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

Abstract

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.