Rapid construction of acridines via BF3•Et2O promoted cyclization of 2-phenylamino benzophenones

[Display omitted] A concise and practical strategy for the rapid construction of acridines from 2-phenylamino benzophenone promoted by BF3•Et2O has been developed. The reaction goes through the intramolecular Friedel–Crafts acylation and dehydration with a facile work-up procedure. It shows good fun...

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Veröffentlicht in:Tetrahedron letters 2022-08, Vol.105, p.154044, Article 154044
Hauptverfasser: Deng, Liuyang, Guo, Ranran, Wang, Lianjie, Yang, Cao, Wang, Zechao
Format: Artikel
Sprache:eng
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Zusammenfassung:[Display omitted] A concise and practical strategy for the rapid construction of acridines from 2-phenylamino benzophenone promoted by BF3•Et2O has been developed. The reaction goes through the intramolecular Friedel–Crafts acylation and dehydration with a facile work-up procedure. It shows good functional group tolerance and the yields of acridines are mostly in range of 90–99 %. The efficiency of this reaction is tremendously high, which can be completed within 30 min. Gram-scale synthesis and synthetic application experiment illustrate the practical utility of the method as a synthetic tool. Photoluminescence spectra indicate these acridines are promising candidates for OLEDs and make this new methodology great potentials in materials.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2022.154044