2022-05-132022-05-132004Coşkun, N. ve Tat, F. T. (2004). “Synthesis and reactivity of tetrahydroimidazo [1,5-b][1,2,4]oxadiazol-2(1H)-thiones”. Turkish Journal of Chemistry, 28(1), 1-7.1300-0527https://dctubitak.researchcommons.org/chem/vol28/iss1/1/http://hdl.handle.net/11452/264441,3-Dipolar cycloaddition of imidazoline 3-oxides I with methylisothiocyanate proceeds regio- and diastereoselectively to give tetrahydroimidazo[1,5-b][1,2,4]oxadiazol-2(1H)-thiones 3 in high yields. The cis configuration of the adducts was proved by our double cis elimination test as well as by NOESY experiments. Adducts 3a-c undergo ring opening at reflux in acetonitrile to give imidazoles while 3d-e undergo retro dipolar cycloaddition to give the starting nitrones 1d-e. The imidazooxadiazol-2-thiones 3a-e were treated with concentrated HCl in ethanol at 50degreesC to give the corresponding 4H-[1,2,4]oxadiazole-5-thione only in cases in which the substituent at C-6 is an aryl.eninfo:eu-repo/semantics/openAccessChemistryEngineeringImidazoline 3-oxides1,3-dipolar cycloadditionTetrahydroimidazo[1,5-b][1,2,4]oxadiazol-2(1H)-thiones4H-[1,2,4]oxadiazole-5-thione1,3-dipolar cycloadditionImidazoline 3-oxidesDiastereoselective additionRegioNitronesArticle0002206801000012-s2.0-184268986217281Chemistry, multidisciplinaryEngineering, chemicalNitrones; Direct; HydroxylaminesArticleCycloadditionHigh temperatureNuclear overhauser effectQuantum yieldRing openingStereochemistryCyanic acid derivativeHydrochloric acidImidazoline derivativeMethylisothiocyanateOxadiazole derivativeUnclassified drug