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

Shan Liu, An-Jing Wang, Min Li, Jing Zhang, Guo-Dong Yin, Wen-Ming Shu* and Wei-Chu Yu*

*College of Chemistry and Environmental Engineering, Yangtze University, Jingzhou 434023, PR China, Email: shuwmyangtzeu.edu.cn, yuweichu126.com

S. Liu, A.-J. Wang, M. Li, J. Zhang, G.-D. Yin, W.-M. Shu, W.-C. Yu, J. Org. Chem., 2022, 87, 11253-11260.

DOI: 10.1021/acs.joc.2c01214


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Abstract

A Rh(III)-catalyzed tandem reaction of 2,1-benzisoxazoles with α-azido ketones provides (quinazolin-2-yl)methanone derivatives via denitrogenation of the α-azido ketones, aza-[4 + 2] cycloaddition, ring opening, and dehydration aromatization processes.

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proposed mechanism



Key Words

Quinazolines


ID: J42-Y2022