Please login first
Oxirane-2,2-dicarboxamides: synthesis, reactions and biological activity
* 1, 2, 3 , 1 , 1, 4 , 4 , 5
1  Kuban State University, 149 Stavropolskaya Str., Krasnodar 350040, Russian Federation
2  ChemEx Lab, Vladimir Dal’ Lugansk National University, Lugansk, 91034 Russia.
3  North-Caucasus Federal University, 1 Pushkina St., 355009 Stavropol, Russian Federation
4  All-Russian Research Institute of Biological Plant Protection, Laboratory of plant growth regulators, 350039 Krasnodar, Russian Federation
5  Kuban State Technological University, 2 Moskovskaya st., 350072 Krasnodar, Russian Federation


The mild Radziszewski oxidation of  3-aryl-2-cyanoacrylamides with H2O2–NaOH (or H2O2Na2CO3) system leads to the formation of oxirane-2,2-dicarboxamides in good yields. The reactions and structure of the obtained products were studied. The aminolysis of the oxirane-2,2-dicarboxamides effected by primary amines occurs in keeping with Krasusky rule to afford 2-(1-R-amino-ethyl)-3-aryl-2-hydroxymalonamides or tartronamide.We found that 3-(4-methoxyphenyl)oxirane-2,2-dicarboxamide exhibited moderate activity both as plant growth regulator and 2,4-D antidote.

Keywords: Radziszewski oxidation, oxiranes, aminolysis, beta-amino alcohols, tartronamide, biological activity