70437-00-2Relevant academic research and scientific papers
Synthesis and characterization of propeller-shaped mono- to hexacationic quinolinium-substituted benzenes
Batsyts, Sviatoslav,Hübner, Eike G.,Namyslo, Jan C.,Gjikaj, Mimoza,Schmidt, Andreas
, p. 4102 - 4114 (2019/04/30)
Diels-Alder reaction of 2-, 3- and 4-(phenylethynyl)quinolines and tetraphenylcyclopentadienone gave three regioisomeric 2,3,4,5,6-pentaphenyl-1-(quinolin-2-yl, -3-yl, and -4-yl)benzenes. Restricted rotation of the 3-yl and 4-yl substituted derivatives is observed between the central core and the substituents, resulting in propeller-shaped molecules. Likewise, 1,2-diquinolinyl-3,4,5,6-tetraphenylbenzenes with 3-yl,3-yl and 3-yl,4-yl connectivity were prepared. As evidenced by NMR spectroscopy, they form two diasteromers due to their restricted rotation. A cobalt-catalyzed [2 + 2 + 2]-cyclotrimerization of 2-(phenylethynyl)quinoline resulted in the formation of triphenyl-2,4,6- and -3,5,6-tri(quinolin-2-yl)benzenes. The same reaction was applied to 3,3′-ethyne-1,2-diyldiquinoline which formed hexa(quinolin-3-yl)benzene. N-Methylation gave the title compounds. Among those, the hexacationic hexa(N-methylquinolinio-3-yl)benzene is described. Stereochemical aspects are predominantly discussed by means of results of NMR experiments. DFT-calculations on the most stable conformations and the frontier orbital profiles of the hexacation as well as of its neutral precursor have been carried out.
Visible-light induced copper(i)-catalysed denitrogenative oxidative coupling of hydrazinylpyridines with terminal alkynes
Charpe, Vaibhav Pramod,Hande, Aniket A.,Sagadevan, Arunachalam,Hwang, Kuo Chu
supporting information, p. 4859 - 4864 (2018/11/21)
Visible light mediated copper catalysed denitrogenative oxidative coupling of 2-hydrazinopyridines with terminal alkynes to form 2-(alkyl/arylethynyl) pyridines in the presence of O2 at room temperature is reported with 42 examples. This is the first report on visible light stimulated N2 elimination by an in situ generated copper(ii) superoxo/peroxo complex. N2 and water are the only by-products. The green chemistry metrics evaluation signifies that the current method is ecofriendly and economically feasible. This method allows the green synthesis of mGluR5 receptor antagonists, 2-methyl-6-(phenylethynyl)pyridine (MPEP) and 2-((3-methoxyphenyl)ethynyl)-6-methylpyridine (M-MPEP).
Ligand- and copper-free Sonogashira and Heck couplings of (Het)aryl chlorides and bromides catalyzed by palladium nanoparticles supported on in situ generated Al(OH)3
Li, Xing,Gong, Xiaolei,Li, Zhipeng,Chang, Honghong,Gao, Wenchao,Wei, Wenlong
, p. 2475 - 2479 (2017/02/05)
The ligand- and copper-free Sonogashira reaction of (Het)aryl halides (Br and Cl) with various terminal alkynes and the Heck coupling of (Het)aryl halides (Br and Cl) with a series of olefins, catalyzed by palladium nanoparticles supported on newly generated Al(OH)3, were developed. The catalyst can be readily recovered and reused 6 times without significant loss of activity and palladium leaching.
Nano palladium supported on high-surface-area metal-organic framework MIL-101: An efficient catalyst for Sonogashira coupling of aryl and heteroaryl bromides with alkynes
Annapurna, Manne,Parsharamulu,Vishnuvardhan Reddy,Suresh,Likhar, Pravin R.,Lakshmi Kantam, Mannepalli
, p. 234 - 239 (2015/03/30)
Palladium nanoparticle-incorporated metal-organic framework MIL-101 (Pd/MIL-101) was successfully synthesized and characterized using X-ray diffraction, nitrogen physisorption, X-ray photoelectron, UV-visible and infrared spectroscopies, and transmission electron microscopy. The characterization techniques confirmed high porosity and high surface area of MIL-101 and high stability of nano-size palladium particles. Pd/MIL-101 nanocomposite was investigated for the Sonogashira cross-coupling reaction of aryl and heteroaryl bromides with various alkynes under copper-free conditions. The reusability of the catalyst was tested for up to four cycles without any significant loss in catalytic activity.
2-(Substituted ethynyl)quinoline Derivatives as mGLUr5 Antagonists
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Paragraph 0105-0106, (2014/08/06)
Provided is a 2-(substituted ethynyl)quinoline derivative having an mGluR5 antagonistic activity and pharmaceutically acceptable salts thereof. The compound of the present invention can be useful as a medicament for treating and preventing mGluR5 receptor
Pd/tetraphosphine catalytic system for Cu-free Sonogashira reaction "on water"
Zhou, Rong,Wang, Wei,Jiang, Zhi-Jie,Fu, Hai-Yan,Zheng, Xue-Li,Zhang, Chun-Chun,Chen, Hua,Li, Rui-Xiang
, p. 746 - 751 (2014/03/21)
An efficient copper-free Sonogashira coupling reaction was performed on water at 100 °C with N,N,N′,N′-tetra(diphenylphosphinomethyl) pyridine-2,6-diamine (1) as a ligand, [Pd(η3-C3H 5)Cl]2 as a catalyst precursor and K3PO 4 as a base. Both aryl and heteroaryl halides were successfully alkynylated in this system, and a high turnover number (TON) up to 860000 was obtained with a catalyst loading as low as 1 ppm.
Synthesis and biological evaluation of 2-(arylethynyl)quinoline derivatives as mGluR5 antagonists for the treatment of neuropathic pain
Son, Myung-Hee,Kim, Ji Young,Lim, Eun Jeong,Baek, Du-Jong,Choi, Kihang,Lee, Jae Kyun,Pae, Ae Nim,Min, Sun-Joon,Cho, Yong Seo
supporting information, p. 1472 - 1476 (2013/03/28)
We described here the synthesis and biological evaluation of mGluR5 antagonists containing a quinoline ring structure. Using intracellular calcium mobilization assay (FDSS assay), we identified compound 5n, showing high inhibitory activity against mGluR5. In addition, it was found that compound 5n has excellent stability profile. Finally, this compound exhibited favorable analgesic effects in spinal nerve ligation model of neuropathic pain, which is comparable to gabapentin.
Functionalisation of heteroaromatic N-oxides using organic superbase catalyst
Araki, Yuta,Kobayashi, Koji,Yonemoto, Misato,Kondo, Yoshinori
supporting information; experimental part, p. 78 - 80 (2011/02/23)
Functionalisation of quinoline N-oxide was investigated using phophazene base as a catalyst; alkynylation and heteroarylation at 2-position were successfully achieved via nucleophilic addition-elimination process.
Nitrogen heteroaromatic cations by [2+2+2] cycloaddition
Cikova, Martina,Kolivoska, Viliam,Cisarova, Ivana,Saman, David,Pospisil, Lubomir,Teply, Filip
supporting information; experimental part, p. 450 - 462 (2011/02/28)
A modular approach to the construction of monocationic quaternary N-heteroaromatic frameworks was developed capitalizing on a direct pyridine-type nitrogen quaternization followed by metal-catalyzed [2+2+2] cycloaddition with gaseous acetylene. The flexib
Regiochemistry in cobalt-mediated intermolecular Pauson-Khand reactions of unsymmetrical internal heteroaromatic alkynes with norbornene
Moulton, Benjamin E.,Whitwood, Adrian C.,Duhme-Klair, Anne K.,Lynam, Jason M.,Fairlamb, Ian J. S.
experimental part, p. 5320 - 5334 (2011/08/06)
The intermolecular Pauson-Khand (PK) reactions of sterically comparable (2-phenylethynyl)heteroaromatic compounds with norbornene, mediated by Co 2(CO)8 to give cyclopentenone products, were examined in this study. A synthetic protocol utilizing focused-microwave dielectric heating proved indispensable in the efficient synthesis of the PK cyclopentenone products. "π-Deficient" heteroaromatic substrates, e.g., 2-pyrones, and some "π-excessive" heteroaromatics such as 2- and 3-thiophene and 2-furan favor the β-position in the newly formed cyclopentenone ring. Other π-excessive heteroaromatics such as 2-pyrrole or 2-indole favor the α-position. A π-excessive 3-indole derivative gave a nearly equal mixture of regioisomers. The position of the nitrogen in pyridyl-containing alkyne substrates also affects the regiochemical outcome of the PK reaction. A 2-pyridyl alkyne, possessing a proximal nitrogen, influences the regioselectivity relative to a 4-pyridyl variant quite dramatically, favoring the β-position in the newly formed cyclopentenone ring. A 2-pyrimidylalkyne exhibits similar behavior to the 2-pyridylalkyne. Compounds that do not participate in PK reactions with norbornene include (2-phenylethynyl)imidazoles and the related benzimidazoles, which promote rapid decomposition of the in situ generated (μ2-alkyne)Co2(CO)6 complexes. This stands in contrast with other nitrogen-containing heteroaromatics, e.g., pyrrole-, indole-, and pyrimidine-derived compounds, which effectively undergo PK reactions. Overall, the type of heteroaromatic group dramatically influences PK regioselectivity, which can in part be explained by rationalization of the current reaction mechanism, but not fully.
