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.
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Oxirane-2,2-dicarboxamides: synthesis, reactions and biological activity
Published: 08 November 2016 by MDPI in The 20th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
Keywords: Radziszewski oxidation, oxiranes, aminolysis, beta-amino alcohols, tartronamide, biological activity