1-alkyl 3,5-diallyl isocyanurates as synthetic building blocks for sulfur-containing macroheterocycles

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2-Sulfanylethanol was added to readily available 1-alkyl 3,5-diallyl isocyanurates to obtain 1-alkyl 3,5-bis[3-(2-hydroxyethylsulfanyl)propyl] isocyanurates. Treatment of the products with thionyl chloride gave 1-alkyl 3,5-bis[3-(2-chloroethylsulfanyl)propyl] isocyanurates whose reaction with thiourea followed by hydrolysis resulted in preparation 1-alkyl 3,5-bis[3-(2-sulfanylethylsulfanyl)propyl] isocyanurates. Oxiative cyclization of the latter gave macrocyclic disulfides in 56–75% yields. The composition and structure of the macrocyclic disulfides were established on the basis of the elemental and X-ray diffraction analyses, 1H and 13C NMR and IR spectra, as well as MALDI-TOF and electron impact mass spectra.