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Poudel, Tej Narayan,Karanjit, Sangita,Khanal, Hari Datta,Tamargo, Ramuel John Inductivo,Lee, Yong Rok American Chemical Society 2018 ORGANIC LETTERS Vol.20 No.18
<P>An efficient synthesis of highly π-extended carbazoles is described via an unexpected domino [5 + 3 + 1] annulation approach. The Cu(I)-/base-promoted reactions of 2-nitrocinnamaldehydes with benzyl cyanides provide diverse benzo[<I>b</I>]carbazoles. The reaction is proposed to proceed via a sequential Michael addition/intramolecular addition of an enol into a nitro group, 6π- electrocyclization, and the final oxidative aromatization as supported by density functional theory calculations. Some of the synthesized carbazoles showed significant potential in fluorescence sensing of Cu<SUP>2+</SUP> ions.</P> [FIG OMISSION]</BR>