Synthesis of 6-R-N-aryl-4-(trichloromethyl)-4H-1,3,5-oxadiazin-2-amines based on N-(2,2,2-trichloro-1-(3-R-thioureido)ethyl)carboxamides: Their spectral characteristics and molecular structure

In this work, we report the synthesis of a series of new 4H-1,3,5-oxadiazine derivatives. The method of their production is based on the dehydrosulfurization reaction of N-(2,2,2-trichloro-1-(3-R-thioureido)ethyl)carboxamides under the action of a mixture of iodine and triethylamine in DMF. A possible reaction mechanism has been proposed. The target products have been obtained in 58%–75% yield. The structure of the obtained compounds has been confirmed by ¹H, ¹³C NMR, IR spectroscopy data, and x-ray diffraction analysis carried out for 6-(tert-butyl)-N-phenyl-4-(trichloromethyl)-4H-1,3,5-oxadiazin-2-amine.