32364-30-0Relevant articles and documents
Synthesis of Quinoxaline-Linked Bis(Benzimidazolium) Salts and Their Catalytic Application in Palladium-Catalyzed Direct Arylation of Heteroarenes
Kalo?lu, Murat,?ahan, Mehmet Hanifi,Dü?ünceli, Serpil Demir,?zdemir, ?smail
, (2021/09/13)
Abstract: In this study, quinoxaline-linked bis(benzimidazolium) salts were synthesized as bis-N-heterocyclic carbene (NHC) precursors. These bis(NHC) precursors were used as multidentate ligands for the construction of bi(hetero)aryls by palladium-cataly
Gold(I)-Catalyzed Reactivity of Furan-ynes with N-Oxides: Synthesis of Substituted Dihydropyridinones and Pyranones
Maranzana, Andrea,Marra, Francesco,Nejrotti, Stefano,Prandi, Cristina,Priola, Emanuele
supporting information, p. 8295 - 8307 (2021/07/02)
The reactivity of "furan-ynes"in combination with pyridine and quinoline N-oxides in the presence of a Au(I) catalyst, has been studied, enabling the synthesis of three different heterocyclic scaffolds. Selective access to two out of the three possible products, a dihydropyridinone and a furan enone, has been achieved through the fine-tuning of the reaction conditions. The reactions proceed smoothly at room temperature and open-air, and were further extended to a broad substrate scope, thus affording functionalized dihydropyridinones and pyranones.
End-Capping Groups for Small-Molecule Organic Semiconducting Materials: Synthetic Investigation and Photovoltaic Applications through Direct C–H (Hetero)arylation
Lu, Te-Jui,Lin, Po-Han,Lee, Kun-Mu,Liu, Ching-Yuan
, p. 111 - 123 (2017/01/14)
A Pd-catalyzed C–H (hetero)arylation methodology has been optimized for the efficient synthesis of various useful end-capping groups that are widely applied in small-molecule optoelectronic materials. We report herein the synthesis of a broad scope of target molecules ranging from donor-type through acceptor-type to hybrid-type end-capping groups. To demonstrate their application in dye-sensitized solar cells, we have designed two new D–A–π–A′-type organic sensitizers (CYL-3 and CYL-4), which were synthesized in a step-economic manner by sequential C–H arylations using the facilely obtained end-capping groups. The devices based on CYL-3 and CYL-4 give Vocvalues of 0.67–0.71 V, Jscvalues of 10.07–11.63 mA cm–2, and FF values of 70.6–72.9 %, which correspond to overall power conversion efficiencies of 4.76–6.02 %. This work is expected to become a practical synthetic alternative allowing materials scientists to access small-molecule organic materials in fewer synthetic transformations.
Sequential one pot double C[sbnd]H heteroarylation of thiophene using bromopyridines to synthesize unsymmetrical 2,5-bipyridylthiophenes
Kieffer, Charline,Babin, Victor,Jouanne, Marie,Slimani, Ikram,Berhault, Yohann,Legay, Rémi,Sopková-de Oliveira Santos, Jana,Rault, Sylvain,Voisin-Chiret, Anne Sophie
, p. 5509 - 5516 (2017/08/22)
We present C[sbnd]H heteroarylation reactions between thiophene and variously substituted bromopyridines. The objective was to synthesize unsymmetrical 2,5-bipyridylthiophenes. We studied the reaction conditions allowing to a sequential one-pot double C[sbnd]H heteroarylation, in a view to introduce two different pyridyl moieties at positions 2 and 5 of the thiophene ring using bromopyridines. 11 original unsymmetrical 2,5-bipyridylthiophenes were synthesized and characterized, including 2,5-di(pyridin-2-yl)thiophenes for which the preparation by classical cross-coupling reactions is challenging. Finally, with the additional synthesis of both an unsymmetrical 2,5-biarylthiophene and an original pyrimidin-thiophene-furan scaffold, we shown that our methodology was also an efficient tool to access to new heterocyclic sequences.
Efficient synthesis of RITA and its analogues: Derivation of analogues with improved antiproliferative activity via modulation of p53/miR-34a pathway
Lin, Jinshun,Jin, Xiuli,Bu, Yiwen,Cao, Deliang,Zhang, Nannan,Li, Shangfu,Sun, Qinsheng,Tan, Chunyan,Gao, Chunmei,Jiang, Yuyang
, p. 9734 - 9746 (2013/01/16)
A novel approach to synthesize RITA by practical palladium-catalyzed C-C bond-forming Suzuki reactions at room temperature was developed, which was used for deriving a series of substituted tricyclic α-heteroaryl (furan/thiophene) analogues of RITA under mild conditions. These novel analogues showed notable antiproliferative activity against cancer cell lines with wild-type p53 (i.e., HCT116, A549, MCF-7 and K562), but much less activity in HCT116/p53-/- cells. In particular, compound 1f demonstrated promising antiproliferative activity compared to RITA, with IC50 = 28 nM in MCF-7 vs. 54 nM for RITA, and cancer cell selectivity. Compound 1f markedly activated p53 in HCT116 cells at 100 nM, triggering apoptosis. Importantly, we found that both RITA and compound 1f induced G 0/G1 cell cycle arrest by up-regulating miR-34a, which in turn down-regulated the expression of cell cycle-related proteins CDK4 and E2F1. In summary, this study reports an effective synthetic approach for RITA and its analogues, and elucidates a novel antiproliferative mechanism of these compounds. The Royal Society of Chemistry 2012.
Room-temperature Suzuki-Miyaura coupling of heteroaryl chlorides and tosylates
Yang, Junfeng,Liu, Sijia,Zheng, Jian-Feng,Zhou, Jianrong
supporting information, p. 6248 - 6259,12 (2020/09/16)
Suzuki-Miyaura coupling of heteroaryls is an important method for the preparation of compound libraries for medicinal chemistry and materials research. Although many catalysts have been developed, none of them have been generally applicable to the coupling reactions of heteroaryl chlorides and tosylates at room temperature. We discovered that a catalyst combination of Pd(OAc)2 and XPhos (2-dicyclohexylphosphanyl-2',4',6'- triisopropylbiphenyl) could efficiently catalyze these couplings. Besides the choice of catalyst, the use of hydroxide bases in an aqueous alcoholic solvent was essential for fast couplings. These conditions promoted fast release of active catalyst (XPhos)Pd0, and accelerated the transmetalation in the catalytic cycle. Most of the major families of heteroaryl chlorides (31 examples) and tosylates (17 examples) reached full conversion within minutes to hours at room temperature. The method could be easily scaled up for gram-scale synthesis. Furthermore, we examined the relative reactivity of coupling partners in whole reactions. Electron-rich heteroaryl chlorides and tosylates reacted more slowly than electron-deficient ones, in the order of indole, pyrrole furan, thiophene > pyridine. Similarly, electron-deficient arylboronic acids were less reactive than electron-neutral and electron-rich ones. The reactivity trends from this study can help to choose appropriate coupling partners for Suzuki reactions.
An efficient synthesis of 5′-(4-cyanophenyl)-2,2′-bifuran-5- carbonitrile and analogues
Ismail, Mohamed A.
, p. 733 - 737 (2007/10/03)
5′-(4-Cyanophenyl)-2,2‰-bifuran-5-carbonitrile (6a) was prepared by two approaches. The first approach involves four steps, employs Stille coupling conditions utilising 2-tributylstannylfuran and 5-bromofuran-2-carboxaldehyde to furnish 3a in excellent yi
5-formyl-2-furylboronic acid as a versatile bifunctional reagent for the synthesis of π-extended heteroarylfuran systems
Parry, Paul R.,Bryce, Martin R.,Tarbit, Brian
, p. 1447 - 1449 (2007/10/03)
5-Formyl-2-furylboronic acid reacts cleanly with a range of heteroaryl bromides under Suzuki-Miyaura cross-coupling conditions to produce 2-formyl-5-heteroarylfuran derivatives. Subsequent Wittig olefination reactions afford π-conjugated alkene-pyridyl-furan derivatives.
Gamma-hydroxy-2-(fluoroalkylaminocarbonyl)-1-piperazinepentanamides and uses thereof
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Page/Page column 128, (2010/01/31)
γ-Hydroxy-2-(fluoroalkylaminocarbonyl)-1-piperazinepentanamide compounds are inhibitors of HIV protease and inhibitors of HIV replication. These compounds are useful in the prevention or treatment of infection by HV and the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described. These compounds are effective against HIV viral mutants which are resistant to HIV protease inhibitors currently used for treating AIDS and HIV infection.
A practical one-pot synthesis of 5-aryl-2-furaldehydes
McClure,Roschangar,Hodson,Millar,Osterhout
, p. 1681 - 1685 (2007/10/03)
A useful one-pot synthesis of 5-aryl-2-furaldehydes via palladium-mediated Suzuki coupling of aryl halides with in situ generated 5-(diethoxymethyl)-2-furylboronic acid is described. The procedure has general applicability, delivers high yields, and is amenable to scale-up.
