122101-00-2Relevant academic research and scientific papers
Silver-promoted, palladium-catalyzed direct arylation of cyclopropanes: Facile access to spiro 3,3′-cyclopropyl oxindoles
Ladd, Carolyn L.,Sustac Roman, Daniela,Charette, André B.
, p. 1350 - 1353 (2013/05/09)
The Pd-catalyzed, Ag(I)-mediated intramolecular direct arylation of cyclopropane C-H bonds is described. Various spiro 3,3′-cyclopropyl oxindoles can be obtained in good to excellent yields from easily accessible 2-bromoanilides. The kinetic isotope effect was determined and epimerization studies were conducted, suggesting that the formation of a putative Pd-enolate is not operative and that the reaction proceeds via a C-H arylation pathway.
Tandem Horner-Wadsworth-Emmons/Heck procedures for the preparation of 3-alkenyl-oxindoles: The synthesis of Semaxanib and GW441756
Lubkoll, Jana,Millemaggi, Alessia,Perry, Alexis,Taylor, Richard J.K.
experimental part, p. 6606 - 6612 (2010/10/19)
A tandem sequence involving Horner-Wadsworth-Emmons (HWE) olefination followed by a palladium-catalysed intramolecular Heck reaction has been developed to provide rapid access to 3-alkenyl-oxindoles from α-halo-anilides. This one-pot microwave accelerated process proceeds with catalytic palladium(II) acetate or tetrakis(triphenylphosphine)palladium, and has been used to prepare a range of adducts derived from aromatic, heteroaromatic and aliphatic aldehydes. The procedures can be used to prepare N-unprotected oxindoles directly and the applicability of the process has been established by carrying out one-pot syntheses of Semaxanib, an angiogenesis signalling inhibitor, and GW441756, an aza-oxindole Trk A inhibitor.
SYNTHESIS OF OXINDOLES BY RADICAL CYCLISATION
Bowman, W. Russell,Heaney, Harry,Jordan, Benjamin M.
, p. 6657 - 6660 (2007/10/02)
Oxindoles are readily synthesised by intramolecular addition of aryl radicals to the α-position of α,β-unsaturated N-alkylamides.
