无催化剂条件下的全氟烷基取代的1H-苯并[b][1,4]二氮?-2(3H)-酮的简易合成
收稿日期: 2012-10-19
修回日期: 2012-11-18
网络出版日期: 2012-11-23
Facile Synthesis of Perfluoroalkyl Substituted 1,5-Benzodiazepine-2-ones via a Catalyst-free Process
Received date: 2012-10-19
Revised date: 2012-11-18
Online published: 2012-11-23
Supported by
Project supported by the National Natural Science Foundation of China (Grant Nos. 21072126 and 21272152) and the Leading Academic Discipline Projects of Shanghai Municipal Education Commission (Grant No. J50102).
1,5-苯并二氮?-2-酮作为一个独特的骨架广泛存在于很多具有生理活性的化合物中, 而全氟烷基的引入常可影响到有机化合物的理化性质以及生理活性的改变。因此将全氟代烷基引入1,5-苯并二氮?-2-酮的方法的研究正变得日趋重要。本文发展了一个制备全氟代烷基取代的1,5-苯并二氮?-2-酮的简易方法。采用全氟代炔酸甲酯为含氟砌块, 与邻芳基二胺, 以无水甲苯为溶剂, 在无催化剂存在条件下, 80℃反应24 h, 以较好的收率顺利得到4-全氟烷基-1,3-二氢-1,5-苯并二氮?-2-酮类化合物。
关键词： 全氟烷基; 1,5-苯并二氮?-2-酮; 全氟烷基炔酸甲酯; 邻芳基二胺
翟士燕 , 曹卫国 , 张慧 . 无催化剂条件下的全氟烷基取代的1H-苯并[b][1,4]二氮?-2(3H)-酮的简易合成[J]. 有机化学, 0 , (0) : 0 -0 . DOI: 10.6023/cjoc201210037
1,5-Benzodiazepin-2-one is a privileged scaffold and compounds containing such substructures exhibit a range of biological activities. Perfluoroalkyl groups can favorably affect the physical and biological properties of organic compounds. Accordingly, the development of methods to introduce perfluoroalkyl groups into 1,5-benzodiazepin-2-ones has become increasingly important. Herein, an ef?cient and simple route for preparation of perfluoroalkylated 1,5-benzodiazepine-2-ones is described. The reaction of methyl 3-perfluoroalkyl-2-alkynoate as the fluorinated building block with o-arylenediamine proceeds smoothly in dry toluene at 80 ℃ for 24 h without any catalyst to afford the titled compounds in good yields.
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