Synthesis of 1,4-dihydro-benzo[ d][1,3]oxazin-2-ones from phthalides via an aminolysis-Hofmann rearrangement protocol

A two-step procedure for the synthesis of benzoxazinones from phthalides was developed. A simple two-step procedure for the conversion of readily available phthalides to the corresponding benzoxazinones was developed. Initial ring-opening aminolysis to form a primary 2-hydroxymethylbenzamide, follow...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2007-12, Vol.48 (51), p.8972-8975
Main Authors: Hernández, Eliud, Vélez, Jessica M., Vlaar, Cornelis P.
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A two-step procedure for the synthesis of benzoxazinones from phthalides was developed. A simple two-step procedure for the conversion of readily available phthalides to the corresponding benzoxazinones was developed. Initial ring-opening aminolysis to form a primary 2-hydroxymethylbenzamide, followed by reaction with bis(trifluoroacetoxy)iodobenzene (BTI) conveniently, provided a variety of 4-substituted benzoxazinones.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.10.114