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Cu(I)-/Base-Mediated Domino [5 + 3 + 1] Annulation for Highly π-Extended Carbazole Frameworks and DFT Mechanistic
Tej Narayan Poudel1, Sangita Karanjit2, Hari Datta Khanal1
1School of Chemical Engineering , Yeungnam University , Gyeongsan 38541 , Republic of Korea.
Abstract:
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[ b]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 Cu2+ ions.
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