Synthesis and Aminomethylation of 6-Amino-2-(dicyanomethylene)-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile Morpholinium Salt
A O Kurskova
1
,
Viktor V Dotsenko
2, 3
,
Konstantin A. Frolov
1
,
Inna V. Aksenova
3
,
Bogdan S. Krivokolysko
4
,
1
Laboratory “ChemEx”, V. Dal Lugansk State University, Lugansk, Ukraine
|
Publication type: Journal Article
Publication date: 2021-08-01
scimago Q4
wos Q4
SJR: 0.179
CiteScore: 1.4
Impact factor: 0.8
ISSN: 10703632, 16083350
General Chemistry
Abstract
Condensation of benzaldehyde with malononitrile and malononitrile dimer (2-aminopropene-1,1,3-tricarbonitrile) in the presence of an excess of morpholine in ethanol afforded the morpholinium salt of 6-amino-2-(dicyanomethylene)-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile. The latter, under the Mannich reaction conditions with the participation of primary amines and formaldehyde, gives 6-amino-2-(dicyanomethylene)-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile, 2-(dicyanomethylene)-6-(hydroxymethylamino)-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile or zwitterionic aminomethylation products, 6-(ammoniomethylamino)-3,5-dicyano-4-phenylpyridin-2-yl)dicyanomethanides. Structure of the obtained compounds was established using 2D NMR spectroscopy and single crystal X-ray diffraction analysis. In silico predictive analysis of the biological activity of new compounds was carried out.
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Kurskova A. O. et al. Synthesis and Aminomethylation of 6-Amino-2-(dicyanomethylene)-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile Morpholinium Salt // Russian Journal of General Chemistry. 2021. Vol. 91. No. 8. pp. 1471-1483.
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Kurskova A. O., Dotsenko V. V., Frolov K. A., Aksenov N. A., Aksenova I. V., Krivokolysko B. S., Krivokolysko S. G. Synthesis and Aminomethylation of 6-Amino-2-(dicyanomethylene)-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile Morpholinium Salt // Russian Journal of General Chemistry. 2021. Vol. 91. No. 8. pp. 1471-1483.
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RIS
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TY - JOUR
DO - 10.1134/s1070363221080089
UR - https://doi.org/10.1134/s1070363221080089
TI - Synthesis and Aminomethylation of 6-Amino-2-(dicyanomethylene)-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile Morpholinium Salt
T2 - Russian Journal of General Chemistry
AU - Kurskova, A O
AU - Dotsenko, Viktor V
AU - Frolov, Konstantin A.
AU - Aksenov, Nicolai A.
AU - Aksenova, Inna V.
AU - Krivokolysko, Bogdan S.
AU - Krivokolysko, Sergey G.
PY - 2021
DA - 2021/08/01
PB - Pleiades Publishing
SP - 1471-1483
IS - 8
VL - 91
SN - 1070-3632
SN - 1608-3350
ER -
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@article{2021_Kurskova,
author = {A O Kurskova and Viktor V Dotsenko and Konstantin A. Frolov and Nicolai A. Aksenov and Inna V. Aksenova and Bogdan S. Krivokolysko and Sergey G. Krivokolysko},
title = {Synthesis and Aminomethylation of 6-Amino-2-(dicyanomethylene)-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile Morpholinium Salt},
journal = {Russian Journal of General Chemistry},
year = {2021},
volume = {91},
publisher = {Pleiades Publishing},
month = {aug},
url = {https://doi.org/10.1134/s1070363221080089},
number = {8},
pages = {1471--1483},
doi = {10.1134/s1070363221080089}
}
Cite this
MLA
Copy
Kurskova, A. O., et al. “Synthesis and Aminomethylation of 6-Amino-2-(dicyanomethylene)-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile Morpholinium Salt.” Russian Journal of General Chemistry, vol. 91, no. 8, Aug. 2021, pp. 1471-1483. https://doi.org/10.1134/s1070363221080089.