantoins and 2-alkylsulfanyl-5-(pyrazolin-3-ylmethylidene)-3,5-dihydro-4H-imidazol-4-ones // Russian Chemical Bulletin. 2017. Vol. 66. No. 3. pp. 506-510.
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TY - JOUR
DO - 10.1007/s11172-017-1764-1
UR - http://link.springer.com/10.1007/s11172-017-1764-1
TI - Synthesis 5-(pyrazolin-3-ylmethylidene)-2-thiohydantoins and 2-alkylsulfanyl-5-(pyrazolin-3-ylmethylidene)-3,5-dihydro-4H-imidazol-4-ones
T2 - Russian Chemical Bulletin
AU - Vorozhtsov, N I
AU - Sviridova, L.A.
AU - Grigorkevich, O S
AU - Korablina, D D
AU - Beloglazkina, E K
AU - Majouga, A G
AU - Zyk, N. V.
PY - 2017
DA - 2017/03/01
PB - Springer Nature
SP - 506-510
IS - 3
VL - 66
SN - 1066-5285
SN - 1573-9171
ER -
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BibTex (up to 50 authors)
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@article{2017_Vorozhtsov,
author = {N I Vorozhtsov and L.A. Sviridova and O S Grigorkevich and D D Korablina and E K Beloglazkina and A G Majouga and N. V. Zyk},
title = {Synthesis 5-(pyrazolin-3-ylmethylidene)-2-thiohydantoins and 2-alkylsulfanyl-5-(pyrazolin-3-ylmethylidene)-3,5-dihydro-4H-imidazol-4-ones},
journal = {Russian Chemical Bulletin},
year = {2017},
volume = {66},
publisher = {Springer Nature},
month = {mar},
url = {http://link.springer.com/10.1007/s11172-017-1764-1},
number = {3},
pages = {506--510},
doi = {10.1007/s11172-017-1764-1}
}
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MLA
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Vorozhtsov, N. I., et al. āSynthesis 5-(pyrazolin-3-ylmethylidene)-2-thiohydantoins and 2-alkylsulfanyl-5-(pyrazolin-3-ylmethylidene)-3,5-dihydro-4H-imidazol-4-ones.ā Russian Chemical Bulletin, vol. 66, no. 3, Mar. 2017, pp. 506-510. http://link.springer.com/10.1007/s11172-017-1764-1.