22616-15-5Relevant articles and documents
Bifunctional agents for reperfusion arrhythmias: Novel hybrid vitamin E/class I antiarrhythmics
Koufaki, Maria,Calogeropoulou, Theodora,Rekka, Eleni,Chryselis, Michael,Papazafiri, Panagiota,Gaitanaki, Catherine,Makriyannis, Alexandros
, p. 5209 - 5219 (2003)
We have synthesized a series of hybrid compounds combining the pharmacophoric redox moieties of vitamin E and key features responsible for the antiarrhythmic properties of the class I antiarrhythmics procainamide and lidocaine. Procainamide analogue (2a) and lidocaine analogues (14a) and (14b) are very strong inhibitors of lipid peroxidation. All analogues tested at 100 or 30 μM enhanced the post ischemic recovery without inducing ventricular fibrillations while there was no evidence in our experiments for drug-induced pro-arrhythmia. In addition, they induced a widening of the QRS intervals. Our data suggest that the efficacy of the new compounds in preventing reperfusion arrhythmias could be attributed to their combined effects involving inhibition of free radical mediated damage coupled with antiarrhythmic properties.
Photochemical Organocatalytic Regio- and Enantioselective Conjugate Addition of Allyl Groups to Enals
Berger, Martin,Carboni, Davide,Melchiorre, Paolo
supporting information, p. 26373 - 26377 (2021/11/16)
We report the first catalytic enantioselective conjugate addition of allyl groups to α,β-unsaturated aldehydes. The chemistry exploits the visible-light-excitation of chiral iminium ions to activate allyl silanes towards the formation of allylic radicals, which are then intercepted stereoselectively. The underlying radical mechanism of this process overcomes the poor regio- and chemoselectivity that traditionally affects the conjugate allylation of enals proceeding via polar pathways. We also demonstrate how this organocatalytic strategy could selectively install a valuable prenyl fragment at the β-carbon of enals.
Allylation of nitrosobenzene with pinacol allylboronates. A regioselective complement to peroxide oxidation
Kyne, Robert E.,Ryan, Michael C.,Kliman, Laura T.,Morken, James P.
supporting information; experimental part, p. 3796 - 3799 (2010/10/21)
Addition of nitrosobenzene to pinacol allylboronates leads to oxidation of the organoboron with concomitant rearrangement of the substrate alkene. This reaction appears to proceed by allylboration of the nitroso group in analogy to carbonyl and imine allylation reactions. Remarkably, the N-O bond is cleaved during the reaction such that simple alcohols are the final reaction product.
A Novel Synthesis of Homologated Allylic Alcohols Using Dimethylsulphonium Methylide
Harnett, J. J.,Alcaraz, L.,Mioskowski, C.,Martel, J. P.,Gall, T. Le,et al.
, p. 2009 - 2012 (2007/10/02)
The reaction of excess dimethylsulphonium methylide with various aliphatic and aromatic ketones leads exclusively to homologated allylic alcohols in good yields.
EFFECT OF THE STRUCTURE OF SUBSTITUTED PROPARGYL AND ALLYL ALCOHOLS ON THE RATE OF THEIR LIQUID PHASE HYDROGENATION ON A Pd-Ru ALLOY MEMBRANE CATALYST
Karavanov, A. N.,Gryaznov, V. M.
, p. 1593 - 1596 (2007/10/02)
The rates of hydrogenation of substituted propargyl and allyl alcohols in the liquid phase on a Pd-Ru alloy membrane catalyst are described by a two-parameter Taft equation which takes into account the inductive and steric effects of the substituents.The values of the parameters at 363 K with H2 at atmospheric pressure are: ρ* = -0.20, δ = 0.10 and ρ+ = -1.1, δ = 1.3 respectively.
ISOMERIZATION OF ALLYLIC ALCOHOLS CATALYZED BY VANADIUM OR MOLYBDENUM COMPLEXES.
Matsubara,Okazoe,Oshima,Takai,Nozaki
, p. 844 - 849 (2007/10/02)
Isomerization of primary allylic alcohols proceeds in dichloromethane at 25 degree C in the presence of the catalyst prepared in situ from VO(acac)//2 or MoO//2(acac)//2, and Me//3SiOOSiMe//3 to give tertiary isomers in good yields. The catalysts are also effective for the rearrangements of sec. yields tert. allylic alcohols. The isomerization of an allenyl allylic alcohol, 6-methyl-1,2,5-heptatrien-4-ol, gives either (E)-2-methyl-3,5,6-heptarien-2-ol or (E)-6-methyl-3,5-heptadien-2-one selectively depending on the reaction conditions.
ISOMERIZATION OF PRIMARY ALLYLIC ALCOHOLS TO TERTIARY ONES BY MEANS OF Me3SiOOSiMe3-VO(acac)2 CATALYST
Matsubara, Seijiro,Takai, Kazuhiko,Nozaki, Hitosi
, p. 3741 - 3744 (2007/10/02)
The title rearrangement proceeds in dichloromethane at 25 oC in the presence of the catalyst prepared in situ to give tertiary isomers in good yields.Other rearrangements of sec. -> tert. or sec. -> sec. have been examined.
