112404-04-3Relevant articles and documents
Synthesis of (Z)-N-hydroxy-3-methoxy-3-phenylacrylamide as new selective inhibitor of hepatitis C virus replication
Kozlov,Kleymenova,Konduktorov,Malikova,Kamarova,Novikov,Kochetkov
, p. 191 - 197 (2016)
According to recently published results, cinnamic hydroxamic acid (CHA) inhibits replication of hepatitis C virus (HCV). We synthesized a structural analogue of CHA, i.e., (Z)-N-hydroxy-3-methoxy3-phenylacrylamide, which inhibited HCV replication five tim
A metal-free iodine-mediated conversion of hydroxamates to esters
Ghosh, Subhankar,Banerjee, Jeet,Ghosh, Rajat,Chattopadhyay, Shital K.
, p. 1353 - 1360 (2020/03/30)
A metal-, oxidant-, and additive-free conversion of hydroxamates to esters have been achieved using molecular iodine as the reagent using a novel but not-so-explored heron-type rearrangement. The reaction proceeds with almost equal facility with substrates having either electron-donating or electron-withdrawing substituent. Similarly, α,?-unsaturated, and sterically hindered ortho-substituted hydroxamates also undergo the desired transformation smoothly.
Palladium-Catalyzed Deaminative Phenanthridinone Synthesis from Aniline via C-H Bond Activation
Yedage, Subhash L.,Bhanage, Bhalchandra M.
supporting information, p. 4103 - 4111 (2016/06/09)
This work reports palladium-catalyzed phenanthridinone synthesis using the coupling of aniline and amide by formation of C-C and C-N bonds in a one-pot fashion via dual C-H bond activation. It involves simultaneous cleavage of four bonds and the formation of two new bonds. The present protocol is ligand-free, takes place under mild reaction conditions, and is environmentally benign as nitrogen gas and water are the only side products. This transformation demonstrates a broad range of aniline and amide substrates with different functional groups and has been scaled up to gram level.
Pd-Catalyzed α-Selective C-H Functionalization of Olefins: En Route to 4-Imino-β-Lactams
Kong, Wei-Jun,Liu, Yue-Jin,Xu, Hui,Chen, Yan-Qiao,Dai, Hui-Xiong,Yu, Jin-Quan
, p. 2146 - 2149 (2016/03/05)
Pd-catalyzed α-olefinic C-H activation of simple α,β-unsaturated olefins has been developed. 4-imino-β-lactam derivatives were readily synthesized via activation of α-olefinic C-H bonds with excellent cis stereoselectivity. A wide range of heterocycles at the β-position are compatible with this reaction. The product of 4-imino-β-lactam derivatives can be readily converted to 2-aminoquinoline which exists extensively in pharmaceutical drugs and natural products.
Copper-catalyzed C-N bond formation through C-H/N-H activation: A novel approach to the synthesis of multisubstituted ureas
Jiang, Honglai,Lin, Aijun,Zhu, Chengjian,Cheng, Yixiang
supporting information, p. 819 - 821 (2013/02/23)
A copper-catalyzed cross-dehydrogenative coupling reaction that involves C-H activation of formamides and N-H activation of N-alkoxy amides has been developed. This protocol affords a novel approach to the synthesis of multisubstituted ureas under mild co
Identification of cinnamic acid derivatives as novel antagonists of the prokaryotic proton-gated ion channel GLIC
Prevost, Marie S.,Delarue-Cochin, Sandrine,Marteaux, Justine,Colas, Claire,Van Renterghem, Catherine,Blondel, Arnaud,Malliavin, Thérèse,Corringer, Pierre-Jean,Joseph, Delphine
, p. 4619 - 4630 (2013/07/19)
Pentameric ligand gated ion channels (pLGICs) mediate signal transduction. The binding of an extracellular ligand is coupled to the transmembrane channel opening. So far, all known agonists bind at the interface between subunits in a topologically conserved "orthosteric site" whose amino acid composition defines the pharmacological specificity of pLGIC subtypes. A striking exception is the bacterial proton-activated GLIC protein, exhibiting an uncommon orthosteric binding site in terms of sequence and local architecture. Among a library of Gloeobacter violaceus metabolites, we identified a series of cinnamic acid derivatives, which antagonize the GLIC proton-elicited response. Structure-activity analysis shows a key contribution of the carboxylate moiety to GLIC inhibition. Molecular docking coupled to site-directed mutagenesis support that the binding pocket is located below the classical orthosteric site. These antagonists provide new tools to modulate conformation of GLIC, currently used as a prototypic pLGIC, and opens new avenues to study the signal transduction mechanism.
Tandem-type Pd(ii)-catalyzed oxidative Heck reaction/intramolecular C-H amidation sequence: A novel route to 4-aryl-2-quinolinones
Inamoto, Kiyofumi,Kawasaki, Junpei,Hiroya, Kou,Kondo, Yoshinori,Doi, Takayuki
, p. 4332 - 4334 (2012/05/20)
A novel catalytic method for synthesizing 4-aryl-2-quinolinones is reported. The process involves two mechanistically independent, sequential Pd(ii)-catalyzed reactions - the oxidative Heck reaction and the intramolecular C-H amidation - both of which smoothly proceed in the presence of a single catalytic system in a one-pot manner. The Royal Society of Chemistry 2012.
Imino 1,2-Wittig rearrangement of hydroximates and its application to synthesis of cytoxazone
Miyata, Okiko,Koizumi, Tomoko,Asai, Hiroshi,Iba, Ryuichi,Naito, Takeaki
, p. 3893 - 3914 (2007/10/03)
The imino 1,2-Wittig rearrangement of hydroximates provides a novel method for the construction of 2-hydroxyoxime ethers. Upon treatment with LDA, Z-hydroximates smoothly underwent stereoselective rearrangement to give Z-2-hydroxyoxime ethers in good yield, which were converted into amino alcohols. On the other hand, the rearrangement of E-hydroximates gave a mixture of E- and Z-2-hydroxyoxime ethers. This method was successfully applied to a practical synthesis of cytoxazone.
Direct synthesis of hydroxamates from carboxylic acids using 2-mercaptopyridone-1-oxide-based thiouronium salts
Bailén, Miguel A.,Chinchilla, Rafael,Dodsworth, David J.,Nájera, Carmen
, p. 5013 - 5016 (2007/10/03)
Tetrafluoroborate and hexafluorophosphate thiouronium salts derived from 2-mercaptopyridone-1-oxide and tetramethylurea (TOTT and HOTT) or N,N′-dimethylpropyleneurea (TODT and HODT) convert carboxylic acids to Weinreb amides and N-methoxy or N-benzoxyamides in high yields by reaction with N,O-dimethylhydroxylamine and O-methyl- or O-benzyl-hydroxylamine hydrochlorides, respectively, in the presence of triethylamine or DIEA.
Radical Cyclization in Heterocycle Synthesis. 11. A Novel Synthesis of α,β-Disubstituted γ-Lactones via Sulfanyl Radical Addition-Cyclization Using Hydroximates as a Tether
Miyata, Okiko,Nishiguchi, Atsuko,Ninomiya, Ichiya,Aoe, Keiichi,Okamura, Kimio,Naito, Takeaki
, p. 6922 - 6931 (2007/10/03)
A combination of sulfanyl radical addition-cyclization of dienes connected with hydroximates and subsequent conversion of the resulting cyclic hydroximate to the lactones provides a novel method for the construction of α,β-disubstituted γ-lactones. Upon treatment with thiophenol in the presence of AIBN, dienes connected with hydroximates smoothly underwent sulfanyl radical addition-cyclization to give cyclic cis- and trans-hydroximates. Hydrolysis of cyclic hydroximates gave the desired cis- and trans-lactones in high yield. This method was successfully applied to the practical synthesis of (±)-oxo-parabenzlactone.
