Synthesis of isomeric 3-phenyl-5-(pyridylmethylene)-2-thiohydantoins and their S-methylated derivatives. Molecular and crystal structures of (5Z)-3-phenyl-5-(pyridin-2-ylmethylene)-2-thiohydantoin and (5Z)-2-methylthio-3- phenyl-5-(pyridin-2-ylmethylene)-3,5-dihydro-4H-imidazol-4-one
Publication type: Journal Article
Publication date: 2004-12-01
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
General Chemistry
Abstract
Three procedures were used for the synthesis of α-, β, and γ-pyridyl-substituted (5Z)-3-phenyl-5-(pyridylmethylene)-2-thiohydantoins: the reaction of 2-thiohydantoin with the corresponding aldehyde in AcOH in the presence of AcONa, the two-step one-pot synthesis with the use of the same starting compounds, and three-component condensation of aryl isothiocyanate, glycine, and aldehyde in AcOH. Alkylation of the resulting thiohydantoins with iodomethane in the presence of a base afforded the corresponding S-methylated derivatives, viz., 2-methylthio-3-phenyl-5-(pyridylmethylene)-3,5-dihydro-4H-imidazol-4-ones. The structures of (5Z)-3-phenyl-5-(pyridin-2-ylmethylene)-2-thioxoimidazolin-4-one and (5Z)-2-methylthio-3-phenyl-5-(pyridin-2-ylmethylene)-3,5-dihydro-4H-imidazol-4-one were established by X-ray diffraction analysis.
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Majouga A. G. et al. Synthesis of isomeric 3-phenyl-5-(pyridylmethylene)-2-thiohydantoins and their S-methylated derivatives. Molecular and crystal structures of (5Z)-3-phenyl-5-(pyridin-2-ylmethylene)-2-thiohydantoin and (5Z)-2-methylthio-3- phenyl-5-(pyridin-2-ylmethylene)-3,5-dihydro-4H-imidazol-4-one // Russian Chemical Bulletin. 2004. Vol. 53. No. 12. pp. 2850-2855.
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Majouga A. G., Beloglazkina E. K., Vatsadze S. Z., Frolova N., Zyk N. V. Synthesis of isomeric 3-phenyl-5-(pyridylmethylene)-2-thiohydantoins and their S-methylated derivatives. Molecular and crystal structures of (5Z)-3-phenyl-5-(pyridin-2-ylmethylene)-2-thiohydantoin and (5Z)-2-methylthio-3- phenyl-5-(pyridin-2-ylmethylene)-3,5-dihydro-4H-imidazol-4-one // Russian Chemical Bulletin. 2004. Vol. 53. No. 12. pp. 2850-2855.
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TY - JOUR
DO - 10.1007/s11172-005-0201-z
UR - http://link.springer.com/10.1007/s11172-005-0201-z
TI - Synthesis of isomeric 3-phenyl-5-(pyridylmethylene)-2-thiohydantoins and their S-methylated derivatives. Molecular and crystal structures of (5Z)-3-phenyl-5-(pyridin-2-ylmethylene)-2-thiohydantoin and (5Z)-2-methylthio-3- phenyl-5-(pyridin-2-ylmethylene)-3,5-dihydro-4H-imidazol-4-one
T2 - Russian Chemical Bulletin
AU - Majouga, A G
AU - Beloglazkina, E K
AU - Vatsadze, S. Z.
AU - Frolova, N.A.
AU - Zyk, N. V.
PY - 2004
DA - 2004/12/01
PB - Springer Nature
SP - 2850-2855
IS - 12
VL - 53
SN - 1066-5285
SN - 1573-9171
ER -
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@article{2004_Majouga,
author = {A G Majouga and E K Beloglazkina and S. Z. Vatsadze and N.A. Frolova and N. V. Zyk},
title = {Synthesis of isomeric 3-phenyl-5-(pyridylmethylene)-2-thiohydantoins and their S-methylated derivatives. Molecular and crystal structures of (5Z)-3-phenyl-5-(pyridin-2-ylmethylene)-2-thiohydantoin and (5Z)-2-methylthio-3- phenyl-5-(pyridin-2-ylmethylene)-3,5-dihydro-4H-imidazol-4-one},
journal = {Russian Chemical Bulletin},
year = {2004},
volume = {53},
publisher = {Springer Nature},
month = {dec},
url = {http://link.springer.com/10.1007/s11172-005-0201-z},
number = {12},
pages = {2850--2855},
doi = {10.1007/s11172-005-0201-z}
}
Cite this
MLA
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Majouga, A. G., et al. “Synthesis of isomeric 3-phenyl-5-(pyridylmethylene)-2-thiohydantoins and their S-methylated derivatives. Molecular and crystal structures of (5Z)-3-phenyl-5-(pyridin-2-ylmethylene)-2-thiohydantoin and (5Z)-2-methylthio-3- phenyl-5-(pyridin-2-ylmethylene)-3,5-dihydro-4H-imidazol-4-one.” Russian Chemical Bulletin, vol. 53, no. 12, Dec. 2004, pp. 2850-2855. http://link.springer.com/10.1007/s11172-005-0201-z.