Synthesis of imidazo[1, 5-a]pyridines via I2-mediated sp3 C–H amination. Issue 31 (24th July 2018)

• Record Type: Journal Article
• Authors: Hu, Zhiyuan; Hou, Jiao; Liu, Jie; Yu, Wenquan; Chang, Junbiao
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 31(2018)
• Page Start: 5653
• Page End: 5660
• Publication Date: 2018-07-24
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob01501e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A transition-metal-free sp 3 C–H amination reaction has been developed employing molecular iodine for imidazo[1, 5- a ]pyridine synthesis. Abstract : 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 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.