24810-46-6Relevant academic research and scientific papers
Pd-catalyzed assembly of spirooxindole natural products: A short synthesis of horsfiline
Deppermann, Nina,Thomanek, Heike,Prenzel, Alexander H. G. P.,Maison, Wolfgang
experimental part, p. 5994 - 6000 (2010/12/19)
The Pd-catalyzed intramolecular α-arylation of amides is applied to the synthesis of functionalized spirooxindoles. The substrate scope is evaluated, and the reaction is demonstrated to be useful for the assembly of spirooxindole natural products and derivatives thereof. As an application, a new synthesis of horsfiline 1 is presented, giving the natural product in only 4 steps from commercially available amino acid 12.
Azirine/oxindole ring enlargement via amidinium intermediates
Mekhael, Maged K. G.,Bienz, Stefan,Linden, Anthony,Heimgartner, Heinz
, p. 2385 - 2404 (2007/10/03)
A novel general method for the synthesis of oxindoles, namely the 'azirine/oxindole ring enlargement via amidinium-intermediates' has been established: the reaction of 2H-azirin-3-amines 1 with BF3· OEt2 in THF solution at -78° leads
Diethylphosphine oxide (DEPO): High-yielding and facile preparation of indolones in water
Khan, Tanweer A.,Tripoli, Regis,Crawford, James J.,Martin, Concepcion G.,Murphy, John A.
, p. 2971 - 2974 (2007/10/03)
(Matrix presented) Indolones are prepared in excellent yield at 80°C in water by radical reaction (aryl radical formation, hydrogen atom abstraction, cyclization, and rearomatization) mediated by the reagent diethylphosphine oxide (DEPO). The reaction fea
Tandem Radical Translocation and Homolytic Aromatic Substitution: a Convenient and Efficient Route to Oxindoles
Beckwith, Athelstan L. J.,Storey, John M. D.
, p. 977 - 978 (2007/10/02)
Suitable o-bromo-N-methylanilides are efficiently converted into oxindoles by treatment with tributylstannane at 160 degC via tandem translocation of the initially formed aryl radical and intramolecular homolytic substitution.
Synthesis of 2-Substituted Bicyclopentanes from Bicyclohexan-2-one
Brook, Peter R.,Brophy, Bernard V.
, p. 2509 - 2514 (2007/10/02)
Bicyclohexan-2-one (1) was converted into the 3-diazo derivative (4) wich was ringcontracted thermally to give a variety of amides and esters of bicyclopentane-2-carboxylic acid as exo- and endo-stereoisomers.Conversion of the acids into the corresponding methyl ketones and then Baeyer-Villiger reaction has led to endo- and exo-bicyclopentan-2-yl acetates wich differed markedly in solvolytic reactivity.
