EventsThe 25th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-25-11739 (registering DOI)
This submission belongs to the session S1. General Organic Synthesis of the event The 25th International Electronic Conference on Synthetic Organic Chemistry
Published date
14 Nov, 2021
Academic Editor
author-avatarJulio A. Seijas
Citation
Ann Kurskova, Krivokolysko Sergey, Frolov Konstantin, Dotsenko Victor, Synthesis and aminomethylation of 6-amino-2-(dicyanomethylene)-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile morpholinium salt, in Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry, 15 November–30 November 2021, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-25-11739
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Synthesis and aminomethylation of 6-amino-2-(dicyanomethylene)-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile morpholinium salt

Ann Kurskova 1
Krivokolysko Sergey 2
Frolov Konstantin 3
Dotsenko Victor 4
1. Laboratory “ChemEx,” V. Dal Lugansk State University, Lugansk, Ukraine
2. Dr. V. Dal Lugansk State University, Lugansk St. Luke Lugansk State Medical University, Lugansk
3. Laboratory “ChemEx,” V. Dal Lugansk State University, Lugansk St. Luke Lugansk State Medical University, Lugansk
4. Dr. Kuban State University, Krasnodar North Caucasus Federal University, Stavropol
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

Keywords
malononitrile dimer
2-(dicyanomethylene)-1,2-dihydropyridines
aminomethylation
Mannich reaction
Manuscript
sciforum_051608_original-done.pdf
Design, synthesis and structural characterization of a novel asymmetric hydrazone-thiosemicarbazone ligand with the aim of obtaining interesting metallosupramolecular architectures
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