Efficient one-pot synthesis of highly substituted pyridin-2(1H)-ones via the Vilsmeier-Haack reaction of 1-acetyl,1-carbamoyl cyclopropanes

A facile and efficient one-pot synthesis of highly substituted pyridin-2(1H)-ones is developed via the Vilsmeier-Haack reaction of readily available 1-acetyl,1-carbamoyl cyclopropanes, and a mechanism involving sequential ring-opening, haloformylation, and intramolecular nucleophilic cyclization rea...

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Bibliographic Details
Published in:Organic letters Vol. 9; no. 12; pp. 2421 - 2423
Main Authors: Pan, Wei, Dong, Dewen, Wang, Kewei, Zhang, Jie, Wu, Rigenhada, Xiang, Dexuan, Liu, Qun
Format: Journal Article
Language:English
Published: WASHINGTON Amer Chemical Soc 07.06.2007
Subjects:
Chemistry
Chemistry, Organic
Crystallography, X-Ray
Cyclopropanes - chemistry
Models, Molecular
Molecular Structure
Physical Sciences
Pyridones - chemical synthesis
Pyridones - chemistry
Science & Technology
Stereoisomerism
CYCLOADDITION
PYRIDINE RINGS
STRATEGY
2-PYRIDONE
INHIBITORS
DERIVATIVES
PYRIDONES
ISSN:1523-7060
Online Access:Get more information
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Summary:A facile and efficient one-pot synthesis of highly substituted pyridin-2(1H)-ones is developed via the Vilsmeier-Haack reaction of readily available 1-acetyl,1-carbamoyl cyclopropanes, and a mechanism involving sequential ring-opening, haloformylation, and intramolecular nucleophilic cyclization reactions is proposed.
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ISSN:1523-7060
DOI:10.1021/ol070905i