A novel and convenient method for the preparation of 5-(diphenylmethylene)-1H-pyrrol-2(5H)-ones; synthesis and mechanistic study

作者：Faigl Ferenc; Deak Szilvia; Mucsi Zoltan; Hergert Tamas; Balazs Laszlo; Sandor Boros; Balazs Barbara; Holczbauer Tamas; Nyerges Miklos; Matravolgyi Bela^*

来源：Tetrahedron, 2016, 72(35): 5444-5455.

DOI：10.1016/j.tet.2016.07.032

• 5-Ylidenepyrrol-2(5H)-one
• Bromopyrrole
• Butyllithium
• Mechanistic study
• X-ray crystallography

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.

• 出版日期2016-9-1
• 单位河北医科大学