2022-03-302022-03-302003-04Coşkun, N. ve Tat, F. T. (2003). “Synthesis and ring opening reactions of tetrahydroimidazo-[1,5-b][1,2,4]oxadiazol-2(1H)-thiones”. Phosphorus Sulfur and Silicon and the Related Elements, 178(4), 881-886.1042-6507https://doi.org/10.1080/10426500307788https://www.tandfonline.com/doi/abs/10.1080/10426500307788http://hdl.handle.net/11452/254251,3-Dipolar cycloaddition of imidazoline 3-oxides 1 with methylisothiocyanate proceeds regio- and diastereoselectively to give tetrahydroimidazo[1,5-b][1,2,4]oxadiazol-2(1 H)-thiones 3 in high yields. The cis configuration of the adducts were proved by our double cis elimination test as well as by NOESY experiments The imidazooxadiazol-2-thiones 3a-e were treated with concentrated HCl in ethanol at 50degreesC to give the corresponding 4 H[1,2,4]oxadiazole-5-thione only in the cases where the substituent at C-6 is an aryl.eninfo:eu-repo/semantics/closedAccessChemistryImidazoline 3-oxides1,3-dipolar cycloadditionDiastereoselective additionAryl isocyanatesRegioArticle0001823787000252-s2.0-00388117458818861784Chemistry, inorganic and nuclearChemistry, organicNitrones; Direct; HydroxylaminesArticleCycloadditionNuclear Overhauser effectStereochemistryTemperatureAlcoholImidazoline 3 oxideImidazoline derivativeMethyl isocyanateTetrahydroimidazo[1,5 b][1,2,4]oxadiazol 2(1h) thioneThioketoneUnclassified drug