54168-07-9Relevant academic research and scientific papers
Unexpected results of a SNAr-reaction. A novel synthetic approach to 1-arylthio-2-naphthols
Grombein, Cornelia M.,Hu, Qingzhong,Heim, Ralf,Huch, Volker,Hartmann, Rolf W.
, p. 6615 - 6618 (2013)
1-(Phenylthio)-3-(pyridin-3-yl)-2-naphthol was obtained as an unexpected result of a nucleophilic aromatic substitution reaction of 3-(pyridine-3-yl) naphthalene-2-yl trifluoromethanesulfonate with thiophenol. This observation led to the discovery of an e
Remote meta-C–H Cyanation of Arenes Enabled by a Pyrimidine-Based Auxiliary
Bag, Sukdev,Jayarajan, Ramasamy,Dutta, Uttam,Chowdhury, Rajdip,Mondal, Rahul,Maiti, Debabrata
supporting information, p. 12538 - 12542 (2017/09/12)
An easily removable pyrimidine-based auxiliary has been employed for the remote meta-C?H cyanation of arenes. The scope of this Pd-catalyzed cyanation reaction using copper(I) cyanide as the cyanating agent was demonstrated with benzylsilanes, benzylsulfonates, benzylphophonates, phenethylsulfonates, and phenethyl ether derivatives. The method was utilized for the synthesis of pharmaceutically valuable precursors.
Template-Assisted meta-C?H Alkylation and Alkenylation of Arenes
Bag, Sukdev,Jayarajan, Ramasamy,Mondal, Rahul,Maiti, Debabrata
supporting information, p. 3182 - 3186 (2017/03/17)
To expand the scope of meta-functionalization, a pyrimidine-based template effective for the formation of β-aryl aldehydes and ketones, using allyl alcohols, by meta-C?H activation of benzylsulfonyl esters is described. In addition, α,β-unsaturated aldehydes were generated by in situ olefination and deprotection of allyl benzyl ethers. These new functionalizations at the meta-position of an arene have also been successfully implemented in benzylphosphonate, phenethyl carbonyl, and phenethylsulfonyl ester scaffolds. Key to these successful new functionalizations is the creation of an electropositive palladium center by accepting the electron cloud from the metal to the energetically low-lying π-orbitals of pyrimidine ring, and it favors coordination of allyl alcohol to the metal center.
Recent developments in the chemistry of heteroaromatic N -oxides
Wang, Youliang,Zhang, Liming
, (2015/02/19)
Selected developments in the chemistry of heteroaromatic N-oxides since 2001 are presented in this review. The use of these N-oxides, both in late-transition-metal-catalyzed oxidations of carbon-carbon triple bonds and in regioselective C-H functionalizations of the heteroarene, are contemporary topics of interest and the focus of the discussion. 1 Introduction 2 Synthesis of Heteroaromatic N-Oxides 2.1 Direct Oxidation of Hindered Heteroarenes 2.2 Through Construction of Heteroaromatic Rings 3 Heteroaromatic N-Oxides as Oxidants 3.1 Alkyne Oxidation 3.2 Allene Oxidation 3.3 Carbene Oxidation 4 Heteroaromatic N-Oxides as Substrates 4.1 Deoxygenative ortho-C-H Functionalization with Prior Activation 4.2 Deoxygenative ortho-C-H Functionalization with Nonstabilized Carbanions 4.3 Nondeoxygenative C-H Functionalization 4.3.1 ortho-C-H Functionalization 4.3.2 N-Oxide Directed ortho-Alkyl C-H Functionalization 4.3.3 N-Oxide Directed Remote C-H Functionalization 4.4 1,3-Dipolar Cycloaddition 5 Conclusion and Outlook.
N-ACYLHYDRAZONE DERIVATIVES FOR SELECTIVE T CELL INHIBITOR AND ANTI-LYMPHOID MALIGNANCY DRUG
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Page/Page column 74, (2014/03/25)
The present invention relates to novel N-acylhydrazone derivatives, and more particularly to novel N-acylhydrazone derivatives having selective T cell inhibitory activity and/or anti-lymphoid malignancy activity, stereoisomers thereof, pharmaceutically acceptable salts thereof, the use thereof for preparing pharmaceutical compositions, pharmaceutical compositions containing the same, treatment methods using the compositions, and methods for preparing the novel N-acylhydrazone derivatives.
DERIVATIVES OF 6-SUBSTITUTED TRIAZOLOPYRIDAZINES AS REV-ERB AGONISTS
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Page/Page column 43; 58, (2013/04/13)
The present invention provides novel 6-substituted [1,2,4]triazolo[4,3-b]pyridazines that are agonists of Rev-Erb. These compounds, and pharmaceutical compositions comprising the same, are suitable means for treating any disease wherein the activation of Rev-Erb has therapeutic effects, for instance in inflammatory and circadian rhythm-related disorders or cardiometabolic diseases.
Regioselective synthesis of 2-(2-hydroxyaryl)pyridines from the reactions of benzynes with pyridine N-oxides
Shaibu, Balagopal S.,Kawade, Rahul Kisan,Liu, Rai-Shung
, p. 6834 - 6839 (2012/11/07)
By modifying the conditions from those in Larock's reported synthesis of 3-(2-hydroxyaryl)pyridines from benzynes, and pyridine N-oxides, we altered the regioselectivity of the reaction toward an efficient synthesis of 2-substituted pyridines. The presenc
NOVEL PHENOL COMPOUNDS AND (CO)POLYMERS THEREOF
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Page/Page column 10, (2009/09/05)
The present invention relates to A phenol compound according to Formula (I): wherein: R1 is selected from the group consisting of, optionally substituted, 2-pyridyl, 3-pyridiyl and 4-pyridyl groups, wherein R1 is at position 2 or 3 o
Regioselective synthesis of 3-(2-hydroxyaryl)pyridines via arynes and pyridine N-oxides
Raminelli, Cristiano,Liu, Zhijian,Larock, Richard C.
, p. 4689 - 4691 (2007/10/03)
A variety of substituted 3-(2-hydroxyphenyl)pyridines have been prepared regioselectively by a transition-metal-free, mild, one-step route, which involves the reaction of pyridine N-oxides with silylaryl triflates in the presence of CsF in acetonitrile at
Radical dearomatization of arenes and heteroarenes
Crich, David,Patel, Mitesh
, p. 7824 - 7837 (2007/10/03)
The stannane-mediated benzeneselenol-catalyzed addition of aryl iodides to a range of arenes and aromatic hetereocycles has been studied. With furan, thiophene, and several carbocyclic arenes, the addition takes place with quenching of the adduct radical by the catalytic selenol leading to moderate yields of aryl-dihydroarenes. With nitrogen heterocycles, on the other hand, it was not possible to suppress aromatization of the adduct radical and fully aromatized products were isolated. Aryl iodides bearing hydrogen bond donating groups in the ortho-position add to nitrogen heterocycles with high selectivity ortho- to the nitrogen, affording a simple one-step synthesis of potential chelating ligands. While 2-iodophenol is an excellent aryl radical source in these reactions, the homologous 1-iodo-2-naphthol fails owing to its reaction with diphenyl diselenide, which gives 1-phenylseleno-2-naphthol in high yield.
