Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 16, Issue 31, Pages 5653-5660Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8ob01501e
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Funding
- National Natural Science Foundation of China [81773570, 81330075]
- Outstanding Young Talent Research Fund of Zhengzhou University [1521316004]
- College Students' Innovation and Entrepreneurship Training Program of Zhengzhou University [2017cxcy053]
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A transition-metal-free sp(3) 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 I-2-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.
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