Rh(III)-Catalyzed Tandem Reaction Access to (Quinazolin-2-yl)methanone Derivatives from 2,1-Benzisoxazoles and α‑Azido Ketones

A Rh­(III)-catalyzed tandem reaction for the synthesis of (quinazolin-2-yl)­methanone derivatives has been explored from 2,1-benzisoxazoles and α-azido ketones. The transformation involves Rh­(III)-catalyzed denitrogenation of α-azido ketones, aza-[4 + 2] cycloaddition, ring opening, and dehydration...

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Veröffentlicht in:Journal of organic chemistry 2022-08, Vol.87 (16), p.11253-11260
Hauptverfasser: Liu, Shan, Wang, An-Jing, Li, Min, Zhang, Jing, Yin, Guo-Dong, Shu, Wen-Ming, Yu, Wei-Chu
Format: Artikel
Sprache:eng
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Zusammenfassung:A Rh­(III)-catalyzed tandem reaction for the synthesis of (quinazolin-2-yl)­methanone derivatives has been explored from 2,1-benzisoxazoles and α-azido ketones. The transformation involves Rh­(III)-catalyzed denitrogenation of α-azido ketones, aza-[4 + 2] cycloaddition, ring opening, and dehydration aromatization processes. Notably, the aza-[4 + 2] cycloaddition of an imine rhodium complex intermediate with 2,1-benzisoxazoles is the key to this reaction.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01214