Issue 31, 2018

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

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

Supplementary files

Article information

Article type
Paper
Submitted
25 Jun 2018
Accepted
16 Jul 2018
First published
17 Jul 2018

Org. Biomol. Chem., 2018,16, 5653-5660

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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