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  • Title: One-pot synthesis of highly fluorescent pyrido[1,2-a]indole derivatives through C-H/N-H activation: photophysical investigations and application in cell imaging.
    Author: Samala S, Pallavi P, Kumar R, Arigela RK, Singh G, Ampapathi RS, Priya A, Datta S, Patra A, Kundu B.
    Journal: Chemistry; 2014 Oct 27; 20(44):14344-50. PubMed ID: 25213659.
    Abstract:
    We describe a straightforward strategy for the synthesis of strongly fluorescent pyridoindoles by Pd-catalyzed oxidative annulations of internal alkynes with C-3 functionalized indoles through CH/NH bond activation in a one-pot tandem process. Mechanistic investigations reveal the preferential activation of NH indole followed by CH activation during the cyclization process. Photophysical properties of pyridoindoles exhibited the highest fluorescence quantum yield of nearly 80 %, with emission color varying from blue to green to orange depending on the substructures. Quantum mechanical calculations provide insights into the observed photophysical properties. The strong fluorescence of the pyrido[1,2-a]indole derivative has been employed in subcellular imaging, which demonstrates its localization in the cell nucleus.
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