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A novel and convenient method for the preparation of 5-(diphenylmethylene)-1H-pyrrol-2(5H)-ones; synthesis and mechanistic study
Tetrahedron ( IF 2.1 ) Pub Date : 2016-07-09 , DOI: 10.1016/j.tet.2016.07.032
Ferenc Faigl , Szilvia Deák , Zoltán Mucsi , Tamás Hergert , László Balázs , Boros Sándor , Barbara Balázs , Tamás Holczbauer , Miklós Nyerges , Béla Mátravölgyi

An efficient, regioselective synthesis has been developed for the preparation of 5-(diphenylmethylene)-1H-pyrrol-2(5H)-ones from readily available 1H-pyrroles by sequential dibromination and selective organometallic bromine/lithium exchange followed by reaction with benzophenone. Comparison of various N-substituents was shown to demonstrate the high tolerance of the transformation to functional groups. The structures of the new products were determined by spectroscopic methods and confirmed by single-crystal X-ray diffraction measurement. In addition, theoretical study of the reaction mechanism and selective functionalization of the endocyclic double bond were also presented.



中文翻译:

一种新颖且方便的制备5-(二苯基亚甲基)-1 H-吡咯-2(5 H)-的方法;综合与机理研究

通过顺序二溴化和选择性有机金属溴/锂交换随后反应,已经开发了一种有效的区域选择性合成方法,用于从易于获得的1 H-吡咯中制备5-(二苯基亚甲基)-1 H-吡咯-2(5 H)-酮。与二苯甲酮。各种N-取代基的比较显示出对转化为官能团的高耐受性。通过光谱法确定新产物的结构,并通过单晶X射线衍射测量证实。此外,还对环内双键的反应机理和选择性官能化进行了理论研究。

更新日期:2016-07-09
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