Synthesis and Aminomethylation of 2-Amino-4-(2-chlorophenyl)-6-(dicyanomethyl)-1,4-dihydropyridine-3,5-dicarbonitrile N-Methylmorpholinium Salt

A O Kurskova; V V Dotsenko; K A Frolov; N A Aksenov; I V Aksenova; B S Krivokolysko; A A Peresypkina; E A Chigorina; S G Krivokolysko

doi:10.1134/S1070363222050061

Synthesis and Aminomethylation of 2-Amino-4-(2-chlorophenyl)-6-(dicyanomethyl)-1,4-dihydropyridine-3,5-dicarbonitrile N-Methylmorpholinium Salt

Russ J Gen Chem. 2022;92(5):779-790. doi: 10.1134/S1070363222050061. Epub 2022 Jun 14.

Authors

A O Kurskova¹, V V Dotsenko^{2

3}, K A Frolov¹, N A Aksenov³, I V Aksenova³, B S Krivokolysko⁴, A A Peresypkina⁵, E A Chigorina^{6

7}, S G Krivokolysko^{1

4}

Affiliations

¹ ChemEx Laboratory, V. Dahl Lugansk State University, 91034 Lugansk, Ukraine.
² Kuban State University, 350040 Krasnodar, Russia.
³ North Caucasian Federal University, 355009 Stavropol, Russia.
⁴ Lugansk State Medical University named after St. Luke, 91045 Lugansk, Ukraine.
⁵ Belgorod State National Research University, 308015 Belgorod, Russia.
⁶ National Research Center "Kurchatov Institute" - IREA, 107076 Moscow, Russia.
⁷ National Research Center "Kurchatov Institute", 123182 Moscow, Russia.

Abstract

Sequential reaction of 2-chlorobenzaldehyde, cyanothioacetamide, and malononitrile dimer in the presence of an excess of N-methylmorpholine resulted in the formation of N-methylmorphlinium salt of 2-amino-4-(2-chlorophenyl)-6-(dicyanomethyl)-1,4-dihydropyridine-3,5-dicarbonitrile. The resulting salt reacts under Mannich conditions with primary amines and an excess of formaldehyde to form substituted 2-alkylamino-4-(dicyanomethylene)-3,7-diazabicyclo[3.3.1]non-2-ene-1,5-dicarbonitriles. Structure of the key compound was confirmed by single crystal X-ray diffraction analysis.

Keywords: 1,4-dihydropyridines; 2-aminopropene-1,1,3-tricarbonitrile; aminomethylation; calculated biological activity; cyanothioacetamide.