EventsThe 20th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-20-a063
This submission belongs to the session a. General Organic Synthesis of the event The 20th International Electronic Conference on Synthetic Organic Chemistry
Published date
08 Nov, 2016
Citation
Victor V. Dotsenko, Yulia E. Aniskina, Vladimir D. Strelkov, Lyudmila V. Dyadyuchenko, Gennady D. Krapivin, Oxirane-2,2-dicarboxamides: synthesis, reactions and biological activity, in Proceedings of The 20th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2016, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-20-a063
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Oxirane-2,2-dicarboxamides: synthesis, reactions and biological activity

Victor V. Dotsenko 1,2,3
Yulia E. Aniskina 1
Vladimir D. Strelkov 1,4
Lyudmila V. Dyadyuchenko 4
Gennady D. Krapivin 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
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
Manuscript
ECSOC 20 abstract 5 oxiranes.pdf
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