| 6-溴-N-芳基噻吩[2,3-d]并嘧啶-4-胺类化合物的合成新方法 |
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| 引用本文： | 詹冬梅,李思远,赵红莉,蓝闽波.6-溴-N-芳基噻吩[2,3-d]并嘧啶-4-胺类化合物的合成新方法[J].有机化学,2011,31(2). |
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| 作者姓名： | 詹冬梅 李思远 赵红莉 蓝闽波 |
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| 作者单位： | 1. 上海市功能性材料化学重点实验室,华东理工大学分析测试中心,上海,200237
2. 上海市功能性材料化学重点实验室,华东理工大学分析测试中心,上海,200237;华东理工大学生物反应器工程国家重点实验室,上海,200237 |
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| 基金项目： | 上海市科委(No.10dz2220500)资助项目 |
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| 摘 要： | 研究了6-溴-N-3-氯-4-(3-氟苄氧基)苯基]噻吩2,3-d]并嘧啶-4-胺的合成新方法.以相对廉价的2,5-二羟基-1,4-二噻烷和丙二腈为原料,依次通过Gewald反应、芳环溴代、缩合、环合以及Dimroth重排四步反应得到目标产物6-溴-N-3-氯-4-(3-氟苄氧基)苯基]噻吩2,3-d]并嘧啶-4-胺,总产率为56.9%.用1H NMR,IR,MS和HRMS对产物进行了结构表征.并应用该方法,合成了一系列的6-溴-N-芳基噻吩2,3-d]并嘧啶-4-胺类化合物.研究表明该方法具有原料易得、操作简便、收率较高,且产物容易分离纯化等优点.
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| 关 键 词： | 噻吩[2 3-d]并嘧啶 Dimroth重排 合成方法 机理 |
A Novel Synthetic Method for 6-Bromo-N-arylthieno[2,3-d]-pyrimidin-4-amines |
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| Zhan Dongmei,Li Siyuan,Zhao Hongli,Lan Minbo.A Novel Synthetic Method for 6-Bromo-N-arylthieno[2,3-d]-pyrimidin-4-amines[J].Chinese Journal of Organic Chemistry,2011,31(2). |
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| Authors: | Zhan Dongmei Li Siyuan Zhao Hongli Lan Minbo |
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| Institution: | Zhan,Dongmeia Li,Siyuana Zhao,Honglia Lan,Minbo*,a,b(a Shanghai Key Laboratory of Functional Materials Chemistry,and Research Centre of Analysis and Test,East China University of Science and Technology,Shanghai 200237)(b State Key Laboratory of Bioreactor Engineering,Shanghai 200237) |
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| Abstract: | In this paper,a novel synthetic method for 6-bromo-N-3-chloro-4-(3-fluorobenzyloxy)phenyl]-thienopyrimidin-4-amine was reported,which began from cheap 2,5-dihydroxy-1,4-dithiane and malononitrile,following Gewald reaction,aromatic ring bromonation,condensation,cyclization and then Dimroth rearrangement reaction.The over yield was 56.9%.The structures of synthesized compounds were determined by 1H NMR,IR,MS and HRMS techniques.Employing the same synthetic method,a series of 6-bromo-N-arylthienopyrimidin-4-a... |
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| Keywords: | thienopyrimidines Dimroth rearrangement synthetic method mechanism |
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