TBHP-promoted multicomponent reaction to access 2-aminobenzoxazinones using sodium chlorodifluoroacetate as the C1 synthon?
Organic Chemistry Frontiers Pub Date: 2023-03-08 DOI: 10.1039/D3QO00157A
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.
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Journal Name：Organic Chemistry Frontiers
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CAS no.: 89640-58-4
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