25439-60-5Relevant articles and documents
Ethylene Dications Substituted with Electron-Donating Groups
Ohwada, Tomohiko,Shudo, Koichi
, p. 5227 - 5237 (1989)
Direct spectroscopic observations were made of substituted ethylene dications bearing ?-stabilizing groups such as an aryl, a hydroxy, or a methoxy group in a strong acid, trifluoromethanesulfonic acid (TFSA).Based on the spectroscopic evidence, we reached the following conclusions. (1) 1,1-Diaryl-2-hydroxy-2-methoxyethylene dications, 1,1-diaryl-2,2-dihydroxyethylene dications, and 1,1,2-triaryl-2-hydroxyethylene dications are discrete intermediates in the electrocyclization reaction to yield the fluorene and phenanthrol in TFSA. (2) Several dications bearing methoxy substituents on the aromatic rings are formed in trifluoroacetic acid (TFA). (3) NMR spectra suggested the nonplanar structures of O-protonated α-carbonyl diarylmethyl dications at the central C-C bond. (4) 1,2-Diaryl-1,2-dihydroxyethylene dications and 1-aryl-1,2,2-trihydroxyethylene dications are very stable.Ab initio MO calculations showed that 1,2-dihydroxyethylene dications are more stable than 1,1-dihydroxyethylene dications.
Natural product inspired library synthesis - Identification of 2,3-diarylbenzofuran and 2,3-dihydrobenzofuran based inhibitors of Chlamydia trachomatis
Saleeb, Michael,Mojica, Sergio,Eriksson, Anna U.,Andersson, C. David,Gylfe, ?sa,Elofsson, Mikael
supporting information, p. 1077 - 1089 (2017/12/15)
A natural product inspired library was synthesized based on 2,3-diarylbenzofuran and 2,3-diaryl-2,3-dihydrobenzofuran scaffolds. The library of forty-eight compounds was prepared by utilizing Pd-catalyzed one-pot multicomponent reactions and ruthenium-catalyzed intramolecular carbenoid C-H insertions. The compounds were evaluated for antibacterial activity in a panel of test systems including phenotypic, biochemical and image-based screening assays. We identified several potent inhibitors that block intracellular replication of pathogenic Chlamydia trachomatis with IC50 ≤ 3 μM. These new C. trachomatis inhibitors can serve as starting points for the development of specific treatments that reduces the global burden of C. trachomatis infections.
A one-pot domino C-H, C-C activation in coumarins: A fast track to 2,3-diaryl benzo[b]furans
Khoobi, Mehdi,Molaverdi, Fatemeh,Jafarpour, Farnaz,Abbasnia, Masoumeh,Kubicki, Maciej,Shafiee, Abbas
supporting information, p. 11713 - 11716 (2015/07/15)
An approach to synthesize 2,3-diaryl benzo[b]furans using coumarins and aryl bromides is developed. This state-of-the-art strategy capitalizes on a palladium-catalyzed one-pot decarbonylative diarylation of coumarins, paving the way to achieve biologicall
Palladium-catalyzed synthesis of benzofurans via C-H activation/oxidation tandem reaction and its application to the synthesis of decursivine and serotobenine
Guo, Lei,Zhang, Fengying,Hu, Weimin,Li, Lei,Jia, Yanxing
, p. 3299 - 3302 (2014/03/21)
A new palladium-catalyzed method for the synthesis of benzofurans by reaction of 2-hydroxystyrenes and iodobenzenes via a C-H activation/oxidation tandem reaction has been unprecedentedly discovered. By using this strategy, the overall synthetic efficienc
Structure-activity relationship of antiestrogens: A study using triarylbutenone, benzofuran, and triarylfuran analogues as models for triarylethylenes and triarylpropenones
Durani,Jain,Saeed,Dikshit,Durani,Kapil
, p. 1700 - 1707 (2007/10/02)
In a study of the structure-activity relationship (SAR) of antiestrogens use has been made of certain 1,2,3-triarylbutenones, of 2-arylbenzofurans carrying aryl or aroyl substituents at C3, and of 2,3,4-triarylfurans as conformationally constra
p-Methoxybenzoylmethylium Hexafluoroantimonate: the First Isolatable Carbonyl-substituted Carbenium Ion Salt
Takeuchi, Ken'ichi,Kitagawa, Toshikazu,Okamoto, Kunio
, p. 7 (2007/10/02)
The title compound (p-MeOC6H4)2(p-MeOC6H4CO)C+SbF6- has been prepared as a stable crystalline salt from the corresponding chloride and silver hexafluoroantimonate; when heated in 1,2-dichloroethane this cation affords 2,3-bis-(p-methoxyphenyl)-6-methoxybenzofuran (5) via cyclization.