Sequential Ring-Opening and Ring-Closing Reactions for Converting para-Substituted Pyridines into meta-Substituted Anilines

Herein we report a method for converting para-substituted pyridine rings into meta-dialkylamino-substituted benzene rings through sequential ring-opening and ring-closing reactions. The nitrogen atom in the pyridine rings was replaced with a methine group, and a dialkylamino substituent was introduc...

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Bibliographic Details
Published in:Organic letters Vol. 23; no. 15; pp. 6126 - 6130
Main Authors: Morofuji, Tatsuya, Inagawa, Kota, Kano, Naokazu
Format: Journal Article
Language:English
Published: American Chemical Society 06-08-2021
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Summary:Herein we report a method for converting para-substituted pyridine rings into meta-dialkylamino-substituted benzene rings through sequential ring-opening and ring-closing reactions. The nitrogen atom in the pyridine rings was replaced with a methine group, and a dialkylamino substituent was introduced onto the original unsubstituted carbon atom in the pyridine rings. This process can be formally regarded as a hybrid of the skeletal editing and C–H amination of pyridine rings.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c02225