文献类型：期刊文献

中文题名：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

英文题名：A Novel Synthetic Method for 6-Bromo-N-arylthieno[2,3-d]-pyrimidin-4-amines

作者：詹冬梅[1];李思远[1];赵红莉[1];蓝闽波[1,2]

机构：[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]华东理工大学生物反应器工程国家重点实验室,上海200237

年份：2011

卷号：31

期号：2

起止页码：207

中文期刊名：有机化学

外文期刊名：Chinese Journal of Organic Chemistry

收录：CSTPCD;;Scopus;北大核心:【北大核心2008】；CSCD:【CSCD2011_2012】；

基金：上海市科委(No.10dz2220500)资助项目

语种：中文

中文关键词：噻吩[2,3-d]并嘧啶;Dimroth重排;合成方法;机理

外文关键词：thienopyrimidines; Dimroth rearrangement; synthetic method; mechanism

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.
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-amine derivatives were synthesized.The results showed that the advantages of this method were simply available starting meterials,easily conducted procedure,relatively high yield,and easily purification of the products.