SYNTHESIS OF 3-(1-ARYLAMINOCARBONYL-5-AMINO)-1,2,4-TRIAZOLYL BENZYL SULFIDE, SULFOXIDE AND SULFONE

3-(1-arylaminocarbonyl-5-amino)-1,2,4-triazolyl benzyl sulfides were s ynthesized by the reaction of 5-amino-3-benzylthio-1,2,4-triazole and its analogue with the aryl isocyanate. It was found that there was gre at influence by the property and position of substituents X, Y on the chemical shift of H-N-2 in the H-1 NMR spectra. By means of molecular mechanics calculations, the substituent effect on the chemical shift o f H-N-2 was rationalized. The chemocontrolled oxidation of 3-(1-arylam inocarbonyl-5-amino)-1,2,4-triazolyl benzyl sulfide to sulfoxide and s ulfone respectively was performed after a careful study of the influen ce of the concentration of H2O2 and the reaction temperature on the ox idation reaction. In H-1 NMR spectra of sulfoxides(II), the protons of a methylene group near the SO chiral center coupled to appear as a qu artet in the AB pattern. The SO, SO2 decreased the electronic density around H-N-2, 5-NH2, and thus moved the proton absorption to a lower h eld. The experimental showed that the ratio of sulfoxide(II)/sulfone(I II) was influenced by the electronic property of substituents X, Y on the aryl moiety.