31766-64-0Relevant academic research and scientific papers
Acid-promoted selective synthesis of trifluoromethylselenolated benzofurans with Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate
Liu, Juyan,Tian, Miaomiao,Li, Ankun,Ji, Liangshuo,Qiu, Di,Zhao, Xia
supporting information, (2021/02/01)
A Br?nsted acid-promoted trifluoromethylselenolation of benzofurans was disclosed by using Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate as a stable and easily prepared electrophilic trifluoromethylselenolating reagent. A wide range of SeCF3-substituted benzofuran derivatives were obtained in moderate to good yields with excellent regioselectivity. The tandem cyclization/trifluoromethylselenolation procedure of 1-methoxy-2-(arylethynyl)benzenes were also realized by engaging FeCl3 as the catalyst.
Porous organic polymer with: In situ generated palladium nanoparticles as a phase-transfer catalyst for Sonogashira cross-coupling reaction in water
Dong, Ying,Chen, Yun-Qi,Jv, Jing-Jing,Li, Yue,Li, Wen-Han,Dong, Yu-Bin
, p. 21671 - 21678 (2019/07/30)
A new Pd nanoparticle loaded and imidazolium-ionic liquid decorated organic polymer of Pd@PTC-POP was readily fabricated via a Pd(PPh3)4 catalysed in situ one-pot Suzuki cross-coupling reaction between imidazolium attached dibromoben
Molecular Interactions Control Quantum Chain Reactions toward Distinct Photoresponsive Properties of Molecular Crystals
Gong, Yanjun,Zhang, Yifan,Xiong, Wei,Zhang, Ke,Che, Yanke,Zhao, Jincai
supporting information, p. 10649 - 10652 (2017/08/15)
In this work, we fabricated four diphenylcyclopropenone (DPCP) crystals, which involved various molecular interactions encoded in individual molecular structures 1-4. On the basis of crystalline structural analysis and photoresponsive characterization of
Iridium-Catalyzed Intramolecular Methoxy C?H Addition to Carbon–Carbon Triple Bonds: Direct Synthesis of 3-Substituted Benzofurans from o-Methoxyphenylalkynes
Torigoe, Takeru,Ohmura, Toshimichi,Suginome, Michinori
supporting information, p. 10415 - 10419 (2016/07/21)
Catalytic hydroalkylation of an alkyne with methyl ether was accomplished. Intramolecular addition of the C?H bond of a methoxy group in 1-methoxy-2-(arylethynyl)benzenes across a carbon–carbon triple bond took place efficiently either in toluene at 110 °C or in p-xylene at 135 °C in the presence of an iridium catalyst. The initial 5-exo cyclization products underwent double-bond migration during the reaction to give 3-(arylmethyl)benzofurans in high yields.
Palladium nanoparticles catalyzed Sonogashira reactions for the one-pot synthesis of symmetrical and unsymmetrical diarylacetylenes
Mandali, Pavan Kumar,Chand, Dillip Kumar
, p. 40 - 44 (2014/02/14)
A variety of symmetrical and unsymmetrical diarylacetylenes are synthesized by ligand-free palladium nanoparticles catalyzed copper-free and amine-free Sonogashira cross-coupling reactions between aryl iodides and trimethylsilylacetylene (TMSA) under mild reaction conditions.
Design and synthesis of ERα/ERβ selective coumarin and chromene derivatives as potential anti-breast cancer and anti-osteoporotic agents
Hussain, M. Kamil,Ansari, M. Imran,Yadav,Gupta, Puneet K.,Gupta,Saxena,Fatima,Manohar,Kushwaha,Khedgikar,Gautam,Kant, Ruchir,Maulik,Trivedi,Dwivedi,Kumar, K. Ravi,Saxena,Hajela
, p. 8828 - 8845 (2014/03/21)
Several new coumarin and chromene prototype derivatives have been synthesised and evaluated for their ERα and ERβ selective activity. Coumarin prototype compounds 18 & 19 were found to be ERα selective and the most active, exhibiting potential antiproliferative activity against both ER +ve & ER -ve breast cancer cell lines. The surprise finding of the series, however, are the novel prototype III chromenes 45 & 46, with aroyl substitution at the 6th position. Both the compounds have shown potent antiproliferative activity against both the breast cancer cell lines, promote alkaline phosphatase activity, enhance osteoblast mineralization in vitro, significantly decrease ERE-ERα dependent transactivation and induce ERβ activity. This specific upregulation of ERβ isoform activity of compound 45 may be responsible for the antiosteoporotic activity at picomolar concentration. In addition, both the compounds were also devoid of any estrogenic activity, which correlates to their antiestrogenic behaviour in the two breast cancer cell lines. Assessment of selectivity using specific SiRNAs for ERα and ERβ revealed that most of the compounds showed ERα and ERβ-mediated action, except compound 28, which showed selectivity to ERα only. Computational docking analysis of active compounds 18 and 45 was conducted to correlate the interaction with the two receptors and it was found that the docked conformations of the coumarin prototype, compound 18 at ERα and ERβ active sites were more or less superimposable on each other. However, the unique orientation of the aminoalkoxy side chain of novel chromene (prototype III) compound 45 in the ERβ binding cavity may be responsible for its potential biological response. The Royal Society of Chemistry.
Synthesis of polysubstituted benzofuran derivatives as novel inhibitors of parasitic growth
Thévenin, Marion,Thoret, Sylviane,Grellier, Philippe,Dubois, Jo?lle
supporting information, p. 4885 - 4892 (2013/09/02)
A series of polysubstituted benzofuran derivatives was easily and rapidly prepared using a tandem Sonogashira coupling/cyclization reaction. Subsequent acylation afforded a small library of 39 new compounds that were assayed in cellulo on Plasmodium falci
Base-free palladium-catalyzed sonogashira coupling using organogold complexes
Pankajakshan, Sreekumar,Loh, Teck-Peng
experimental part, p. 2291 - 2295 (2012/06/30)
Turn to gold: An effective protocol for base-free Sonogashira coupling reactions using organogold complexes as nucleophilic partners has been developed. The palladium-catalyzed methodology offers a general synthesis of aryl-alkynes under operationally simple conditions in good to excellent yields. Copyright
Can polarization of triple bond in tolanes be deduced from 13C NMR shifts? Re-evaluation of factors affecting regiochemistry of the palladium-catalyzed hydrostannation of alkynes
Rubin, Michael,Trofimov, Alexander,Gevorgyan, Vladimir
, p. 10243 - 10249 (2007/10/03)
Polarization of the triple bond in a series of differently substituted ortho and para-tolanes has been studied by NMR and computational methods in order to examine if 13C NMR data can be effectively used for the assessment of electronic polarization of a triple bond in diarylacetylenes. DFT calculations of both natural charges and NMR properties revealed that chemical shifts concur with effective charges on sp-carbon atoms in para-tolanes, whereas in ortho-analogues magnetic anisotropy complicates the analysis making 13C NMR data inapplicable for ascribing triple bond polarization. The obtained information was used to reevaluate factors affecting the regiochemistry of the Pd-catalyzed hydrostannation of the triple bond in tolanes. Computational study on the polarization of triple bonds taken together with the experimental data on hydrostannation of various mono- and disubstituted tolanes bearing para- and ortho-substituents demonstrated that the regioselectivity of hydrostannation is governed by a combination of electronic and steric factors. In para-tolanes, the electronic effect prevails and α- and β-vinylstannanes are obtained predominantly for substrates with electron-withdrawing and electron-donating groups, respectively. In the ortho-series, steric factors dominate over electronics and α-isomers are produced with high selectivity regardless of the substituents' nature. However, it was found that in disubstituted "push-pull" tolanes steric control of an ortho-group can be overruled by the very strong electronic effect of an electron-withdrawing substituent in para-position.
Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization
Yue, Dawei,Yao, Tuanli,Larock, Richard C.
, p. 10292 - 10296 (2007/10/03)
2,3-Disubstituted benzo[b]furans are readily prepared under very mild reaction conditions by the palladium/copper-catalyzed cross-coupling of various o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization with I2, PhSeCl, Or
