7340-01-4Relevant articles and documents
A Cascade Process of Hydroxamates Renders 1,6-Dioxa-3,9-diazaspiro[44]nonane-2,8-diones
Nazarian, Zohreh,Forsyth, Craig M.
, p. 2081 - 2091 (2021/02/01)
A cascade route to 1,6-dioxa-3,9-diazaspiro[4.4]nonane-2,8-diones from N, O -diacyl hydroxylamines consisting of a two-step procedure is described. The key transformation is a [3,3]-sigmatropic rearrangement of N, O -diacyl hydroxylamines promoted by form
Base-promoted aromatic [3,3] sigmatropic rearrangement of N-acyl-O-arylhydroxylamine derivatives
Tayama, Eiji,Hirano, Kazuki
, p. 665 - 673 (2019/01/04)
The base-promoted aromatic [3,3] sigmatropic rearrangement of N-acyl-O-arylhydroxylamines giving α-(2-hydroxyphenyl)amides was successfully demonstrated. The substrates were prepared from N-substituted hydroxylamines by N-acylation followed by copper(I)-mediated O-arylation with boronic acids. Treatment of the substrates with lithium hexamethyldisilazide (LiHMDS) in THF at 0 °C to room temperature generated the corresponding amide enolates. The aromatic [3,3] rearrangement of the enolates provided the desired products in moderate to good yields. A crossover experiment produced only intramolecular products and clarified that the reaction proceeds via the aromatic [3,3] sigmatropic rearrangement, not a bond-cleavage–recombination process. Our method is a formal α-arylation of amides.
Reductive cleavage of N-O bonds in hydroxylamines and hydroxamic acid derivatives using samarium diiodide
Keck, Gary E.,Wager, Travis T.,McHardy, Stanton F.
, p. 11755 - 11772 (2007/10/03)
An efficient process for the reductive cleavage of N-O bonds using samarium diiodide is detailed for a variety of structural types to define the scope and limitations of the method. The reduction is shown to be compatible with base sensitive substrates such as trifluoroacetamide derivatives, which cannot be reduced satisfactorily using aluminum amalgam or sodium amalgam. Direct quenching of the reduction mixture with acylating agents is demonstrated to provide high yields of protected amines in a one-pot process from the N-O derivatives.