Novel [4 + 2] Cycloaddition Reaction of Aryl-Methylidenemalononitriles to Unsaturated Chalcogen Amides. Synthesis, Structure, and Properties of Triethylammonium 3,5,5-Tricyano-1,4,5,6-Tetrahydropyridine-2-Selenolates and -Thiolates
Тип публикации: Journal Article
Дата публикации: 2013-11-22
scimago Q4
wos Q4
БС3
SJR: 0.243
CiteScore: 2.7
Impact factor: 1.0
ISSN: 00093122, 15738353
Organic Chemistry
Краткое описание
Reaction of arylmethylidenemalononitriles with 3-aryl-2-cyanoprop-2-eneselenoamides in the presence of Et3N gave triethylammonium 4,6-diaryl-3,5,5-tricyano-1,4,5,6-tetrahydropyridine-2-selenolates. A similar reaction with cyclohexylidenecyanothioacetamide yields triethylammonium 4-aryl-1,5,5-tri-cyano-3-azaspiro[5.5]undec-1-ene-2-thiolate. Alkylation of the obtained selenolates and thiolates gives 6-(alkylseleno)-2,4-diaryl-1,4-dihydropyridine-3,3,5(2H)-tricarbonitriles and 4-(alkylthio)-2-aryl-3-aza- spiro[5.5]undec-4-ene-1,1,5-tricarbonitriles, respectivelly. The structure of 2,4-di(2-furyl)-6-{[2-(4-methylphenyl)-2-oxoethyl]seleno}-1,4-dihydropyridine-3,3,5(2H)-tricarbonitrile has been confirmed by the X-ray structural analysis.
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Frolov K. A. et al. Novel [4 + 2] Cycloaddition Reaction of Aryl-Methylidenemalononitriles to Unsaturated Chalcogen Amides. Synthesis, Structure, and Properties of Triethylammonium 3,5,5-Tricyano-1,4,5,6-Tetrahydropyridine-2-Selenolates and -Thiolates // Chemistry of Heterocyclic Compounds. 2013. Vol. 49. No. 9. pp. 1289-1300.
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Frolov K. A., Dotsenko V. V., Krivokolysko S. G., Kostyrko E. O. Novel [4 + 2] Cycloaddition Reaction of Aryl-Methylidenemalononitriles to Unsaturated Chalcogen Amides. Synthesis, Structure, and Properties of Triethylammonium 3,5,5-Tricyano-1,4,5,6-Tetrahydropyridine-2-Selenolates and -Thiolates // Chemistry of Heterocyclic Compounds. 2013. Vol. 49. No. 9. pp. 1289-1300.
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TY - JOUR
DO - 10.1007/s10593-013-1378-y
UR - https://doi.org/10.1007/s10593-013-1378-y
TI - Novel [4 + 2] Cycloaddition Reaction of Aryl-Methylidenemalononitriles to Unsaturated Chalcogen Amides. Synthesis, Structure, and Properties of Triethylammonium 3,5,5-Tricyano-1,4,5,6-Tetrahydropyridine-2-Selenolates and -Thiolates
T2 - Chemistry of Heterocyclic Compounds
AU - Frolov, K A
AU - Dotsenko, V V
AU - Krivokolysko, S G
AU - Kostyrko, E O
PY - 2013
DA - 2013/11/22
PB - Springer Nature
SP - 1289-1300
IS - 9
VL - 49
SN - 0009-3122
SN - 1573-8353
ER -
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@article{2013_Frolov,
author = {K A Frolov and V V Dotsenko and S G Krivokolysko and E O Kostyrko},
title = {Novel [4 + 2] Cycloaddition Reaction of Aryl-Methylidenemalononitriles to Unsaturated Chalcogen Amides. Synthesis, Structure, and Properties of Triethylammonium 3,5,5-Tricyano-1,4,5,6-Tetrahydropyridine-2-Selenolates and -Thiolates},
journal = {Chemistry of Heterocyclic Compounds},
year = {2013},
volume = {49},
publisher = {Springer Nature},
month = {nov},
url = {https://doi.org/10.1007/s10593-013-1378-y},
number = {9},
pages = {1289--1300},
doi = {10.1007/s10593-013-1378-y}
}
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Frolov, K. A., et al. “Novel [4 + 2] Cycloaddition Reaction of Aryl-Methylidenemalononitriles to Unsaturated Chalcogen Amides. Synthesis, Structure, and Properties of Triethylammonium 3,5,5-Tricyano-1,4,5,6-Tetrahydropyridine-2-Selenolates and -Thiolates.” Chemistry of Heterocyclic Compounds, vol. 49, no. 9, Nov. 2013, pp. 1289-1300. https://doi.org/10.1007/s10593-013-1378-y.
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