Visible-light-promoted decarboxylative addition cyclization of -aryl glycines and azobenzenes to access 1,2,4-triazolidines

Methods for the synthesis of 1,2,4-triazolidines are scarce. Herein, we report a visible-light-promoted decarboxylative addition cyclization of N -aryl glycines and azobenzenes to access such important compounds. Using commercially available methylene blue (MB) as an organic photocatalyst, the react...

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Veröffentlicht in:Green chemistry : an international journal and green chemistry resource : GC 2021-08, Vol.23 (16), p.586-5811
Hauptverfasser: Yang, Jingya, Song, Menghui, Zhou, Hongyan, Qi, Yanfang, Ma, Ben, Wang, Xi-Cun
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Zusammenfassung:Methods for the synthesis of 1,2,4-triazolidines are scarce. Herein, we report a visible-light-promoted decarboxylative addition cyclization of N -aryl glycines and azobenzenes to access such important compounds. Using commercially available methylene blue (MB) as an organic photocatalyst, the reaction proceeded smoothly in the absence of transition-metal catalysts at ambient temperature, affording the corresponding products, 1,2,4-triaryl 1,2,4-triazolidines, in good to excellent yields. This work demonstrates a new synthetic application of readily available azobenenes and provides a novel strategy for constructing 1,2,4-triazolidines. Direct synthesis of 1,2,4-triazolidines have been readily achieved by the visible-light-promoted reaction of N -aryl glycines and azobenzenes under mild conditions.
ISSN:1463-9262
1463-9270
DOI:10.1039/d1gc02272e