75804-36-3Relevant academic research and scientific papers
One-pot facile synthesis of substituted isoindolinones via an Ugi four-component condensation/Diels-Alder cycloaddition/deselenization- aromatization sequence
Huang, Xian,Xu, Jianfeng
supporting information; experimental part, p. 8859 - 8861 (2010/03/01)
(Chemical Equation Presented) A versatile one-pot synthesis of substituted isoindolinones from 2-furaldehydes, amines, 2-(phenylselanyl)-acrylic acids, and isocyanides is described. The tandem process involves the Ugi four-component condensation, intramol
Synthesis of oxa-bridged analogues of farnesyltransferase inhibitor RPR 115135
Martin,Mailliet,Maddaluno
, p. 3797 - 3805 (2007/10/03)
Two synthetic routes to new oxygen-bridged analogues of farnesyltransferase inhibitors are described that follow either a [3 + 2]/[4 + 2] or a [4 + 2]/[3 + 2] sequence of reactions. The first approach has been achieved by reacting the in situ generated phenylisobenzofuran (PIBF) 4 with pyrroline 5a and has led stereoselectively to racemic 18, which was transformed in a few steps into the target molecule 2. The second pathway relies on a key intermediate 6, obtained either by condensation of PIBF with methyl acrylate, followed by a deprotonation/selenation and an oxidation/elimination sequence, or by cycloaddition between PIBF and α-phenylselenoacrylate 11, followed by the same oxidation/elimination sequence. The reaction of 6 with amino dipole 7 gives diastereoselective access to pyrrolidine 25, a precursor of the second target 3, an epimer of 2.
A diastereoselective switch in the access to isobenzofuran-derived α-selenoesters
Martin, Celine,Mailliet, Patrick,Maddaluno, Jacques
, p. 923 - 925 (2007/10/03)
(equation presented) The cycloaddition of 1-phenylisobenzofuran (PIBF) with methyl acrylate yields, in a moderate endo/exo ratio, the expected oxa-bridged adduct, which can be deprotonated and condensed on diphenyl diselenide to provide, in a stereoconver
A radical cyclization route to pyrrolidines based on conjugate addition to electron deficient phenylselenenylalkenes
Berlin, Stefan,Engman, Lars
, p. 3701 - 3704 (2007/10/03)
α-Phenylselenenyl-α,β-unsaturated esters, amides, ketones, nitriles and sulfones were prepared by zinc chloride promoted chloroselenation/dehydrochlorination of the corresponding α,β-unsaturated compounds. After Michael addition of allyl or propargylamine and triethylborane initiated reductive radical cyclization in the presence of tris(trimethylsilyl)silane, pyrrolidine and dihydropyrrole derivatives, respectively, were obtained. (C) 2000 Elsevier Science Ltd.
CAPTODATIVE SUBSTITUENT EFFECTS XXI. SYNTHESIS OF SELENENYLATED CAPTODATIVE OLEFINS VIA SELENENYL HALIDE ADDITION TO OLEFINS BEARING ELECTRON-WITHDRAWING SUBSTITUENTS
Piettre, S.,Janousek, Z.,Merenyi, R.,Viehe, H. G.
, p. 2527 - 2544 (2007/10/02)
Addition of methane- and benzeneselenenyl bromide or chloride and benzene sulfenyl chloride to carbon-carbon double bonds substituted by electron-withdrawing groups is achieved in solvents of different polarity.Two regioisomeric adducts 6 and 7 or 8 and 9 are generally formed, which can be interconverted by equilibration in refluxing acetonitrile.It is of mechanistic interest that the regioisomers may also derive from selenenyltrihalide adducts.In comparison to acrylic esters, the propiolic ester reacts more slowly, producing mainly the α-selenenyl adduct.Dehydrohalogenation of adducts provides a general and valuable method for the preparation of olefins carrying methyl or phenylselenyl groups in α-position to electron-withdrawing substituents.
CAPTO-DATIVE SUBSTITUENT EFFECTS XIII. C4-BRIDGED RADICAL DIMERISATION WITH α-PHENYLSELENOACRYLIC ACID DERIVATIVES
Janousek, Z.,Piettre, S.,Gorissen-Hervens, F.,Viehe, H.G.
, p. 197 - 202 (2007/10/02)
Several capto-dative olefins containing the phenylselenenyl group have been obtained via selenenyl halide addition to acrylic derivatives followed by halide elimination.Some of the olefins efficiently trap the radicals formed from azobisisobutyronitrile (
