Direct synthesis of 2-methylpyridines via I2-triggered [3 + 2 + 1] annulation of aryl methyl ketoxime acetates with triethylamine as the carbon source

A facile and efficient [3 + 2 + 1] annulation of aryl methyl ketoxime acetates and triethylamine for the synthesis of 2-methylpyridines was disclosed. This reaction demonstrated that I2 was effective in triggering N–O bond cleavage of oxime acetates generating imine radicals. It was noteworthy that...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2018, Vol.16 (13), p.2342-2348
Main Authors: Gao, Qinghe, Yan, Huijuan, Wu, Manman, Sun, Jiajia, Yan, Xiqing, Wu, Anxin
Format: Article
Language:English
Subjects:
Acetates
Acetic acid
Aromatic compounds
Carbon sources
Chemical reactions
Chemical synthesis
Organic chemistry
Pyridines
Triethylamine
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Summary:A facile and efficient [3 + 2 + 1] annulation of aryl methyl ketoxime acetates and triethylamine for the synthesis of 2-methylpyridines was disclosed. This reaction demonstrated that I2 was effective in triggering N–O bond cleavage of oxime acetates generating imine radicals. It was noteworthy that this transformation employed triethylamine as the carbon source for the direct formation of pyridines and introduction of methyl groups.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob00349a