Issue 8, 2023

TBHP-promoted multicomponent reaction to access 2-aminobenzoxazinones using sodium chlorodifluoroacetate as the C1 synthon

Abstract

A tert-butyl hydroperoxide-promoted multicomponent reaction of isatins, sodium chlorodifluoroacetate, and aliphatic amines has been disclosed. This reaction provides a facile and practical approach for producing functionalized 2-aminobenzoxazinones under transition-metal-free conditions. The preliminary mechanism indicates that the reaction probably proceeds through an intermolecular cyclization process between isatoic anhydride and imine cation intermediates. Notably, the carbon atom at the 2-position of the benzoxazinone ring originated from an unusual quadruple cleavage of sodium chlorodifluoroacetate.

Graphical abstract: TBHP-promoted multicomponent reaction to access 2-aminobenzoxazinones using sodium chlorodifluoroacetate as the C1 synthon

Supplementary files

Article information

Article type
Research Article
Submitted
01 Feb 2023
Accepted
07 Mar 2023
First published
08 Mar 2023

Org. Chem. Front., 2023,10, 1988-1993

TBHP-promoted multicomponent reaction to access 2-aminobenzoxazinones using sodium chlorodifluoroacetate as the C1 synthon

H. Li, Y. Wang, C. Xu, J. Zou, Y. Wu and G. Yin, Org. Chem. Front., 2023, 10, 1988 DOI: 10.1039/D3QO00157A

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