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| 10-苄基吖啶酮的合成及其与硼氢化钠还原反应研究 | |
| 引用本文： | 高春梅,刘华臣,蒋宇扬,谭春燕,曹德榕.10-苄基吖啶酮的合成及其与硼氢化钠还原反应研究[J].有机化学,2008,28(10):1803-1806. |
| 作者姓名： | 高春梅 刘华臣 蒋宇扬 谭春燕 曹德榕 |
| 作者单位： | 1. 广东省化学生物学重点实验室清华大学深圳研究生院,深圳,518055 2. 华南理工大学化学科学学院,广州,510640 |
| 基金项目： | 国家自然科学基金，中国博士后科研项目 |
| 摘 要： | 合成了一系列的10-苄基吖啶酮类化合物, 并探讨了一种用硼氢化钠氢化还原吖啶酮制备10-苄基-9,10-二氢吖啶的简便方法. 吖啶酮1与氯化苄及其衍生物2在氢化钠/N,N-二甲基甲酰胺/碘化钾中反应高产率生成10-苄基吖啶酮类化合物3; 3经硼氢化钠氢化还原生成10-苄基-9,10-二氢吖啶类化合物4, 产率88%～96%. 反应中没有得到预期的产物10-苄基-9,10-二氢吖啶醇类化合物4’, 其反应机理可能是3首先被硼氢化钠还原成醇中间体4’, 4’在硼氢化钠存在下不稳定, 迅速地被进一步还原成4. |
| 关 键 词： | 9 10-二氢吖啶 吖啶酮 硼氢化钠 吖啶 |
| 收稿时间： | 2008-1-21 |
| 修稿时间： | 2008-3-19 |
Synthesis of 10-Benzyl-9-acridone and Its Reduction with NaBH4 |
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| GAO,Chun-Mei,LIU,Hua-Chen,JIANG,Yu-Yang,TAN,Chun-Yan,CAO,De-Rong.Synthesis of 10-Benzyl-9-acridone and Its Reduction with NaBH4[J].Chinese Journal of Organic Chemistry,2008,28(10):1803-1806. | |
| Authors: | GAO Chun-Mei LIU Hua-Chen JIANG Yu-Yang TAN Chun-Yan CAO De-Rong |
| Institution: | (a Key Laboratory of Chemical Biology of Guangdong Province, the Graduate School at Shenzhen, Tsinghua University, Shenzhen 518055) (b College of Chemistry, South China University of Technology, Guangzhou 510640) |
| Abstract: | A series of 10-benzyl-9-acridones were synthesized and their reduction with NaBH4 to 10-benzy1-9,10-dihydroacridine derivatives was developed. Acridone 1 reacted with benzyl chlorides 2 in NaH/DMF/KI to give 10-benzyl-9-acridones 3 in high yields. Subsequent reduction of 3 with NaBH4 gave 10-benzy1-9,10-dihydroacridine derivatives 4 with yields of 88%～96%. However, the expected 10-benzy1-9,10-dihydro-9-hydroxyacridine derivatives 4’ were not detected. Probably, 4’ is the first reduc-tion product, which is not stable and reduced to 4 by NaBH4 immediately. |
| Keywords: | 9 10-dihydroacridine acridone NaBH4 acridine |
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