Diverse Oxidative C(sp2)–N Bond Cleavages of Aromatic Fused Imidazoles for Synthesis of α‑Ketoamides and N‑(pyridin-2-yl)arylamides

An efficient and chemoselective C­(sp2)–N bond cleavage of aromatic imidazo­[1,2-a]­pyridine molecules is developed. A broad scope of amide compounds such as α-ketoamides and N-(pyridin-2-yl)­arylamides are afforded as the final products in up to quantitative yields. Diverse C–N bond cleavages are c...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-07, Vol.84 (13), p.8411-8422
Main Authors: Xu, Fangzhou, Wang, Yanyan, Xun, Xiwei, Huang, Yun, Jin, Zhichao, Song, Baoan, Wu, Jian
Format: Article
Language:English
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Summary:An efficient and chemoselective C­(sp2)–N bond cleavage of aromatic imidazo­[1,2-a]­pyridine molecules is developed. A broad scope of amide compounds such as α-ketoamides and N-(pyridin-2-yl)­arylamides are afforded as the final products in up to quantitative yields. Diverse C–N bond cleavages are controlled by the oxidative species used in this transformation, with various amide products afforded in a chemoselective fashion. A preliminary study indicated that some α-ketoamides exhibit anti-Tobacco Mosaic Virus activity for potential use in plant protection.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b00208