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An alternative route for synthesis of chiral 4-substituted 1-arenesulfonyl-2-imidazolidinones: Unusual utility of (4 S,5 S)- and (4 R,5 R)-4,5-dimethoxy-2-imidazolidinones and x-ray crystallography
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نویسنده
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al-swaidan i.a. ,alanazi a.m. ,el-azab a.s. ,abdel-aziz a.a.-m.
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منبع
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journal of chemistry - 2013 - دوره : 2013 - شماره : 0
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چکیده
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An unusual synthesis of (s)-1-arenesulfonyl-4-(1-adamantyl)-2- imidazolidinones 15a-d and (r)-1-arenesulfonyl-4-tert-butyl-2-imidazolidinones 19a-d has been developed from trans-1-apocamphanecarbonyl-4,5-dimethoxy-2- imidazolidinones 6 and 7 as chiral synthons. diastereomerically pure trans-1-apocamphanecarbonyl-4,5-dimethoxy-2-imidazolidinones 6 and 7 were successfully subjected to regioselective reduction using bulky organocuprates that afforded 1-apocamphanecarbonyl-5-methoxy-2-imidazolidinones 10 and 11. this new finding was used for synthesis of chiral 4-substituted 2-imidazolidinones 15a-d and 19a-d through the corresponding intermediates 13 and 17 by treatment with steric bulky tert-butylcuprate or 1-adamantylcuprate. © 2013 ibrahim a. al-swaidan et al.
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آدرس
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department of pharmaceutical chemistry,college of pharmacy,king saud university,p.o. box 2457, Saudi Arabia, department of pharmaceutical chemistry,college of pharmacy,king saud university,p.o. box 2457, Saudi Arabia, department of pharmaceutical chemistry,college of pharmacy,king saud university,p.o. box 2457,riyadh 11451,saudi arabia,department of organic chemistry,faculty of pharmacy,al-azhar university, Egypt, department of pharmaceutical chemistry,college of pharmacy,king saud university,p.o. box 2457,riyadh 11451,saudi arabia,department of medicinal chemistry,faculty of pharmacy,university of mansoura, Egypt
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Authors
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