3558-24-5Relevant academic research and scientific papers
Trans-Aminoboration across Internal Alkynes Catalyzed by B(C6F5)3 for the Synthesis of Borylated Indoles
Yuan, Kang,Wang, Suning
, p. 1462 - 1465 (2017)
We report here a facile B(C6F5)3 catalyzed trans-aminoboration of internal alkynes, furnishing 3-position borylated indoles at ambient temperature. This reaction proceeds with the breaking of a B-N bond and the formation of N-C and B-C bonds to produce indole and derivatives in one step. It works well for various boron reagents and alkynyl-anilines. The borylated indoles can be further derivatized to give column stable organoboron compounds that can be used for future functionalization.
A cyclization-rearrangement cascade for the synthesis of structurally complex chiral gold(I)-aminocarbene complexes
Kolundzic, Filip,Murali, Annamalai,Perez-Galan, Patricia,Bauer, Jonathan O.,Strohmann, Carsten,Kumar, Kamal,Waldmann, Herbert
, p. 8122 - 8126 (2014)
A facile synthesis of chiral cyclic alkyl aminocarbene-gold(I) complexes from gold-free 1,7-enyne substrates was developed. The novel cyclization-rearrangement reaction sequence is triggered by the addition of (Me2S)AuCl to different 1,7-enynes and leads to structurally unique carbene-gold(I) complexes in high yields. These novel complexes are catalytically active and inhibit the proliferation of different human cancer cell lines.
Structurally-defined direct C-magnesiation and C-zincation of N-heterocyclic aromatic compounds using alkali-metal-mediated metallation
Conway, Ben,Hevia, Eva,Kennedy, Alan R.,Mulvey, Robert E.
, p. 2864 - 2866 (2007)
Demonstrating direct synergic "low polarity metallation", 1-methylindole is C-magnesiated by (TMEDA)2·Na 2MgBu4 and C-zincated by (TMEDA)·Na( tBu)(TMP)Zn(tBu), and 1-methylpyrrole is C-zincated by the same reagent, with all three metal products successfully crystallographically characterised. The Royal Society of Chemistry.
Reaction of Phenacyltriphenylarsonium Bromides with N-Methylaniline and N,N-Dimethylaniline
Bansal, Raj Kumar,Bhagchandani, Gope
, p. 2423 - 2424 (1980)
Reaction of phenacyltriphenylarsonium bromide with N-methylaniline furnished 2-phenylindole predominantly together with 1-methyl-2-phenylindole.The corresponding reaction of the arsonium salt with N,N-dimethylaniline did not give any indole, instead a simple nucleophilic substituted product, α-4'-(dimethylamino)deoxybenzoin was obtained.But, the latter reaction on being carried out in presence of hydrobromic acid afforded 1-methyl-2-phenylindole by the demethylation of N,N-dimethylaniline.
PALLADIUM-PHOSPHINE COMPLEX CATALYZED CROSS-COUPLING REACTION OF 1-METHYL-2-PYRROLYL-MAGNESIUM BROMIDE AND -ZINC CHLORIDE WITH ORGANIC HALIDES
Minato, Akio,Tamao, Kohei,Hayashi, Tamio,Suzuki, Keizo,Kumuda, Makoto
, p. 5319 - 5322 (1981)
1-Methyl-2-pyrrolyl-magnesium bromide and -zinc chloride, which were prepared from 1-methyl-2-pyrrolyllithium with MgBr2 and ZnCl2 respectively, reacted with aryl- and heteroaromatic halides to give the corresponding 2-substituted pyrroles in good to excellent yields in the presence of palladium-phosphine complexes as catalysts.
Regioselective Direct C2 Arylation of Indole, Benzothiophene and Benzofuran: Utilization of Reusable Pd NPs and NHC-Pd@MNPs Catalyst for C–H Activation Reaction
Hegde, Rajeev V.,Ong, Tiow-Gan,Ambre, Ram,Jadhav, Arvind H.,Patil, Siddappa A.,Dateer, Ramesh B.
, p. 1397 - 1405 (2020/10/02)
Abstract: A regioselective C2 arylation of indoles, benzothiophene and benzofuran without directing group has been accomplished using economically cheap Pd NPs and NHC-Pd@MNPs catalyst. The reusable catalyst is efficiently employed to access C2 arylated heterocycles in good to excellent yield. The reusability of the catalyst is studied up to five cycles and a gram-scale synthesis has been achieved. The reaction mechanism is well supported by control experiments and literature precedents. Grapic Abstract: [Figure not available: see fulltext.]
In Situ Preparation of Palladium Nanoparticles for C-2 Selective Arylation of Indoles in Agro-Waste Extract Based Mixed Solvents
Jin, Weiwei,Liu, Chenjiang,Liu, Tianxiang,Sun, Yajun,Wang, Bin,Wang, Rui,Xia, Yu,Zhang, Yonghong
supporting information, p. 2470 - 2473 (2021/06/25)
An efficient and practical method for the in situ generation of palladium nanoparticles was successfully established in a water extract of pomelo peel ash. The produced palladium nanoparticles were characterized by energy-dispersive X-ray spectroscopy elemental mapping, field emission scanning electron microscopy, high-resolution transmission electron microscope, X-ray powder diffraction, and showed high catalytic activity for selective C-2 arylation of indoles. A series of 2-arylindoles were smoothly installed in moderate to good yields through the direct palladium-catalyzed cross-coupling reactions of indoles and iodoarenes without external ligand, base, oxidant, and preinstallation directing group.
Discovery of New 4-Indolyl Quinazoline Derivatives as Highly Potent and Orally Bioavailable P-Glycoprotein Inhibitors
Chen, Zhe-Sheng,Dai, Qing-Qing,Li, Guo-Bo,Liu, Hong-Min,Liu, Hui,Wang, Bo,Wang, Shaomeng,Yu, Bin,Yuan, Shuo,Zhang, Jing-Ya,Zhang, Xiao-Nan,Zuo, Jia-Hui
, p. 14895 - 14911 (2021/10/12)
The major drawbacks of P-glycoprotein (P-gp) inhibitors at the clinical stage make the development of new P-gp inhibitors challenging and desirable. In this study, we reported our structure-activity relationship studies of 4-indolyl quinazoline, which led to the discovery of a highly effective and orally active P-gp inhibitor, YS-370. YS-370 effectively reversed multidrug resistance (MDR) to paclitaxel and colchicine in SW620/AD300 and HEK293T-ABCB1 cells. YS-370 bound directly to P-gp, did not alter expression or subcellular localization of P-gp in SW620/AD300 cells, but increased the intracellular accumulation of paclitaxel. Furthermore, YS-370 stimulated the P-gp ATPase activity and had moderate inhibition against CYP3A4. Significantly, oral administration of YS-370 in combination with paclitaxel achieved much stronger antitumor activity in a xenograft model bearing SW620/Ad300 cells than either drug alone. Taken together, our data demonstrate that YS-370 is a promising P-gp inhibitor capable of overcoming MDR and represents a unique scaffold for the development of new P-gp inhibitors.
Synthesis of 2-Substituted Benzothio(seleno)phenes and Indoles via Ag-Catalyzed Cyclization/Demethylation of 2-Alkynylthio(seleno)anisoles and 2-Alkynyldimethylanilines
Cai, Tao,Feng, Chengjie,Shen, Fangqi,Bian, Kejun,Wu, Chunlei,Shen, Runpu,Gao, Yuzhen
supporting information, p. 653 - 656 (2020/12/23)
An Ag-catalyzed cyclization/demethylation of 2-alkynylthio(seleno)anisoles and 2-alkynyldimethylanilines is described and applied for the construction of valuable benzothio(seleno)phenes as well as indoles. Various 2-substituted benzothio(seleno)phenes and indoles were obtained in good to excellent yields under mild reaction conditions with low catalyst loading. An application of this new method is also exemplified with a concise synthesis of a bioactive molecule precursor. Furthermore, a conceivable reaction mechanism is proposed with supports from isotope-exchange experiments.
B(C6F5)3-Catalyzed Electron Donor-Acceptor Complex-Mediated Aerobic Sulfenylation of Indoles under Visible-Light Conditions
Yuan, Wenkai,Huang, Jie,Xu, Xin,Wang, Long,Tang, Xiang-Ying
supporting information, p. 7139 - 7143 (2021/09/14)
An efficient B(C6F5)3-catalyzed aerobic oxidative C-S cross-coupling reaction of thiophenol with indoles was developed, affording a wide range of diaryl sulfides in good yields. An electron donor-acceptor complex between B(C6F5)3 and indoles was formed, facilitating the photoinduced single-electron transfer (SET) from indole substrates to the B(C6F5)3 catalyst. This protocol demonstrates a new reaction model using B(C6F5)3 as a single-electron oxidant.
