Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 10, Issue 7, Pages 1786-1794Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202100258
Keywords
Ruthenium (VIII); Oxidative dearomatization; N-alkyl-2-pyridone; Pyridinium salt
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Funding
- Department of Science and Technology (DST), Govt. of India [EEQ/2016/000518, EEQ/2020/000463, TTR/2020/000015]
- NIT, Rourkela
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This study describes an efficient synthetic strategy using pyridyl C-X activation to generate N-alkyl-2-pyridones from N-alkyl-2-halopyridinium salts. The strategy involves an in-situ generation of Ru(VIII) for catalytic dearomative synthesis of pyridones, which can be further reduced to N-alkyl-2-piperidones. A plausible mechanism is proposed based on controlled reactions.
An efficient synthetic strategy employing pyridyl C-X activation, for the generation of N-alkyl-2-pyridones from N-alkyl-2-halopyridinium salts is described. As pyridones are dearomatised synthetic derivatives of pyridines, a versatile scope exist for pyridyl C-H functionalisation. The present strategy exemplifies a straight forward in-situ generation of Ru(VIII), leading catalytic dearomative synthesis of pyridones. The N-alkyl-2-pyridones are further reduced to N-alkyl-2-piperidones and a plausible mechanism is also drawn, which is supported by some controlled reactions.
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