| Synthesis of novel chiral fluorinating agents, （＋）- and （-）-N-fluoro-3-methyl-3-（4-methylphenyl）-2H-benzo[e] [ 1,2]thiazine- 1,1,4-triones |
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| 作者姓名： | Hui Min Sun ;Zhao Peng Liu ;Long Qian Tang |
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| 作者单位： | a National Institute for the Control of Pharmaceutical and Biological Products, Beijing 100050, China;b Department of Organic Chemistry, School of Pharmaceutical Sciences, Shandong University, Jinan 250012, China |
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| 基金项目： | Acknowledgment
This work was supported by the Scientific Research Foundation for the Returned Oversea Chinese Scholars of Shandong University. |
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| 摘 要： | Treatment of N-t-butylbenzenesulfonamide with an excess of BuLi, followed by the reaction with methyl 2-（4-methylphenyl）propanoate, gave the corresponding 2-carboxybenzenesulfonamide, which underwent a sequence of consecutive N-deprotective cyclization process mediated by TMSCI-NaI-MeCN reagent to afford the N-sulfonylimine. Following the bromination and ring expansion, 3-methyl-3-（4-methylphenyl）-2H-benzoe]1,2]thiazine-l,l,4-trione was obtained. Optical resolution of the racemic benzosultam using （-）-menthoxyacetyl chloride, furnished the optically p.ure （＋）- and （-）-3-methyl-3-（4-methylphenyl）-2H- benzoe]1,2]thiazine-1,1,4-triones, which were fluorinated with FC103 to produce the corresponding chiral N-F agents.
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| 关 键 词： | 环合作用 亲电子作用 化学 手性作用 |
Synthesis of novel chiral fluorinating agents, (+)- and (-)-N-fluoro-3-methyl-3-(4-methylphenyl)-2H-benzo [e] [1,2] thiazine-1,1,4-triones |
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| Hui Min Sun,;Zhao Peng Liu,;Long Qian Tang.Synthesis of novel chiral fluorinating agents, (+)- and (-)-N-fluoro-3-methyl-3-(4-methylphenyl)-2H-benzo [e] [1,2] thiazine-1,1,4-triones[J].Chinese Chemical Letters,2008,19(8):907-910. |
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| Authors: | Hui Min Sun Zhao Peng Liu Long Qian Tang |
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| Institution: | a National Institute for the Control of Pharmaceutical and Biological Products, Beijing 100050, China;b Department of Organic Chemistry, School of Pharmaceutical Sciences, Shandong University, Jinan 250012, China |
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| Abstract: | Treatment of N-t-butylbenzenesulfonamide with an excess of BuLi, followed by the reaction with methyl 2-(4-methylphenyl)propanoate, gave the corresponding 2-carboxybenzenesulfonamide, which underwent a sequence of consecutive N-deprotective cyclization process mediated by TMSCl-NaI-MeCN reagent to afford the N-sulfonylimine. Following the bromination and ring expansion, 3-methyl-3-(4-methylphenyl)-2H-benzoe]1,2]thiazine-1,1,4-trione was obtained. Optical resolution of the racemic benzosultam using (-)-menthoxyacetyl chloride, furnished the optically pure ( )- and (-)-3-methyl-3-(4-methylphenyl)-2H-benzoe]1,2]thiazine-1,1,4-triones, which were fluorinated with FClO3 to produce the corresponding chiral N-F agents. |
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| Keywords: | Benzosultams Cyclization TMSCl/NaI/MeCN Enantioselective electrophilic fluorinating agent Chirality |
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