Oxidation of thioamides with the DMSO–HCl system: a convenient and efficient method for the synthesis of 1,2,4-thiadiazoles, isothiazolo-[5,4-b]pyridines, and heterocyclic disulfides
Тип публикации: Journal Article
Дата публикации: 2013-07-10
scimago Q4
wos Q4
БС3
SJR: 0.243
CiteScore: 2.7
Impact factor: 1.0
ISSN: 00093122, 15738353
Organic Chemistry
Краткое описание
Brief heating of 3-aryl-2-cyanothioacrylamides in the DMSO–HCl system gave (2E,2′E)-2,2′-(1,2,4-thia-diazol-3,5-diyl)bis(3-arylacrylonitriles). Under the same conditions, cyclic thioamides (derivatives of 2-thioxo-1,2-dihydropyridine-3-carbonitrile and quinoxaline-2(1H)-thione) gave good yields of the bis(hetaryl) disulfides. Ethyl 4-(4-chlorophenyl)-5-cyano-2-phenyl-6-thioxo-1,4,5,6-tetra-hydropyridine-3-carboxylate gave a mixture of oxidation products at the sulfur atom and the hetero-cycle when treated with the DMSO–HCl system. Oxidation of N-aryl-4,6-dimethyl-2-thioxo-1,2-di-hydropyridine-3-carboxamides gave isothiazolo[5,4-b]pyridines.
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Dotsenko V. V., Krivokolysko S. G. Oxidation of thioamides with the DMSO–HCl system: a convenient and efficient method for the synthesis of 1,2,4-thiadiazoles, isothiazolo-[5,4-b]pyridines, and heterocyclic disulfides // Chemistry of Heterocyclic Compounds. 2013. Vol. 49. No. 4. pp. 636-644.
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Dotsenko V. V., Krivokolysko S. G. Oxidation of thioamides with the DMSO–HCl system: a convenient and efficient method for the synthesis of 1,2,4-thiadiazoles, isothiazolo-[5,4-b]pyridines, and heterocyclic disulfides // Chemistry of Heterocyclic Compounds. 2013. Vol. 49. No. 4. pp. 636-644.
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TY - JOUR
DO - 10.1007/s10593-013-1291-4
UR - https://doi.org/10.1007/s10593-013-1291-4
TI - Oxidation of thioamides with the DMSO–HCl system: a convenient and efficient method for the synthesis of 1,2,4-thiadiazoles, isothiazolo-[5,4-b]pyridines, and heterocyclic disulfides
T2 - Chemistry of Heterocyclic Compounds
AU - Dotsenko, V V
AU - Krivokolysko, S G
PY - 2013
DA - 2013/07/10
PB - Springer Nature
SP - 636-644
IS - 4
VL - 49
SN - 0009-3122
SN - 1573-8353
ER -
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@article{2013_Dotsenko,
author = {V V Dotsenko and S G Krivokolysko},
title = {Oxidation of thioamides with the DMSO–HCl system: a convenient and efficient method for the synthesis of 1,2,4-thiadiazoles, isothiazolo-[5,4-b]pyridines, and heterocyclic disulfides},
journal = {Chemistry of Heterocyclic Compounds},
year = {2013},
volume = {49},
publisher = {Springer Nature},
month = {jul},
url = {https://doi.org/10.1007/s10593-013-1291-4},
number = {4},
pages = {636--644},
doi = {10.1007/s10593-013-1291-4}
}
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Dotsenko, V. V., and S G Krivokolysko. “Oxidation of thioamides with the DMSO–HCl system: a convenient and efficient method for the synthesis of 1,2,4-thiadiazoles, isothiazolo-[5,4-b]pyridines, and heterocyclic disulfides.” Chemistry of Heterocyclic Compounds, vol. 49, no. 4, Jul. 2013, pp. 636-644. https://doi.org/10.1007/s10593-013-1291-4.
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