- Synthesis and ring opening reactions of tetrahydroimidazo-[1,5-b][1,2,4]oxadiazol-2(1H)-thiones
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1,3-Dipolar cycloaddition of imidazoline 3-oxides 1 with methylisothiocyanate proceeds regio- and diastereoselectively to give tetrahydroimidazo[1,5-b][1,2,4]oxadiazol-2(1H)-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 50°C 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.
- Coskun, Necdet,Tirli Tat, Fatma
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