136167-44-7Relevant academic research and scientific papers
Copper(ii)-catalyzed C-O coupling of aryl bromides with aliphatic diols: Synthesis of ethers, phenols, and benzo-fused cyclic ethers
Liu, Yajun,Park, Se Kyung,Xiao, Yan,Chae, Junghyun
supporting information, p. 4747 - 4753 (2014/06/24)
A highly efficient copper-catalyzed C-O cross-coupling reaction between aryl bromides and aliphatic diols has been developed employing a cheaper, more efficient, and easily removable copper(ii) catalyst. A broad range of aryl bromides were coupled with aliphatic diols of different lengths using 5 mol% CuCl2 and 3 equivalents of K2CO3 in the absence of any other ligands or solvents to afford the corresponding hydroxyalkyl aryl ethers in good to excellent yields. In this newly developed protocol, aliphatic diols have multilateral functions as coupling reactants, ligands, and solvents. The resulting hydroxyalkyl aryl ethers were further readily converted into the corresponding phenols, presenting a valuable alternative way to phenols from aryl bromides. Furthermore, it was demonstrated that they are useful intermediates for more advanced molecules such as benzofurans and benzo-fused cyclic ethers. This journal is
Exploration of l-proline-catalyzed α-aminoxylation of aldehyde to (s)-guaifenesin-related drug molecules
Panchgalle, Sharad P.,Kunte, Sunita S.,Chavan, Subhash P.,Kalkote, Uttam R.
experimental part, p. 1938 - 1946 (2011/06/26)
An efficient enantioselective synthesis of (S)-guaifenesin with >99% ee using L-proline-catalyzed α-aminoxylation of aldehyde as key step is described and explored for asymmetric syntheses of (S)-moprolol and (R)-methocarbamol.
Multistep solution-phase parallel synthesis of spiperone analogues
Hansen, Henrik C.,Olsson, Roger,Croston, Glenn,Andersson, Carl-Magnus
, p. 2435 - 2439 (2007/10/03)
A flexible, multistep parallel synthesis of spiperone analogues is described. A library of 4-substituted piperidines, assembled utilizing reductive amination and acylation protocols, was alkylated either homogeneously or heterogeneously, exploiting a product release only concept, to afford an oxa-series of spiperone analogues. Screening of the products at 5-HT2 and D2 receptors revealed 5-HT(2A) antagonists with improved selectivity compared to spiperone and AMI-193. (C) 2000 Published by Elsevier Science Ltd.
Cyclotriveratrylene models for proteins: 3:1 subsite differentiation and modulation of the redox potential
Strijdonck, Gino P. F. van,Haare, John A. E. H. van,Hoenen, Paulus J.M.,Schoor, Roger C. G. M. van den,Feiters, Martinus C.,et al.
, p. 449 - 462 (2007/10/03)
The potential of cyclotriveratrylene (ctv) (2,3,7,8,12,13-hexamethoxy-10,15-dihydro-5H-tribenzocyclo-nonene) trithiols as ligands that can easily be functionalised and show subsite differentiation in their complexes with clusters has been explored.The cluster complexes of tris(2-sulfanylethoxy)- and tris(3-sulfanyl-methylbenzyloxy)-functionalised ctvs have been studied by core-extrusion experiments, spectroscopy and electrochemical techniques.With 2- as starting material a cluster complex was obtained in which the unique Fe and its co-ordinating Cl was turned into the cavity and show no reactivity.Starting with the more bulky t)4>2- the unique iron points outwards and is susceptible to substitution reactions.The effects of hydrogen bonding and electron density on the redox potential of the cluster complex have been investigated.The redox potential becomes more negative when the length of the spacer between the ctv and cluster core is increased, which is explained by the longer distance between the cluster and the electron-withdrawing phenoxy moiety of the ctv.The synthesis of ctv derivatives with one thiol and one alcohol functionality per phenyl unit, and comparison with corresponding derivatives where hydrogen bonding is not possible, showed that no significant differences were found.The effects of a substituent in an aromatic amide group that could hydrogen bond to the co-ordinated thiol were investigated.A weak effect, in the direction expected, was found upon substitution of methyl for H.
Aryl and aryloxyalkyl sulfamate esters useful as anticonvulsants
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, (2008/06/13)
Herein disclosed is a method of treating convulsions with a pharmaceutical composition containing a compound of the formula: where A is an aryl, arylalkyl, or aryloxyalkyl group and is substituted on 1 or more carbon atoms with a sulfamate group (--OSO2 NR1 R2) wherein R1 and R2, same or different, are hydrogen or loweralkyl wherein p is 0 or 1 and is the number of untreated hydroxyl groups and z is 1 or 2 and is the number of --OS(O2)NR1 R2 groups. Aryl is selected from phenyl, substituted phenyl, pyridinyl, naphthyl, quinolinyl, and the like. Phenyl substituents are selected from hydrogen, halo, hydroxy, phenyl, phenoxy, benzoyl, loweralkyl, loweralkoxy, carboxy, amino, loweralkylamino, diloweralkylamino, acetamido, cyano, nitro, loweralkoxycarboyl, aminosulfonyl, imidazolyl, triazolyl, and the like. Novel compounds not previously disclosed are also described.
