volume 49 issue 9 pages 1301-1307

Reaction of Cyanoselenoacetamide with 1,3-Dicarbonyl Compound Anilinomethylene Derivatives

K A Frolov 1
V V Dotsenko 1
S G Krivokolysko 1
1
 
“ChemEx” Laboratory, Vladimir Dal’ East Ukrainian National University, Luhansk, Ukraine
Publication typeJournal Article
Publication date2013-11-22
scimago Q4
wos Q4
SJR0.243
CiteScore2.7
Impact factor1.0
ISSN00093122, 15738353
Organic Chemistry
Abstract
The reaction of cyanoselenoacetamide with a 2-anilinomethylene derivative of Meldrum’s acid (2 equiv. KOH, EtOH, 20°C) gives the 5-cyano-6-hydroseleno-2-oxo-1,2-dihydropyridine-3-carboxylic acid dipotassium salt. The latter reacts with alkyl halides to yield 5-cyano-6-(R-methylseleno)-2-oxo-1,2-dihydropyridine-3-carboxylic acids. Treatment of cyanoselenoacetamide with 2-anilinomethyl derivatives of dimedone and 1,3-cyclohexanedione is accompanied by oxidation and gives 2,2'-di-selane-1,2-diylbis(5-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitriles). The obtained diselanes undergo cleavage using alkyl halides in KOH to give 2-(R-methylseleno)-5-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitriles or selenopheno[2,3-b]quinolines as Thorpe–Ziegler cyclization products of the latter in low yields.
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GOST Copy
Frolov K. A., Dotsenko V. V., Krivokolysko S. G. Reaction of Cyanoselenoacetamide with 1,3-Dicarbonyl Compound Anilinomethylene Derivatives // Chemistry of Heterocyclic Compounds. 2013. Vol. 49. No. 9. pp. 1301-1307.
GOST all authors (up to 50) Copy
Frolov K. A., Dotsenko V. V., Krivokolysko S. G. Reaction of Cyanoselenoacetamide with 1,3-Dicarbonyl Compound Anilinomethylene Derivatives // Chemistry of Heterocyclic Compounds. 2013. Vol. 49. No. 9. pp. 1301-1307.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1007/s10593-013-1379-x
UR - https://doi.org/10.1007/s10593-013-1379-x
TI - Reaction of Cyanoselenoacetamide with 1,3-Dicarbonyl Compound Anilinomethylene Derivatives
T2 - Chemistry of Heterocyclic Compounds
AU - Frolov, K A
AU - Dotsenko, V V
AU - Krivokolysko, S G
PY - 2013
DA - 2013/11/22
PB - Springer Nature
SP - 1301-1307
IS - 9
VL - 49
SN - 0009-3122
SN - 1573-8353
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2013_Frolov,
author = {K A Frolov and V V Dotsenko and S G Krivokolysko},
title = {Reaction of Cyanoselenoacetamide with 1,3-Dicarbonyl Compound Anilinomethylene Derivatives},
journal = {Chemistry of Heterocyclic Compounds},
year = {2013},
volume = {49},
publisher = {Springer Nature},
month = {nov},
url = {https://doi.org/10.1007/s10593-013-1379-x},
number = {9},
pages = {1301--1307},
doi = {10.1007/s10593-013-1379-x}
}
MLA
Cite this
MLA Copy
Frolov, K. A., et al. “Reaction of Cyanoselenoacetamide with 1,3-Dicarbonyl Compound Anilinomethylene Derivatives.” Chemistry of Heterocyclic Compounds, vol. 49, no. 9, Nov. 2013, pp. 1301-1307. https://doi.org/10.1007/s10593-013-1379-x.