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

Authors :
Liu S
Wang AJ
Li M
Zhang J
Yin GD
Shu WM
Yu WC
Source :
The Journal of organic chemistry [J Org Chem] 2022 Aug 19; Vol. 87 (16), pp. 11253-11260. Date of Electronic Publication: 2022 Aug 08.
Publication Year :
2022

Abstract

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.

Details

Language :
English
ISSN :
1520-6904
Volume :
87
Issue :
16
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
35938613
Full Text :
https://doi.org/10.1021/acs.joc.2c01214