92199-93-4Relevant academic research and scientific papers
Palladium-catalyzed decarboxylative coupling of potassium nitrophenyl acetates with aryl halides
Shang, Rui,Huang, Zheng,Chu, Ling,Fu, Yao,Liu, Lei
supporting information; experimental part, p. 4240 - 4243 (2011/10/09)
A palladium-catalyzed decarboxylative cross-coupling of potassium 2- and 4-nitrophenyl acetates with aryl chlorides and bromides has been developed. Because the nitro group can be readily converted to many other functional groups, the new reaction provides a useful method for the preparation of diverse 1,1-diaryl methanes and their derivatives.
Quinolone carboxylic acids as a novel monoketo acid class of human immunodeficiency virus type 1 integrase inhibitors
Sato, Motohide,Kawakami, Hiroshi,Motomura, Takahisa,Aramaki, Hisateru,Matsuda, Takashi,Yamashita, Masaki,Ito, Yoshiharu,Matsuzaki, Yuji,Yamataka, Kazunobu,Ikeda, Satoru,Shinkai, Hisashi
experimental part, p. 4869 - 4882 (2010/03/02)
Human immunodeficiency virus type 1 (HIV-1) integrase is a crucial target for antiretroviral drugs, and several keto - enol acid class (often referred to as diketo acid class) inhibitors have clinically exhibited-marked antiretroviral activity. Here, we show the synthesis and the detailed structure - activity relationship of the quinolone carboxylic acids as a novel monoketo acid class of integrase inhibitors. 6-(3-Chloro-2-fluorobenzyl)-1-((2S)-1-hydroxy-3,3- dimethylbutan-2-yl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 51, which showed an IC50 of 5.8 nMin the strand transfer assay and an ED50 of 0.6 nMin the antiviral assay, and 6-(3-chloro-2-fluorobenzyl) -1-((2S)-1-hydroxy-3-methylbutan-2-yl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3- carboxylic acid 49, which had an IC50 of 7.2 nMand an ED50 of 0.9 nM, were the most potent compounds in this class. The monoketo acid 49 was much more potent at inhibiting integrasecatalyzed strand transfer processes than 3′-processing reactions, as is the case with the keto - enol acids. Elvitegravir 49 was chosen as a candidate for further studies and is currently in phase 3 clinical trials.
Suzuki cross-coupling reaction of benzylic halides with arylboronic acids in the presence of a tetraphosphine/palladium catalyst
Chahen, Ludovic,Doucet, Henri,Santelli, Maurice
, p. 1668 - 1672 (2007/10/03)
The cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane-[PdCl(C3H5)]2 system catalyses efficiently the Suzuki cross-coupling reaction of benzylic halides with arylboronic acids. A wide variety of benzylic bromides or chlorides and functionalised arylboronic acids lead selectively to the corresponding diarylmethane adducts in good yields. Furthermore, this catalyst can be used at low loading in many cases.
Environmentally friendly arylmethylation of aromatics with benzyl halides using envirocat EPZ10 as the catalyst
Bandgar, Babasaheb P.,Kasture, Suhas P.
, p. 913 - 915 (2007/10/03)
The Friedel-Crafts arylmethylation of aromatics with benzyl halides or bis-(bromomethyl)-benzene in the presence of Envirocat EPZ10 affords selectively para-arylmethylated products in good yields. Isolation of pure products involving an eco-friendly procedure and recyclability of the catalyst are important features of this method.
Palladium-catalyzed coupling reaction of 4-alkylnitrobenzenes with aryl bromides at their benzylic position
Inoh, Jun-Ichi,Satoh, Tetsuya,Pivsa-Art, Sommai,Miura, Masahiro,Nomura, Masakatsu
, p. 4673 - 4676 (2007/10/03)
4-Alkylnitrobenzenes effectively undergo coupling with aryl bromides at their benzylic position in the presence of a palladium catalyst and a base to give the corresponding mono- and/or di-arylated products in good yields.
Electrophilic aromatic substitution. 12. Kinectic studies of the TiCl4-catalyzed reactions of benzyl chloride, p-xylyl chloride, and p-nitrobenzyl chlordie with benzene and anisole in nitromehtane and dichloromethabe
DeHaan, Franklin P.,Chan, Wai H.,Chang, Jeffrey,Cheng, Terry B.,Chiriboga, Douglas A.,Irving, Mark M.,Kaufman, Craig R.,Kim, Gia Y.,Kumar, Amit,Na, Jim,Nguyen, Tien T.,Tim Nguyen,Patel, Bimal R.,Sarin, Neal P.,Tidwell, Jeffrey H.
, p. 356 - 363 (2007/10/02)
Through the use of vacuum line techniques, noncompetitive and competitive kinetic data have been obtained for the TiCl4-catalyzed reactions of benzyl chloride and p-methyl- and p-nitrobenzyl chloride with anisole and with benzene in solvents ni
Selective Thyromimetics. Cardiac-Sparing Thyroid Hormone Analogues Containing 3'-Arylmethyl Substituents
Leeson, Paul D.,Emmett, John C.,Shah, Virendra P.,Showell, Graham A.,Novelli, Ricardo,et al.
, p. 320 - 336 (2007/10/02)
Introduction of specific arylmethyl groups at the 3'-position of the thyroid hormone 3,3',5-triiodo-L-thyronine (T3), and its known hormonally active derivatives, gives liver-selective, cardiac-sparing thyromimetics, with potential utility as plasma cholesterol lowering agents.Selectivity-conferring 3'-substituents include substituted benzyl, e.g. p-hydroxybenzyl, and heterocyclic methyl, e.g. 2-oxo-1,2-dihydropyrid-5-ylmethyl and 6-oxo-1,6-dihydropyridazin-3-ylmethyl.Correlations between in vivo and in vitro receptor binding affinities show that liver/heart selectivity does not depend on receptor recognition but on penetration or access to receptors in vivo.QSAR studies of the binding data of a series of 20 3'-arylmethyl T3 analogues show that electronegative groups at the para position increase both receptor binding and selectivity in vivo.However, increasing 3'-arylmethyl hydrophobicity increases receptor binding but reduces selectivity.Substitution at ortho and meta positions reduces both binding and selectivity.Replacement of the 3,5-iodo groups by halogen or methyl maintains selectivity, with 3,5-dibromo analogues in particular having increased potency combined with oral bioavailability.Diphenyl thioether derivatives also have improved potency but are less orally active.At the 1-position, the D enantiomer retains selectivity, but removal of the α-amino group to give a propionic acid results in loss of selective thyromimetic activity.
4-NITROBENZYLATION OF PHENOL AND ANISOLE IN THE PRESENCE OF SMALL AMOUNTS OF FERRIC CHLORIDE
Tadzhimukhamedov, Kh. S.,Abdurasuleva, A. R.,Akhmedov, K. N.
, p. 944 - 946 (2007/10/02)
Unlike other substituted benzylchlorides, 4-nitrobenzyl chloride enters into reaction with phenol and anisole in the presence of 1E-2 - 1E-3 mole of ferric chloride.The yields of the 4-nitrobenzylphenols (anisoles) amount to 64-80percent.It was shown that
FRIEDEL-CRAFTS ALKYLATION OF ANISOLE AND ITS COMPARISON WITH TOLUENE. PREDOMINANT ORTHO-PARA SUBSTITUTION UNDER KINETIC CONDITIONS AND THE EFFECT OF THERMODYNAMIC ISOMERIZATIONS
Olah, George A.,Olah, Judith A.,Ohyama, Toshiyuki
, p. 5284 - 5290 (2007/10/02)
The AlCl3 and BF3, as well as 65percent HPF6, catalyzed Friedel-Crafts alkylation of anisole with alkyl halides and alkohols was investigated.The alkylation of anisole with lower catalyst concentrations under mild conditions shows predominant ortho/para directing effect generally with a ratio of c.a. 2:1, with the amount of meta isomer uniformly less than 3percent.With "swamping" catalyst conditions the amount of meta substitution in methylation and ethylation can substantially increase.The isomer distribution in tert-butylation changes with time due to rapid ortho-para interconversion.Consequently, the AlCl3-catalyzed isomerization of isomeric alkylanisoles was also studied.In case of tert-butylanisoles, the ortho isomer shows relatively rapid conversion into para followed by much slower isomerization to meta.The para and meta isomers show isomerization to meta-para mixtures.Isomerization of ethyl-, isopropyl-, and benzylanisoles is generally slow whereas methylanisoles do not isomerize.Comparing results of the alkylation of anisole with toluene leads to the conclusion that the latter are readily affected by concurrent (and in some cases consecutive) isomerization.As the barrier for isomerization in the benzenium ion intermediates of the alkylations is higher in the case of CH3O- than CH3-substituted systems, anisole tends to give the kinetically controlled ortho-para alkylation products and the amount of meta isomer is low.Study of alkylation of 3,5-di- and 2,4,6-trideuterated toluene and anisole and comparing retained deuterium contents with isomer distributions shows that alkylated product formation in case of toluene, but not of anisole, is proceeded by intramolecular, 1,2-alkyl, and hydrogen-deuterium shifting resulting also in increased meta substitution.This effect is most predominant in methylation and ethylation where the alkyl shifts are intramolecular but not in tert-butylation and benzylation, where alkyl transfer is intermolecular.Isopropylation is intermediate in nature.No simple selectivity-reactivity relationship is indicated in the studied alkylation reactions.As shown in benzylations with increasingly electron-donating and -withdrawing substituted benzyl chlorides overall rate (i.e., substrate selectivity) and isomer distributions (i.e., regioselectivity) are not determined in the same step as significantly decreased substrate selectivity is not accompanied by loss of positional selectivity.Previously reported alkylations showing high degree of meta substitution therefore, must have been affected by thermodynamically controlled rearrangement processes, including intramolecular alkyl and hydrogen shifts in the arenium ion intermediates of the alkylation reactions.These are to be differentiated from possible subsequent product isomerizations.Under predominantly kinetic conditions anisole as well as toluene are substantially ortho-para directing in alkylations, as in other electrophilic aromatic substitutions.
