Oxirane-2,2-dicarboxamides: synthesis, reactions and biological activity

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

Published: 08 November 2016 by MDPI in The 20th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-20-a063

Abstract:

The mild Radziszewski oxidation of 3-aryl-2-cyanoacrylamides with H₂O₂–NaOH (or H₂O₂–Na₂CO₃) 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

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