196394-93-1Relevant academic research and scientific papers
Ester-directed orthogonal dual C-H activation and: Ortho aryl C-H alkenylation via distal weak coordination
Agarwal, Vishal,Bakthadoss, Manickam,Reddy, Tadiparthi Thirupathi,Sharada, Duddu S.
supporting information, p. 1406 - 1409 (2022/02/09)
An unprecedented orthogonal cross-coupling between aromatic C(sp2) and aliphatic olefinic C(sp2) carbons of two same molecules via dual C-H bond activation in an intermolecular fashion has been developed using a distal ester-directing group. This new coupling reaction led to the synthesis of the highly functionalized 1,3-diaryl molecular architecture in very good yields and with high chemo- and regioselectivities. In addition, using ester as the distal directing group, ortho C-H olefination of α-methyl aryl acrylates and cinnamic esters with various alkenes has been achieved in very good yields and with a wide range of substrate scope. This journal is
Challenges in the Development of a Thiol-Based Broad-Spectrum Inhibitor for Metallo-β-Lactamases
Büttner, Dominik,Kramer, Jan S.,Klingler, Franca-M.,Wittmann, Sandra K.,Hartmann, Markus R.,Kurz, Christian G.,Kohnh?user, Daniel,Weizel, Lilia,Brüggerhoff, Astrid,Frank, Denia,Steinhilber, Dieter,Wichelhaus, Thomas A.,Pogoryelov, Denys,Proschak, Ewgenij
, p. 360 - 372 (2017/12/18)
Pathogens, expressing metallo-β-lactamases (MBLs), become resistant against most β-lactam antibiotics. Besides the dragging search for new antibiotics, development of MBL inhibitors would be an alternative weapon against resistant bacterial pathogens. Inhibition of resistance enzymes could restore the antibacterial activity of β-lactams. Various approaches to MBL inhibitors are described; among others, the promising motif of a zinc coordinating thiol moiety is very popular. Nevertheless, since the first report of a thiol-based MBL inhibitor (thiomandelic acid) in 2001, no steps in development of thiol based MBL inhibitors were reported that go beyond clinical isolate testing. In this study, we report on the synthesis and biochemical characterization of thiol-based MBL inhibitors and highlight the challenges behind the development of thiol-based compounds, which exhibit good in vitro activity toward a broad spectrum of MBLs, selectivity against human off-targets, and reasonable activity against clinical isolates.
Visible light promoted metal- and photocatalyst-free synthesis of allylarenes
Dossena, Alessandro,Sampaolesi, Susanna,Palmieri, Alessandro,Protti, Stefano,Fagnoni, Maurizio
, p. 10687 - 10692 (2018/03/09)
The metal- and photocatalyst-free synthesis of substituted allylarenes has been carried out under visible light driven conditions. The process was based on the photogeneration of aryl radicals from arylazo sulfones and their ensuing reaction with allyl sulfones. The developed procedure was very efficient when using substrates bearing electron-withdrawing groups, and allowed for the preparation of α-benzyl styrenes and 2-benzyl acrylates in good yields.
Hydrogen Peroxide Promoted Mizoroki-Heck Reactions of Phenyldiazenes with Acrylates, Acrylamides, and Styrenes
Lasch, Roman,Fehler, Stefanie K.,Heinrich, Markus R.
, p. 1586 - 1589 (2016/05/02)
Mizoroki-Heck reactions, which are well-known for aryldiazonium salts and which have recently been described for arylhydrazines, have now been extended to phenyldiazenes. In situ generation of phenyldiazenes from azocarboxylates allowed clean and selective reactions with styrenes, acrylates, and acrylamides using palladium(II) acetate in the presence of silver(I) acetate or hydrogen peroxide as oxidant. Hydrogen peroxide was thereby shown to be a cheap and broadly applicable alternative for the established palladium-silver(I) system.
A versatile approach to noncoded β-hydroxy-α-amino esters and α-amino acids/esters from morita-baylis-hillman adducts
Ullah, Hamid,Ferreira, Andr V.,Bendassolli, Jos A.,Rodrigues, Manoel T.,Formiga, Andr Luiz B.,Coelho, Fernando
, p. 113 - 123 (2015/02/02)
A simple and straightforward approach to the diastereoselective synthesis of noncoded β-hydroxy-α-amino esters from Morita-Baylis-Hillman (MBH) adducts is described. The strategy is based on a one-pot sequence involving an oxidative cleavage of the double bond of silylated Morita-Baylis-Hillman adducts, followed by the reaction with hydroxylamine hydrochloride/pyridine to form oximes. The stereoselective reduction of the oximes with the mixture MoCl5·nH2O/NaBH3CN led to the corresponding anti-β-hydroxy-α-amino esters in four steps in good overall yield and with diastereoselectivity higher than 95%. A slight modification of the synthetic approach has allowed for the racemic synthesis of a set of noncoded α-amino esters/acids and DOPA
High-yielding sequential one-pot synthesis of chiral and achiral α-substituted acrylates via a metal-free reductive coupling reaction
Ramachary, Dhevalapally B.,Venkaiah, Chintalapudi,Reddy, Y. Vijayendar
, p. 5400 - 5406 (2014/07/21)
A general process for the high-yielding synthesis of substituted chiral and achiral α-substituted acrylates was achieved through the sequential one-pot combination of a metal-free reductive coupling reaction followed by an Eschenmoser methylenation. The proline catalyzed reaction of Meldrum's acid, aldehydes and Hantzsch ester followed by methylenation was successful with Eschenmoser's salt in the presence of an alcohol solvent. Herein, we have shown the high-yielding synthesis of privileged building blocks from chiral/achiral α-substituted acrylates and shown them to be very good intermediates in the pharmaceuticals and natural products synthesis. This journal is the Partner Organisations 2014.
Microwave-assisted synthesis of the (E)-α-methylalkenoate framework from multifunctionalized allylic phosphonium salts
Meier, Lidiane,Ferreira, Misael,Sa, Marcus M.
, p. 179 - 186 (2012/07/14)
A convenient and general microwave-assisted method for the synthesis of stereochemically defined α-methylalkenoic acids and esters from allylic phosphonium salts in a basic aqueous medium is described. A selective preparation of acids or esters was dependent on the base (NaOH or NaHCO 3) employed in the reaction and could be achieved with good to excellent yields under mild conditions in the absence of hydrides and reducing agents.
