This paper describes a novel strategy for the synthesis of 2,3,4-trisubstituted pyridines via organocatalyzed three-component reactions. A variety of pyridine derivatives are synthesized from readily available ketones with α,β-unsaturated aldehydes and ammonium acetate under a mild organocatalyst. This protocol leads to rapid N-annulation through C-C and C-N bond formation in a single operation, thereby avoiding the preparation of essential functional groups, such as oximes, imines, or azides. The synthesized compounds are used for the evaluation of antibacterial activities and as fluorescence sensors for Cu(2+) ions.
Photoluminescent detection and imaging of Hg2+ ions in the biochemical living system are of great importance. In this study, a new photoluminescent probe based on nitrogen (N), sulfur (S), and...
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 Cu ions.
An efficient Rh(iii)-catalyzed annulation of arylamides with 3-diazoquinolinediones for the construction of diverse and highly functionalized isochromenoquinolinedione derivatives is described.
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