An expedient synthesis of 2-aryl-1,4-benzoxazin-3-ones via tandem Anionic cyclisation/alkylation reactions of N-Boc-O-benzyl-2-aminophenols

File Description SizeFormat 
Synlett - benzoxazinones Mk4 FINAL REVISED.pdfAccepted version1.12 MBAdobe PDFView/Open
Title: An expedient synthesis of 2-aryl-1,4-benzoxazin-3-ones via tandem Anionic cyclisation/alkylation reactions of N-Boc-O-benzyl-2-aminophenols
Authors: Bodero, O
Spivey, AC
Item Type: Journal Article
Abstract: A one-pot, tandem anionic cyclization/alkylation reaction of N-Boc-O-benzylated-2-aminophenols to give 2-aryl-1,4-benzoxazin-3-ones is described. The Boc protecting group plays a crucial role in the process, as the tert-butoxide liberated in the cyclisation step facilitates the benzylic deprotonation necessary for the subsequent alkylation. The reaction gives expedient access to a range of substitution patterns in 1,4-benzoxazin-3-ones of potential biological relevance.
Issue Date: 24-Nov-2016
Date of Acceptance: 18-Oct-2016
URI: http://hdl.handle.net/10044/1/43004
DOI: https://dx.doi.org/10.1055/s-0036-1588348
ISSN: 0936-5214
Publisher: Thieme Publishing
Journal / Book Title: Synlett
Volume: 27
Copyright Statement: © 2016 Georg Thieme Verlag Stuttgart. The published online version is available at https://dx.doi.org/10.1055/s-0036-1588348
Sponsor/Funder: Commission of the European Communities
Funder's Grant Number: PIEF-GA-2012-327114
Keywords: Organic Chemistry
0305 Organic Chemistry
Publication Status: Published
Appears in Collections:Chemistry
Faculty of Natural Sciences



Items in Spiral are protected by copyright, with all rights reserved, unless otherwise indicated.

Creative Commons