An Expedient Synthesis of 2-Aryl-1,4-benzoxazin-3-ones via Tandem Anionic Cyclisation/Alkylation Reactions of N-Boc-O-benzyl-2-aminophenols

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...

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Bibliographic Details
Published in:Synlett 2016-11, Vol.13 (4), p.471-474
Main Authors: Bodero, Olga, Spivey, Alan C.
Format: Article
Language:English
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Summary: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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0036-1588348