Synthesis and reactivity of tetrahydroimidazo [1,5-b][1,2,4]oxadiazol-2(1H)-thiones

被引：0
|
作者：
Coskun, N [1 ]
Tat, FT [1 ]
机构：
[1] Uludag Univ, Dept Chem, TR-16059 Bursa, Turkey
来源：
TURKISH JOURNAL OF CHEMISTRY | 2004年 / 28卷 / 01期
关键词：
imidazoline; 3-oxides; 1,3-dipolar cycloaddition; tetrahydroimidazo[1,5-b][1,2,4]oxadiazol-2(1H)-thiones; 4H-[1,2,4]oxadiazole-5-thione;
D O I：
暂无
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
1,3-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.
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页码：1 / 7
页数：7
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