Synthesis of amido- and sulfamide of 1,3,4-thiadiazine

In order to reveal the difference between S, N-substituted 6-membered heterocyclic compounds, a series of amido and sulfamide 5,6,6-trimethyl-6 H-1,3,4-thiadiazine have been synthesized. The reaction of 2-(3-hydroxy-3-methylbutane-2-ylidene)hydrazine-1-carbothiamine with acetic anhydride has been carried out. At synthesis of N- (2- (3-hydroxy-3-methylbutane-2-ylidene) hydrazine-1-carbon thiol) aceto amide in the presence of trifluoroacetic acid, the N- (5,6,6-trimethyl-6 H-1,3,4-thiadiazine-2-yne)acetamide has been obtained. At synthesis of N-(5,6,6-trimethyl-6 H-1,3,4-thiadiazine-2-yne)acetamide by the reaction of 5,6,6-trimethyl-6 H-1,3,4-thiadiazine-2-amine with N- (5,6,6-trimethyl-6 H-1,3,4-thiadiazine-2-yne)acetamide has been carried out with acetic acid halide. 4-methyl-N-(5,6,6-trimethyl-6 H-1,3,4-thiadiazine-2-yne)-benzyl sulfamide has been synthesized by the interaction of 5,6,6-trimethyl-6 H-1,3,4- thiadiazine-2-amine with toluenesulfochloride. The correlation of ability of synthesized substances with the data of quantum chemical calculations of synthesized structures has been carried out. The conclusion has been made about the energy, the most stable configuration of intermediate and final products. Product structures have been defined by means of IR and NMR spectra along with elemental analyzes. The reaction mechanism has been discussed. (author)