A new synthesis of 4-oxo-4,5-dihydro-1,3-oxazolium perchlorates from D-pantoamide

¹ Kuban State University, 149 Stavropolskaya Str., Krasnodar 350040, Russian Federation
² All-Russian Research Institute of Biological Plant Protection, Laboratory of plant growth regulators, 350039 Krasnodar, Russian Federation
³ Federal State Unitary Enterprise «Research Institute of Chemical Reactants and Ultrapure Compounds (IREA)», 3 Bogorodsky Shaft, Moscow 107076, Russia
⁴ ChemEx Lab, Vladimir Dal’ Lugansk National University, Lugansk, 91034 Russia.
⁵ North-Caucasus Federal University, 1 Pushkina St., 355009 Stavropol, Russian Federation
⁶ 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-a062

Abstract:

The reaction of D-(–)-pantolactone with ammonia leads to the formation of D-pantoamide, which reacts with Ас₂О and HClO₄ to give 5-[2-(acetoxy)-1,1-dimethylethyl]-2-methyl-4-oxo-4,5-dihydro-1,3-oxazolium perchlorate. The obtained 2-methyl-1,3-oxazolium perchlorate readily reacts with aromatic aldehydes to afford 2-(2-arylvinyl)-1,3-oxazolium perchlorates. The plant protecting properties of the obtained compounds were studied. We found that 2-(2-arylvinyl)-4-oxo-4,5-dihydro-1,3-oxazolium perchlorates are effective as antidotes towards herbicide 2,4-D but have no plant growth activity.

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