NEW METHOD OF SYNTHESIS OF 4H-1,3,5-OXADIAZINE DERIVATIVES
Kyrychenko K.O., Zadorozhnii P.V., Kiselev V.V., Kharchenko A.V.
SHEE «Ukrainian State University of Chemical Technology»,
A series of N-amidoalkilated thioureas 4 have been obtained on the base of 4-chloro-N-(2,2,2-trichloro-1-hydroxyethyl)benzamide 1 via the intermediate stage of the isothiocyanate 2 formation. The compounds 4 are perspective and polyfunctional reagents. They have been used successfully by us as synthons in the new 4H-1,3,5-oxadiazine derivatives’ synthesis. Degidrosulfurization of thioureas 4 have been conducted at reflux in anhydrous acetonitrile with 10%-excess of dicyclohexylcarbodiimide (DCC) for 50-60 min.
Compound 5 has been prepared in acceptable yields and without special difficulties isolated from the reaction mixture.
The synthesized structures of the compounds have been fully characterized by IR, 1H and 13C NMR spectroscopy and X-ray crystallographic analysis.