Synthesis of 1,3-Dicarbonyl Azepines via Photoinitiated Reactions of Aryl Azides with Carbon-Based Nucleophiles

A photoinduced one-pot method for the synthesis of azepines by the reaction of aryl azides with 1,3-dicarbonyl compounds under weakly basic conditions is described. This method offers a simple route for the synthesis of 1,3-dicarbonyl-substituted azepines in good to excellent yields and high regiose...

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Published inJournal of organic chemistry Vol. 89; no. 14; pp. 10283 - 10292
Main Authors Giricheva, Marina A., Vorobiev, Ivan G., Belikov, Alexey A., Fukin, Georgy K., Budruev, Andrei V.
Format Journal Article
LanguageEnglish
Published American Chemical Society 19.07.2024
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Summary:A photoinduced one-pot method for the synthesis of azepines by the reaction of aryl azides with 1,3-dicarbonyl compounds under weakly basic conditions is described. This method offers a simple route for the synthesis of 1,3-dicarbonyl-substituted azepines in good to excellent yields and high regioselectivity and was tested on 1,3-dicarbonyl compounds with different acidity levels. The resulting azepines have electrophilic and nucleophilic centers of varying degrees of activity, which facilitate reactions leading to further structural transformations.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c01177