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Issue 31, 2018
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Synthesis of imidazo[1,5-a]pyridines via I2-mediated sp3 C–H amination

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Abstract

A transition-metal-free sp3 C–H amination reaction has been established for imidazo[1,5-a]pyridine synthesis employing molecular iodine from 2-pyridyl ketones and alkylamines. In the presence of sodium acetate (NaOAc), the I2-mediated oxidative annulations of readily available substrates produced a variety of imidazo[1,5-a]pyridine derivatives efficiently in a one-pot manner. The present synthetic approach is operationally simple and can be conveniently carried out on a gram scale. Moreover, under the optimal reaction conditions a series of 1-(2-pyridyl)imidazo[1,5-a]pyridine cysteine protease inhibitors were easily prepared from the corresponding di-2-pyridyl ketones and substituted benzylamines in satisfactory yields.

Graphical abstract: Synthesis of imidazo[1,5-a]pyridines via I2-mediated sp3 C–H amination

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Publication details

The article was received on 25 Jun 2018, accepted on 16 Jul 2018 and first published on 17 Jul 2018


Article type: Paper
DOI: 10.1039/C8OB01501E
Citation: Org. Biomol. Chem., 2018,16, 5653-5660
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    Synthesis of imidazo[1,5-a]pyridines via I2-mediated sp3 C–H amination

    Z. Hu, J. Hou, J. Liu, W. Yu and J. Chang, Org. Biomol. Chem., 2018, 16, 5653
    DOI: 10.1039/C8OB01501E

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