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J Org Chem. 2019 Apr 24. doi: 10.1021/acs.joc.9b00208. [Epub ahead of print]

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

Author information

1
Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Center for Fine Chemicals , Guizhou University , Huaxi District, Guiyang 550025 , China.

Abstract

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.

PMID:
30977657
DOI:
10.1021/acs.joc.9b00208

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