15936-02-4Relevant academic research and scientific papers
Synthesis and SAR comparison of regioisomeric aryl naphthyridines as potent mGlu5 receptor antagonists
Galatsis, Paul,Yamagata, Koji,Wendt, John A.,Connolly, Cleo J.,Mickelson, John W.,Milbank, Jared B.J.,Bove, Susan E.,Knauer, Christopher S.,Brooker, Rachel M.,Augelli-Szafran, Corinne E.,Schwarz, Roy D.,Kinsora, Jack J.,Kilgore, Kenneth S.
, p. 6525 - 6528 (2007)
We describe three novel regioisomeric series of aryl naphthyridine analogs, which are potent antagonists of the Class III GPCR mGlu5 receptor. The synthesis and in vitro and in vivo pharmacological activities of these analogs are discussed.
Catalytic activity in transfer hydrogenation using ruthenium (II) carbonyl complexes containing two 1,8-naphthyridine as N-monodentate ligands
Gajardo, Juana,Araya, Juan C.,Ibá?ez, Andrés,Guerchais, Véronique,Le Bozec, Hubert,Moya, Sergio A.,Aguirre, Pedro
, p. 129 - 134 (2019)
A new series of novel complexes of type cis-[Ru(CO)2Cl2(L)2], L = 2-phenyl-1,8-naphthyridine, 2-(4′-nitrophenyl)-1,8-naphthyridine, 2-(4′-bromophenyl)-1,8-naphthyridine, 2-(4′-methylphenyl)-1,8-naphthyridine, 2-(3′-methoxyphenyl)-1,8-naphthyridine, 2-(2′-methoxyphenyl)-1,8-naphthyridine and 2-(4′-methoxyphenyl)-1,8-naphthyridine have been successfully synthesized and characterized. We found that the complexes can be directly synthesized from [RuCl2(CO)2]2 with high yield. The crystallographic structures of complex cis-[RuCl2(CO)2(2-(4′-methoxyphenyl)-1,8-naphthyridine-κN8)2] and cis-[RuCl2(CO)2(2-(2′-methoxyphenyl)-1,8-naphthyridine-κN8)2] have been established by X-ray single crystal diffraction studies, which indicate an octahedral geometry with two 1,8-naphthyridine ligands coordinated to the metal in a N-monodentate fashion. The ruthenium(II) complexes have been studied as catalysts in the transfer hydrogenation of acetophenone. We found that complexes show moderate activities and a 100% selectivity. The best turnover frequency (390 h?1) is found for cis-[RuCl2(CO)2(2-(4′-methoxyphenyl)-1,8-naphthyridine-κN8)2] when the substrate/catalysis ratio was 1000/1. The catalytic conditions were optimized using different substrate/catalyst and base/catalyst ratios.
Synthesis, characterization and structure of tribromo(2-phenyl-1,8- naphthyridine)gold(III)
Schmidt, Ricardo,Moya, Sergio A.,Aguirre, Pedro,Fuentealba, Mauricio,Leboschka, Markus,Sieger, Monika,Niemeyer, Mark,Kaim, Wolfgang
, p. 677 - 680 (2011)
Neutral tribromo(2-phenyl-1,8-naphthyridine)gold(III), AuBr 3(N-N), has been prepared by reaction of KAuBr4 with the ligand in CHCl3/C2H5OH and was characterized by 1H NMR spectroscopy and
Hydrogen-Transfer-Mediated Direct β-Alkylation of Aryl-1,8-naphthyridines with Alcohols under Transition Metal Catalyst Free Conditions
Xiong, Biao,Zhang, Shudi,Jiang, Huanfeng,Zhang, Min
, p. 724 - 727 (2016)
By employing abundant and sustainable alcohols as the alkylating reagents, a new and direct alkylation method has been demonstrated. This method enables the selective alkylation of the less substituted pyridyl ring at the β-site of aryl-1,8-naphthyridines
DIRECT SYNTHESIS OF DISUBSTITUTED AROMATIC POLYIMINE CHELATES
Dietrich-Buchecker, C. O.,Marnot, P. A.,Sauvage, J. P.
, p. 5291 - 5294 (1982)
The reaction of an alkyl- or aryl-lithium with 1,10-phenanthroline followed by hydrolysis and rearomatisation with manganese dioxide gives good yields of the 2,9-disubstituted product.This synthetic method has been extended to other polyimines such as 2,2'-bipyridine, 2,2',6',2''-terpyridine and 1,8-naphtyridine.
Mild and efficient copper-catalyzed oxidative cyclization of oximes with 2-aminobenzyl alcohols at room temperature: synthesis of polysubstituted quinolines
Liu, Yan-Yun,Wei, Yang,Huang, Zhi-Hui,Liu, Yilin
supporting information, p. 659 - 666 (2021/02/06)
A simple and efficient ligand-free Cu-catalyzed protocol for the synthesis of polysubstituted quinolinesviaoxidative cyclization of oxime acetates with 2-aminobenzyl alcohols at room temperature has been developed. The presented approach provides a new synthetic pathway leading to polysubstituted quinolines with good functional group tolerance under mild conditions. Moreover, this transformation can be applied for the preparation of quinolines on a gram scale. Oxime acetates serve as the internal oxidants in the reactions, thus making this method very attractive.
Visible-Light-Mediated Oxidative Cyclization of 2-Aminobenzyl Alcohols and Secondary Alcohols Enabled by an Organic Photocatalyst
Xu, Jing-Xiu,Pan, Nan-Lian,Chen, Jia-Xi,Zhao, Jin-Wu
, p. 10747 - 10754 (2021/08/16)
This paper describes a visible-light-mediated oxidative cyclization of 2-aminobenzyl alcohols and secondary alcohols to produce quinolines at room temperature. This photocatalytic method employed anthraquinone as an organic small-molecule catalyst and DMSO as an oxidant. According to this present procedure, a series of quinolines were prepared in satisfactory yields.
Iron-Catalyzed Amination of Strong Aliphatic C(sp3)-H Bonds
Das, Sandip Kumar,Roy, Satyajit,Khatua, Hillol,Chattopadhyay, Buddhadeb
, p. 16211 - 16217 (2020/10/26)
A concept for intramolecular denitrogenative C(sp3)-H amination of 1,2,3,4-tetrazoles bearing unactivated primary, secondary, and tertiary C-H bonds is discovered. This catalytic amination follows an unprecedented metalloradical activation mechanism. The utility of the method is showcased with the short synthesis of a bioactive molecule. Moreover, an initial effort has been embarked on for the enantioselective C(sp3)-H amination through the catalyst design. Collectively, this study underlines the development of C(sp3)-H bond functionalization chemistry that should find wide application in the context of drug discovery and natural product synthesis.
Organometal-Free Arylation and Arylation/Trifluoroacetylation of Quinolines by Their Reaction with CF3-ynones and Base-Induced Rearrangement
Muzalevskiy, Vasiliy M.,Belyaeva, Kseniya V.,Trofimov, Boris A.,Nenajdenko, Valentine G.
, p. 9993 - 10006 (2020/09/09)
The reaction of quinolines with CF3-ynones resulted in the formation of 1,3-oxazinoquinolines. Subsequent treatment of the reaction mixture with a base initiated deep structural transformation of primary products. Both steps proceed in very high yield. As a result, unusual rearrangement of 1,3-oxazinoquinolines to form either 2-arylquinolines or 2-aryl-3-trifluoroacetylquinolines was discovered. The decisive role of the base in the reaction direction was shown. Using these reactions, highly efficient pathways to 2-arylquinolines and 2-aryl-3-trifluoroacetylquinolines were elaborated to provide the corresponding compounds in high yields using a simple one-pot procedure. The possible mechanism of rearrangement is discussed.
Green phosphorescent compound and organic electroluminescent device using same
-
, (2020/04/17)
The invention discloses a green phosphorescent compound and an organic electroluminescent device using the same. The green phosphorescent compound comprises an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode which are sequentially deposited; the green phosphorescent compound represented by the following formula (I) is used as a dopant in a light-emitting layer, wherein in the formula (I), R1, R2, R3, R4, R5, R6, R7 and R8 are independently selected from hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfenyl, sulfinyl, sulfonyl, phosphino and combinations thereof; X1-X9 are selected from carbon or nitrogen; X is selected from substituted or unsubstituted naphthyridine; Y is selected from substituted or unsubstituted benzene, pyridine, pyrimidine, pyrazine and pyridazine; and n is selected from 0, 1 or 2.
