86607-76-3Relevant academic research and scientific papers
Quinoline Ligands Improve the Classic Direct C?H Functionalisation/Intramolecular Cyclisation of Diaryl Ethers to Dibenzofurans
Mackey, Katrina,Jones, David J.,Pardo, Leticia M.,McGlacken, Gerard P.
supporting information, p. 495 - 498 (2021/01/12)
The C?H functionalisation approach to the synthesis of dibenzofurans is hampered by a number of problems. Herein we describe the evolution of a cheap, bench stable quinoline ligand, which obviates most of the current limitations and allows for a high yielding synthesis of a range of valuable dibenzofurans. Dibenzofurans are important motifs in natural products and compounds with wide biological activity.
Functionalized 2,1-benzothiazine 2,2-dioxides as new inhibitors of Dengue NS5 RNA-dependent RNA polymerase
Cannalire, Rolando,Tarantino, Delia,Astolfi, Andrea,Barreca, Maria Letizia,Sabatini, Stefano,Massari, Serena,Tabarrini, Oriana,Milani, Mario,Querat, Gilles,Mastrangelo, Eloise,Manfroni, Giuseppe,Cecchetti, Violetta
supporting information, p. 1667 - 1676 (2017/11/17)
Over recent years, many RNA viruses have been “re-discovered” including life-threatening flaviviruses, such as Dengue, Zika, and several encephalitis viruses. Since no specific inhibitors are currently available to treat these infections, there is a pressing need for new therapeutics. Among the flaviviral proteins, NS5 RNA-dependent RNA polymerase (RdRp) represents a validated target being essential for viral replication and it has no human analog. To date, few NS5 RdRp inhibitor chemotypes have been reported and no inhibitors are currently in clinical development. In this context, after an in vitro screening against Dengue 3 NS5 RdRp of our in-house HCV NS5B inhibitors focused library, we found that 2,1-benzothiazine 2,2-dioxides are promising non-nucleoside inhibitors of flaviviral RdRp with compounds 8 and 10 showing IC50 of 0.6 and 0.9 μM, respectively. Preliminary structure-activity relationships indicated a key role for the C-4 benzoyl group and the importance of a properly functionalized C-6 phenoxy moiety to modulate potency. Compound 8 acts as non-competitive inhibitor and its proposed pose in the so-called N pocket of the RdRp thumb domain allowed to explain the key contribution of the benzoyl and the phenoxy moieties for the ligand binding.
Ultrasound-promoted intramolecular direct arylation in a capillary flow microreactor
Zhang, Lei,Geng, Mei,Teng, Peng,Zhao, Dan,Lu, Xi,Li, Jian-Xin
experimental part, p. 250 - 256 (2012/04/23)
An intramolecular direct arylation of various aryl bromides was performed using ultrasonic irradiation and a continuous flow capillary microreactor. The present procedure provided a higher functional group tolerance, ligand-free, milder reaction condition
One-pot Synthesis of Dibenzofurans via SNAr and Subsequent Ligand-free Palladium-catalyzed Intramolecular Aryl-aryl Cross-coupling Reactions under Microwave Irradiation
Che, Zhiping,Xu, Hui
experimental part, p. 833 - 836 (2011/10/05)
An efficient one-pot synthesis of dibenzofurans, via SNAr reaction of aryl halides and ortho-bromophenols in the presence of anhydrous K2CO 3 and subsequent ligand-free palladium-catalyzed intramolecular aryl-aryl cross-coupling cyclization under microwave irradiation, is described.
Synthesis of dibenzofurans directly from aryl halides and ortho-bromophenols via one-pot consecutive SNAr and intramolecular palladium-catalyzed aryl-aryl coupling reactions
Xu, Hui,Fan, Ling-Ling
experimental part, p. 1496 - 1498 (2009/10/16)
A series of dibenzofurans were efficiently and conveniently synthesized via one-pot consecutive C(sp2)-O bond formation reaction (SNAr) in the presence of anhydrous K2CO3, followed by C(sp 2)-C(sp2) b
PALLADIUM-CATALYSED CYCLISATION OF 2-SUBSTITUTED HALOGENOARENES BY DEHYDROHALOGENATION
Ames, D.E.,Opalko, A.
, p. 1919 - 1926 (2007/10/02)
Cyclodehydrohalogenation mediated by various palladium catalysts and solvents with different bases (the most generally satisfactory system being palladium(II) acetate in NN-dimethylacetamide (DMA) with sodium carbonate as base) has been examined as a route to some heterocyclic systems.Whereas dehydrogenative cyclisation processes require stoichiometric amounts of palladium(II) reagent, the present procedure involves only catalytic amounts (0.1 molar proportion, or less), of palladium compound.The preparation of dibenzofuran, carbazole, fluorenone, 6H-dibenzothiazine-5,5-dioxide, 6H-dibenzopyran and benzofuranopyridine derivatives is described.The cyclisation of 3-benzamido-2-chloropyridine to 6-hydroxybenzonaphthiridine illustrates the regiospecificity of the process.
