14178-66-6Relevant academic research and scientific papers
Bi(OTf)3-Mediated (4+1) Annulation of α-Sulfonyl o-Hydroxyacetophenones with α-Hydroxy Arylketones to Access Sulfonyl 2-Aroylbenzofurans
Chang, Meng-Yang,Chen, Kuan-Ting
, p. 2594 - 2609 (2021/03/29)
In this paper, a high-yield, facile route for the scalable synthesis of sulfonyl 2-aroylbenzofurans via a Bi(OTf)3-mediated intermolecular double cyclocondensation of α-sulfonyl o-hydroxyacetophenones with substituted α-hydroxy arylketones under mild open-vessel reaction conditions is described. In the overall reaction, water is generated as the only byproduct. Various metal triflate-promoted reactions and conditions are investigated for the efficient one-pot (4+1) annulation reaction. (Figure presented.).
Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles
Gong, Julin,Hu, Kun,Shao, Yinlin,Li, Renhao,Zhang, Yetong,Hu, Maolin,Chen, Jiuxi
, p. 488 - 494 (2020/02/03)
The first example of the palladium-catalyzed tandem addition/cyclization of 2-(2-acylphenoxy)acetonitriles with arylboronic acids has been developed, providing a new strategy for the synthesis of 2-aroyl benzofurans with excellent chemoselectivity and wid
Rh(III)-Catalyzed and Solvent-Controlled Chemoselective Synthesis of Chalcone and Benzofuran Frameworks via Synergistic Dual Directing Groups Enabled Regioselective C-H Functionalization: A Combined Experimental and Computational Study
Yi, Wei,Chen, Weijie,Liu, Fu-Xiaomin,Zhong, Yuting,Wu, Dan,Zhou, Zhi,Gao, Hui
, p. 9508 - 9519 (2018/09/27)
By virtue of a synergistically dual-directing-group (the O-NHAc part and the hydroxyl group)-assisted strategy, the efficient and practical Rh(III)-catalyzed regioselective redox-neutral C-H functionalization of diverse N-phenoxyacetamides with propargyl alcohols has been realized, which led to the divergent synthesis of privileged benzofuran and chalcone frameworks in a solvent-controlled chemoselective manner. Experimental and computational studies reveal that the formation of the hydrogen bonding between dual directing groups and the subsequent coordination interaction between the hydroxyl group and the Rh(III) catalyst play a decisive role in promoting the regioselective migratory insertion of the alkyne moiety. Thereafter, two solvent-controlled switchable reaction pathways, which respectively involve tandem β-H elimination/hydrogen transfer/oxidative addition/C-O bond reductive elimination/oxidation (for low-polar solvents: path I-Ia via a RhIII-RhI-RhIII pathway) and oxidative addition/β-H elimination/hydrogen transfer/protonolysis (for high-polar solvents: path II-IIb via a RhIII-RhV-RhIII pathway), are followed to deliver the corresponding products with excellent chemoselectivity. Taken together, our results presented here not only give an expansion in the area of O-NHAc-directed C-H activations but also provide a rational basis for future development of synergistic dual DGs-enabled C-H functionalization reactions.
Fragmentation of 2-aroylbenzofuran derivatives by electrospray ionization tandem mass spectrometry
Dias, Herbert J.,Vieira, Tatiana M.,Crevelin, Eduardo J.,Donate, Paulo M.,Vessecchi, Ricardo,Crotti, Ant?nio E.M.
, p. 809 - 816 (2018/01/01)
We investigated the gas-phase fragmentation reactions of a series of 2-aroylbenzofuran derivatives by electrospray ionization tandem mass spectrometry (ESI-MS/MS). The most intense fragment ions were the acylium ions m/z 105 and [M+H–C6H6
Facile microwave-assisted synthesis of substituted benzofuran derivatives
Liu, Junqiang,Mi, Chenggen,Tang, Xuemei,Cao, Yuan,Li, Zicheng,Huang, Wencai
, p. 2083 - 2090 (2014/05/06)
A series of benzofuran derivatives have been synthesized by use of a microwave-assisted process. Substituted or unsubstituted ?- hydroxyacetophenone and salicylaldehyde reacted with ethyl bromoacetate, ω-bromoacetophenone, or chloroacetone under the action of potassium carbonate in DMF to yield substituted benzofuran derivatives. Compared with conventional heating, this microwave-assisted synthetic process has the advantages of more convenient operation, shorter reaction time, and higher yield.
A highly efficient ultrasound-promoted synthesis of 2,3-disubstituted benzo[b]furans via intramolecular C-C bond formation in ionic liquid[bmim]BF4 at room temperature
Yadav, Nisha,Hussain, Mohd. Kamil,Ansari, Mohd. Imran,Gupta, Puneet K.,Hajela, Kanchan
, p. 540 - 544 (2013/03/28)
An efficient ultrasound-promoted synthesis of 2,3-disubstituted benzo[b]furans in the ionic liquid [bmim]BF4 at room temperature is reported. 5-exo-dig carbanion-yne intramolecular cyclization is mediated using anhydrous K3PO4/
Efficient and connective assembly of highly functionalized benzofurans using o-hydroxyphenones and dichloroethylene
Schevenels, Florian,Marko, Istvan E.
, p. 1298 - 1301 (2012/05/31)
The preparation of highly functionalized benzofurans by a unique and connective transformation is reported. Base-catalyzed condensation of o-hydroxyphenones with 1,1-dichloroethylene generates the corresponding chloromethylene furans. These labile intermediates undergo a facile rearrangement into benzofuran carbaldehydes under mild acidic conditions.
Synthesis, antiproliferative activities and in vitro biological evaluation of novel benzofuransulfonamide derivatives
Yang, Li,Lei, Hua,Mi, Cheng-Gen,Liu, Huan,Zhou, Tian,Zhao, Ying-Lan,Lai, Xiao-Yun,Li, Zi-Cheng,Song, Hang,Huang, Wen-Cai
supporting information; experimental part, p. 5389 - 5392 (2011/10/12)
In a cell-based screen of novel antiproliferative agents, the hit compound 1a, which bears a benzofuransulfonamide scaffold, exhibited broad-spectrum antiproliferative activities against a panel of tumor cell lines. The promising in vitro antiproliferative activity and structural novelty of 1a prompted us to investigate the synthesis of five analogs of 1a and test their antiproliferative activities. The most potent analogue, 1h, exhibited enhanced antiproliferative activities compared with the parent 1a, and exhibited an IC50 value against NCI-H460 cells of 4.13 μM compared with 4.52 μM for the positive control cisplatin. Flow cytometric analysis revealed that 1h induces significant levels of apoptosis in NCI-H460 cells in vitro at low micromolar concentrations. These results suggest that 1a and analogs based on its benzofuransulfonamide scaffold may constitute a novel class of antiproliferative agents, which deserve further study.
DMAP-catalyzed cascade reaction: One-pot synthesis of benzofurans in water
Shang, Yongjia,Wang, Cuie,He, Xinwei,Ju, Kai,Zhang, Min,Yu, Shuyan,Wu, Jiaping
experimental part, p. 9629 - 9633 (2011/01/03)
A series of benzofurans were efficiently synthesized in good to excellent yields using 4-dimethylaminopyridine (DMAP) catalyzed cascade reaction between salicylaldehydes and halogenated ketones in water at 80 °C opened atmosphere.
Synthesis and?antifungal activities of?some?aryl [3-(imidazol-1-yl/triazol-1-ylmethyl) benzofuran-2-yl] ketoximes
Gündo?du-Karaburun, Nalan,Benkli, Kadriye,Tunali, Ya?mur,U?ucu, ümit,Demirayak, ?eref
, p. 651 - 656 (2007/10/03)
In this study, some aryl [3-(imidazol-1-yl/triazol-1-ylmethyl)benzofuran-2-yl] ketones, aryl (3-methyl-benzofuran-2-yl) ketoximes and aryl [3-(imidazol-1-yl/triazol-1-ylmethyl)benzofuran-2-yl] ketoximes were synthesised starting from 2-aryloyl-3-methyl-be
