7596-36-3Relevant academic research and scientific papers
Cyclization of Active Methylene Isocyanides with α-Oxodithioesters Induced by Base: An Expedient Synthesis of 4-Methylthio/Ethoxycarbonyl-5-acylthiazoles
Anil, Seegehalli M.,Kiran, Kuppalli R.,Rajeev, Narasimhamurthy,Rangappa, Kanchugarakoppal S.,Sadashiva, Maralinganadoddi P.,Swaroop, Toreshettahally R.
, p. 1444 - 1450 (2020/04/27)
Cyclization of tosylmethyl isocyanide with α-oxodithioesters in the presence of KOH is reported for the synthesis of 4-methylthio-5-acylthiazoles. Similarly, ethyl isocyanoacetate underwent cyclization with α-oxodithioesters to form 4-ethoxycarbonyl-5-acy
Optimization of Catalyst Structure for Asymmetric Propargylation of Aldehydes with Allenyltrichlorosilane
Vaganov, Vladimir Yu.,Fukazawa, Yasuaki,Kondratyev, Nikolay S.,Shipilovskikh, Sergei A.,Wheeler, Steven E.,Rubtsov, Aleksandr E.,Malkov, Andrei V.
, p. 5467 - 5474 (2020/10/19)
The design of catalysts for asymmetric propargylations remains a challenging task, with only a handful of methods providing access to enantioenriched homopropargylic alcohols. In this work, guided by previously reported computational predictions, a set of
Stereoselective Synthesis of Atropisomeric Bipyridine N,N′-Dioxides by Oxidative Coupling
Fukazawa, Yasuaki,Vaganov, Vladimir Yu.,Shipilovskikh, Sergei A.,Rubtsov, Aleksandr E.,Malkov, Andrei V.
supporting information, p. 4798 - 4802 (2019/06/17)
Bipyridine N,N′-dioxide is a structural fragment found in many bioactive compounds. Furthermore, chiral analogues secured their place as powerful Lewis base catalysts. The scope of the existing methods for the synthesis of atropisomeric bipyridine N,N′-di
Acid-Catalyzed Condensation of o-Phenylenediammines and o-Aminophenols with α-Oxodithioesters: A Divergent and Regio? selective Synthesis of 2-Methylthio-3-Aryl/Heteroarylquinoxalines and 2-Acylbenzoxazoles
Anil, Seegehally M,Kiran, Kuppalli R,Rangappa, Kanchugarakoppal S,Sadashiva, Maralinganadoddi P,Shruthi, Jeegundipattana B,Sukrutha, Kodipura P,Swaroop, Toreshettahally R
, p. 4205 - 4214 (2019/11/14)
o-Phenylenediammines and o-Aminophenols were reacted with α-oxodithioesters in a highly regioselective fashion to give 2-methylthio-3-Aryl/heteroarylquinoxalines and 2-Acylbenzoxazoles in 55-94percent and 45-86percent, respectively, in the presence of p-T
Kr?hnke pyridines: Rapid and facile access to Mcl-1 inhibitors
Conlon, Ivie L.,Van Eker, Daniel,Abdelmalak, Sameh,Murphy, William A.,Bashir, Hassan,Sun, Michael,Chauhan, Jay,Varney, Kristen M.,Godoy-Ruiz, Raquel,Wilder, Paul T.,Fletcher, Steven
supporting information, p. 1949 - 1953 (2018/05/04)
The tumorigenic activity of upregulated Mcl-1 is manifested by binding the BH3 α-helical death domains of opposing Bcl-2 family members, neutralizing them and preventing apoptosis. Accordingly, the development of Mcl-1 inhibitors largely focuses on synthe
Mechanistic dichotomy in the asymmetric allylation of aldehydes with allyltrichlorosilanes catalyzed by chiral pyridine N-oxides
Malkov, Andrei V.,Stoncius, Sigitas,Bell, Mark,Castelluzzo, Fabiomassimo,Ramirez-Lopez, Pedro,Biedermannova, Lada,Langer, Vratislav,Rulisek, Lubomir,Kocovsky, Pavel
, p. 9167 - 9185 (2013/07/26)
Detailed kinetic and computational investigation of the enantio- and diastereoselective allylation of aldehydes 1 with allyltrichlorosilanes 5, employing the pyridine N-oxides METHOX (9) and QUINOX (10) as chiral organocatalysts, indicate that the reaction can proceed through a dissociative (cationic) or associative (neutral) mechanism: METHOX apparently favors a pentacoordinate cationic transition state, while the less sterically demanding QUINOX is likely to operate via a hexacoordinate neutral complex. In both pathways, only one molecule of the catalyst is involved in the rate- and selectivity-determining step, which is supported by both experimental and computational data. Copyright
Coupling of azomethine ylides with nitrilium derivatives of closo-decaborate clusters: A synthetic and theoretical study
Mindich, Aleksey L.,Bokach, Nadezhda A.,Kuznetsov, Maxim L.,Haukka, Matti,Zhdanov, Andrey P.,Zhizhin, Konstantin Yu.,Miltsov, Serguei A.,Kuznetsov, Nikolay T.,Kukushkin, Vadim Yu.
, p. 1075 - 1086 (2013/03/13)
The azomethine ylides p-R3C5H4N+CHCOC 6H4R2-p (3a: R3=H, R2=H, X=Br; 3b: R3=H, R2=Me, X=I; 3c: R3=H, R2=OMe, X=I; 3d: R3=H, R2=F, X=I; 3e: R3=Me, R2=Me, X=Br) react with the nitrile functio
Direct conversion of aromatic ketones to arenecarboxylic esters via carbon-carbon bond-cleavage reactions
Yin, Guodong,Gao, Meng,Wang, Zihua,Wu, Yandong,Wu, Anxin
experimental part, p. 369 - 372 (2009/04/07)
Aromatic methyl ketones, ss-keto esters, and trifluoromethyl-l,3- diketones can be directly converted to arene-carboxylic esters via carbon-carbon bond cleavage of pyridinium iodide intermediates in the presence of copper(II) oxide, iodine, pyridine, and potassium carbonate in alcoholic media. The advantages of the present method in terms of good yields, mild reaction conditions, and inexpensive reagents should make this protocol a valuable alternative to the existing methods.
Facile synthesis of cyclometalated ruthenium complexes with substituted phenylpyridines
Sasaki, Isabelle,Vendier, Laure,Sournia-Saquet, Alix,Lacroix, Pascal G.
, p. 3294 - 3302 (2007/10/03)
We have developed a new strategy that uses the Kroehnke synthesis for the preparation of various substituted phenylpyridines in excellent yields (up to 88%). Starting with the appropriate commercially available acetophenone, a variety of phenylpyridines substituted by either electron-donating (i.e. methyl, methoxy) or -withdrawing groups (i.e. bromide, nitro) on the phenyl ring are obtained in a two-step synthesis. The corresponding functionalized cyclometalated ruthenium complexes can be prepared with unusually high yields by using methanol as reaction solvent. The electrochemical data of the complexes demonstrate the strong σ-donating character of the anionic phenylpyridine ligand. X-ray analyses of four complexes show a shortening of the Ru-C bond associated with the elongation of only one of the five Ru-N bonds (trans effect). Wiley-VCH Verlag GmbH & Co, KGaA, 2006.
Steric Enhancement of Resonance: Kinetics of the Reaction of Acetophenones with Pyridine and Iodine
Ganapathy, K.,Ramanujam, M.
, p. 701 - 703 (2007/10/02)
The kinetics of the reaction of a number of mono-, di- and tri-substituted acetophenones with pyridine and iodine at 30 deg C have been investigated.Evidence for steric enhancement of resonance is obtained from the rate constants of 3-substituted-4-methox
