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The Rearrangement of Peroxides for the Construction of Fluorophoric 1,4-Benzoxazin-3-one Derivatives

Author:
Chaudhari, Moreshwar B., Chaudhary, Atul, Kumar, Vishnupriya, Gnanaprakasam, Boopathy
Source:
Organic letters 2019 v.21 no.6 pp. 1617-1621
ISSN:
1523-7052
Subject:
catalysts, chemical bonding, chemical reactions, chemical structure, cleavage (chemistry), ferric chloride, organic compounds, peroxides, tin
Abstract:
An unprecedented skeletal rearrangement of 3-(tert-butylperoxy)indolin-2-one using a tin catalyst has been developed. This rearrangement is highly selective to afford a series of fluorophoric (Z)-2-arylidene and alkylidene-2H-benzo[b][1,4]oxazin-3(4H)-one derivatives in good to excellent yield. In contrast with Sn(OTf)₂, the reaction of 3-(tert-butylperoxy)indolin-2-one derivatives with FeCl₃ afforded the Hock fragmentation product via C–C bond cleavage.
Agid:
6326786