ТНЕ NEW WAYS OF SYNTHESIS OF BIOLOGICALLY ACTIVE SULFONYLAZOTE-CONTAINING COMPOUNDS
The reactions of a number of 2,6-disubstituted 1,4,3,5-oxathiadiazine-4,4-dioxides with nucleophilic active reagents - water and amines (piperidine, morpholine) were studied. Simple and effective methods have been found for the preparation of N, N’-disubstituted sulfonylureas as a result of hydrolysis of the starting substrates and N, N-dialkyl-N’-(N’’,N’’-dialkylamidinosulfonyl) ureas in reactions with amines. The hydrolysis was carried out in water, catalyzed by bases (sodium carbonate, sodium hydroxide), and with an increase in the electron-deficient properties of one substituents of the 1,4,3,5-oxathiadiazine-4,4-dioxides are much easier to hydrolyze. A similar regularities is demonstrated by the reaction with amines. Due to the higher nucleophilicity of amines compared to water, the interaction with amines is much more active, and for 1,4,3,5-oxathiadiazine cycles with a strong electron- acceptoring substituent, the reaction should be carried out under moderate cooling. To suppress the competing hydrolysis reaction, all reactions with amines were carried out in a flow of dried argon. Taking into account the influence of the electronic properties of the substituent in the initial heterocycle, the optimal conditions for carrying out the described transformations have been experimentally revealed. The reactions proceed with high selectivity, the products are isolated in yields close to quantitative. Tests of samples of synthesized N,N’-disubstituted sulfonylureas and N,N-dialkyl-N’-(N’’,N’’-dialkylamidinosulfonyl) ureas showed their high bactericidal activity. Also, the substituted amidinosulfonylurea sample has significant fungicidal activity. The structure of the reaction products was proved by IR spectroscopy, elemental analysis data.