25755-93-5Relevant academic research and scientific papers
Mechanistic understanding of a silver pyridylpyrrolide as a catalyst for 3 + 2 cyclization of a nitrile with diazo ester
Flores, Jaime A.,Pal, Kuntal,Carroll, Maria E.,Pink, Maren,Karty, Jonathan A.,Mindiola, Daniel J.,Caulton, Kenneth G.
, p. 1544 - 1552 (2014)
The trinuclear argentate complex Ag3(μ2-3,5- (CF3)2PyrPy)3 (PyrPy = 2,2′- pyridylpyrrolide) catalyzes the 3 + 2 cycloaddition of several NCR (R = Me, Ph, tBu) and N2CHCO2Et to disubstituted oxazoles, even in the presence of light and air. Structural and theoretical studies imply a three-coordinate silver carbene complex, (3,5-(CF3) 2PyrPy)Ag(CHCO2Et), to be responsible in a stepwise nitrile addition and cyclization step to form the heterocycle.
Synthesis and preliminary anti-inflammatory and anti-bacterial evaluation of some diflunisal aza-analogs
Carta, Davide,Brun, Paola,Dal Pra, Matteo,Bernabè, Giulia,Castagliuolo, Ignazio,Ferlin, Maria Grazia
, p. 1017 - 1032 (2018/06/27)
Our aim was to identify new multi-target compounds endowed with both anti-inflammatory and anti-bacterial activities for treatment of human infections. Diflunisal, a nonsteroidal anti-inflammatory agent, has recently been repurposed for its anti-virulence properties against methicillin-resistant Staphylococcus aureus. Effective synthesis of some aza-analogs of the anti-inflammatory drug diflunisal was carried out following the route involving key oxazole intermediates to obtain o- and m-hydroxypyridinecarboxylic acid derivatives. The newly synthesized diflunisal aza-analogs did not exhibit cytotoxic activity up to 80 μM and some of them exhibited anti-inflammatory activities, decreasing the levels of pro-inflammatory cytokines and prostaglandins induced by bacterial lipopolysaccharide in human primary macrophages. Ten of the diflunisal aza-analogs were found to have interesting antibacterial activity, sensitizing S. aureus, Streptococcus pyogenes, Enterococcus faecium, and Pseudomonas aeruginosa to the antibacterial effects of beta-lactam antibiotics and protein synthesis inhibitors.
Copper-Catalyzed Aerobic Oxidative [2 + 3] Cyclization/Aromatization Cascade Reaction: Atom-Economical Access to Tetrasubstituted 4,5-Biscarbonyl Imidazoles
Xie, Jialin,Huang, Yuanqiong,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
supporting information, p. 6056 - 6059 (2017/11/27)
An atom-economical method for accessing tetrasubstituted 4,5-biscarbonylimidazoles by reaction between glycine derivatives and 5-alkoxyoxazoles is reported. The method, which involves a copper-catalyzed aerobic oxidative [2 + 3] cyclization/aromatization
Copper-exchanged bentonite: A reusable catalysis for the formation of alkoxycarbonyl nitrile ylides under microwave irradiation
Bendedouche, Choukri Kamel,Benhaoua, Hadj
experimental part, p. 149 - 151 (2012/10/18)
Ethyldiazoacetate reacts as a carbene precursor in presence of copper exchanged bentonite. Reaction with excess nitrile gave oxazole derivatives. Their formation is explained by intramolecular 1,5-cyclisation of alkoxycarbonyl substituted nitrile ylide intermediate.
Synthesis and reactivity of 4-silylated oxazoles
Ducept, Pascal C.,Marsden, Stephen P.
, p. 692 - 294 (2007/10/03)
Treatment of (triethylsilyl)diazoacetates with rhodium(II) octanoate and a range of substituted nitriles generates trisubstituted oxazoles bearing a triethylsilyl group in the 4-position. Fluoride-mediated desilylation yields 3,5-disubstituted oxazoles, w
Regiospecific syntheses of the monomethylated 3-phenyldihydro-1,2,4-triazin-6(1H)-ones
Collins, David J.,Hughes, Timothy C.,Johnson, Wynona M.
, p. 463 - 468 (2007/10/03)
Unambiguous syntheses of four unreported monomethylated derivatives of 3-phenyldiliydro-1,2,4-triazin-6(1H)-ones, namely, the 1-methyl (2), 2-methyl (3), 4-methyl (4) and the imidic O-methyl derivative (5), are described. Regioselectivity was achieved for
Formation of Acyl-Substituted Nitrile Ylides by Rh2(OAc)4-Catalyzed Decomposition of α-Diazocarbonyl Compounds in Nitriles
Fukushima, Kazuaki,Ibata, Toshikazu
, p. 3469 - 3482 (2007/10/03)
The Rh2(OAc)4-catalyzed reactions of α-diazocarbonyl compounds in nitrile in the presence of dimethyl acetylenedicarboxylate (DMAD) gave oxazole and pyrrole derivatives.The formation of the oxazole derivatives is explained in terms of the 1,5-cyclization of an acyl-substituted nitrile ylide intermediate, and the formation of the pyrrole derivatives is explained by the 1,3-dipolar cycloaddition of the same intermediate with DMAD.The regiochemistry of the cycloaddition of the acyl-substituted nitrile ylide with methyl propiolate showed that the contribution of an allenyl-type resonance structure plays an important role in the acyl-substituted nitrile ylide reaction.
Formation and Reaction of Acyl Substituted Nitrile Ylide through the Rh2(OAc)4-Catalyzed Reaction of α-Diazocarbonyl Compounds with Benzonitrile
Ibata, Toshikazu,Fukushima, Kazuaki
, p. 2197 - 2200 (2007/10/02)
The rhodium(II) acetate-catalyzed reaction of α-diazocarbonyl compounds with benzonitrile and dimethyl acetylenedicarboxylate gave oxazoles and pyrrole-3,4-dicarboxylates through the 1,5-cyclization and 1,3-dipolar cycloaddition of the acyl substituted nitrile ylide intermediates generated by the reaction of ketocarbenoids with benzonitrile.
