Annulation-Triggered Denitrogenative Transformations of 2‑(5-Iodo-1,2,3-triazolyl)benzoic Acids

The ability of [1,2,3]­triazolobenzoxazinones to act as a source of “hidden” diazo group was discovered. These diazo precursors can be easily prepared by the intramolecular cyclization of 2-(5-iodo-1,2,3-triazolyl)­benzoic acids. The Cu-catalyzed capture of the hidden diazo group allows for further...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-06, Vol.87 (11), p.7064-7075
Main Authors: Voloshkin, Vladislav A., Kotovshchikov, Yury N., Latyshev, Gennadij V., Lukashev, Nikolay V., Beletskaya, Irina P.
Format: Article
Language:English
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Summary:The ability of [1,2,3]­triazolobenzoxazinones to act as a source of “hidden” diazo group was discovered. These diazo precursors can be easily prepared by the intramolecular cyclization of 2-(5-iodo-1,2,3-triazolyl)­benzoic acids. The Cu-catalyzed capture of the hidden diazo group allows for further functionalization through the denitrogenative pathway. The transformations proceed via the formation of either diazoimine or diazoamide intermediates. Novel routes to various anthranilamides as well as thiolated benzoxazinones were developed using the one-pot cyclization/diazo capture procedure.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c00235