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Issue 9, 2018
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Transition-metal-free C–N and C–C formation: synthesis of benzo[4,5]imidazo[1,2-a]pyridines and 2-pyridones from ynones

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Abstract

Herein, a transition metal-free and efficient cascade reaction of ynones with 2-methylbenzimidazoles under mild conditions has been revealed. This cascade reaction involved a Michael addition/intramolecular cycloaddition/dehydration and provided the desired benzo[4,5]imidazo[1,2-a]pyridines in moderate to good yield. Furthermore, three benzo[4,5]imidazo[1,2-a]pyridines (3d, 3i, and 3q) exhibited good activities against Hep-G2 (human liver cancer), T-24 (human bladder cancer cell), and SK-OV-3 (human ovarian cancer) cell lines with IC50 values in the range of 8.05–10.67 μmol L−1. To investigate the mechanism of the effective inhibition of cell growth, further studies, including cell cycle analysis, apoptosis ratio detection, measurement of Ca2+ generation, ROS, mitochondrial membrane potential assay, and caspase-3/9 activation, were carried out on compound 3i.

Graphical abstract: Transition-metal-free C–N and C–C formation: synthesis of benzo[4,5]imidazo[1,2-a]pyridines and 2-pyridones from ynones

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Publication details

The article was received on 08 Jan 2018, accepted on 08 Mar 2018 and first published on 09 Mar 2018


Article type: Paper
DOI: 10.1039/C8GC00069G
Citation: Green Chem., 2018,20, 2007-2012
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    Transition-metal-free C–N and C–C formation: synthesis of benzo[4,5]imidazo[1,2-a]pyridines and 2-pyridones from ynones

    Q. Teng, X. Peng, Z. Mo, Y. Xu, H. Tang, H. Wang, H. Sun and Y. Pan, Green Chem., 2018, 20, 2007
    DOI: 10.1039/C8GC00069G

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