7197-02-6Relevant academic research and scientific papers
Dehydrative condensation of carbonyls with non-acidic methylenes enabled by light: Synthesis of benzofurans
Liu, Wenbo,Chen, Ning,Yang, Xiaobo,Li, Lu,Li, Chao-Jun
supporting information, p. 13120 - 13123 (2016/11/09)
Condensation of carbonyls with non-acidic methylenes such as those adjacent to heteroatoms and allylic types to generate CC bonds is challenging but highly desirable. Inventing novel methods that can accomplish such condensations can enrich synthetic chemists' toolbox. Herein, we report a simple, clean, and high yielding protocol promoted by light to achieve condensation of non-acidic methylenes with carbonyls. As examples to demonstrate the power of this methodology, one class of ubiquitous and highly important heterocycles, i.e. benzofurans, were synthesized with broad functional group compatibility. Furthermore, intermolecular condensations were also briefly investigated.
3-Carboxamido-5-aryl-isoxazoles as new CB2 agonists for the treatment of colitis
Tourteau, Aurélien,Andrzejak, Virginie,Body-Malapel, Mathilde,Lemaire, Lucas,Lemoine, Amélie,Mansouri, Roxane,Djouina, Madjid,Renault, Nicolas,El Bakali, Jamal,Desreumaux, Pierre,Muccioli, Giulio G.,Lambert, Didier M.,Chavatte, Philippe,Rigo, Beno?t,Leleu-Chavain, Natascha,Millet, Régis
, p. 5383 - 5394 (2013/09/02)
Recent investigations showed that anandamide, the main endogenous ligand of CB1 and CB2 cannabinoid receptors, possesses analgesic, antidepressant and anti-inflammatory effects. In the perspective to treat inflammatory bowel disease (IBD), our approach was to develop new selective CB2 receptor agonists without psychotropic side effects associated to CB1 receptors. In this purpose, a new series of 3-carboxamido-5- aryl-isoxazoles, never described previously as CB2 receptor agonists, was designed, synthesized and evaluated for their biological activity. The pharmacological results have identified great selective CB2 agonists with in vivo anti-inflammatory activity in a DSS-induced acute colitis mouse model.
Use of diethoxymethane as a solvent for phase transfer-catalyzed O -alkylation of phenols
Coleman, M. Todd,Leblanc, Gabriel
experimental part, p. 732 - 736 (2011/07/07)
The effectiveness of diethoxymethane (DEM) as a solvent for O-alkylation of a variety of phenols under phase transfer conditions has been examined and evaluated. The reaction between 4-methoxy phenol and benzyl chloride was selected to compare reaction rates in various solvents and the efficiency of various PTCs. This reaction was further studied to develop a commercially amenable process complete with recycle streams and efficient product isolation. DEM is a good solvent for these types of phase transfer-catalyzed reactions and can be considered as an alternative solvent for dichloromethane and toluene.
Discovery of α,γ-Diketo Acids as Potent Selective and Reversible Inhibitors of Hepatitis C Virus NS5b RNA-Dependent RNA Polymerase
Summa, Vincenzo,Petrocchi, Alessia,Pace, Paola,Matassa, Victor G.,De Francesco, Raffaele,Altamura, Sergio,Tomei, Licia,Koch, Uwe,Neuner, Philippe
, p. 14 - 17 (2007/10/03)
α,γ-Diketo acids (DKA) were discovered from screening as selective and reversible inhibitors of hepatitis C virus NS5b RNA-dependent RNA polymerase. The diketo acid moiety proved essential for activity, while substitution on the γ position was necessary for selectivity and potency. Optimization led to the identification of a DKA inhibitor of NS5b polymerase with IC50 = 45 nM, one of the most potent HCV NS5b polymerase inhibitors reported.
Ruthenium porphyrin catalyzed intramolecular carbenoid C-H insertion. Stereoselective synthesis of Cis-disubstituted oxygen and nitrogen heterocycles
Cheung, Wai-Hung,Zheng, Shi-Long,Yu, Wing-Yiu,Zhou, Guo-Chuan,Che, Chi-Ming
, p. 2535 - 2538 (2007/10/03)
(Matrix presented) A ruthenium porphyrin-catalyzed stereoselective intramolecular carbenoid C-H insertion is described. Using [Ru II(TTP)(CO)] as catalyst, aryl tosylhydrazones are converted to 2,3-dihydrobenzofurans, 2,3-dihydroindoles, and β-lactams in good yields and remarkable cis selectivity (up to 99%). Enantioselective synthesis of 2,3-dihydrobenzofurans is also achieved with [RuII(D 4-Por*)(CO)] as catalyst, and up to 96% ee is attained.
Pyrazole and Isoxazole Derivatives as New, Potent, and Selective 20-Hydroxy-5,8,11,14-eicosatetraenoic Acid Synthase Inhibitors
Nakamura, Toshio,Sato, Masakazu,Kakinuma, Hiroyuki,Miyata, Noriyuki,Taniguchi, Kazuo,Bando, Kagumi,Koda, Ayumi,Kameo, Kazuya
, p. 5416 - 5427 (2007/10/03)
In a previous paper, we reported the N-hydroxyformamidine derivative HET0016 as a potent and selective 20-HETE synthase inhibitor. Despite its attraction as a potential therapeutic agent for cerebral diseases, the preparation of an injectable formulation
Gas-Liquid Phase-transfer Synthesis of Phenyl Ethers and Sulphides with Carbonate as Base and Carbowax as Catalyst
Angeletti, Enrico,Tundo, Pietro,Venturello, Paolo
, p. 1137 - 1142 (2007/10/02)
When a mixture of a phenol (or thiol) and an alkyl halide is passed, in the gaseous state, through a solid bed of potassium carbonate (or sodium hydrogencarbonate) and catalytic amounts of Carbowax 6000, contained in a glass column at 170 deg C, the corresponding ethers (or sulphides) may be collected at the outlet.The Carbowax acts in a similar manner to the crown ethers used in solid-liquid phase-transfer catalysis.The potassium carbonate-Carbowax combination allows the generation of anions up to pKa of ca. 12.The catalysis mechanism is discussed and the synthesis of several ethers and thioethers is reported, some of which are obtained only with difficulty by normal liquid-liquid phase-transfer catalysis.
