4979-79-7

Usage

Chemical Properties

light yellow powder

InChI:InChI=1/C15H10ClN/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-10H

Upstream product

• 5659-33-6 2-phenylquinoline 1-oxide 
• 5855-52-7 2-phenylquinolin-4-amine 
• 1144-20-3 2-phenyl-4-quinolinol 
• 4637-59-6 4-Chloroquinoline N-oxide 
• 14802-18-7 2-phenyl-1H-quinolin-4-one 
• 108-86-1 bromobenzene 
• 703-61-7 2,4-dichloroquinoline 
• 934-56-5 trimethyl(phenyl)stannane 
• 98-80-6 phenylboronic acid 
• 10026-13-8 phosphorus pentachloride 
• 10025-87-3 trichlorophosphate 
• 7647-01-0 hydrogenchloride 
• 611-35-8 4-chloroquinoline 
• 591-51-5 phenyllithium 

Downstream Products

• 110244-30-9 2-phenyl-4-piperidinoquinoline 
• 14281-59-5 NSC 19826 
• 18805-33-9 bis-(2-phenyl-[4]quinolyl)-sulfide 
• 102809-87-0 cyclohexyl-methyl-(2-phenyl-[4]quinolyl)-amine 
• 103756-90-7 N⁴,N⁴-bis-(2-hydroxy-ethyl)-1-methyl-N¹-(2-phenyl-[4]quinolyl)-butanediyldiamine 
• 103990-60-9 N,N-bis-(2-hydroxy-ethyl)-N'-(2-phenyl-[4]quinolyl)-ethylenediamine 
• 22680-62-2 4-methoxy-2-phenyl-quinoline 
• 113251-56-2 cyclohexyl-(2-phenyl-[4]quinolyl)-amine 
• 109809-45-2 N,N-dimethyl-2-phenylquinolin-4-amine 
• 102080-88-6 N,N-diethyl-2-phenylquinolin-4-amine 
• 742-29-0 N-(2-phenyl-4-quinolyl)aniline 
• 102469-76-1 N-(2-phenyl-[4]quinolyl)-o-phenylenediamine 
• 103650-17-5 N,N-bis-(2-hydroxy-ethyl)-N'-(2-phenyl-[4]quinolyl)-propanediyldiamine 
• 47546-41-8 N¹,N¹-diethyl-N⁴-(2-phenylquinolin-4-yl)pentane-1,4-diamine 

Relevant academic research and scientific papers

Modular Access to Spiro-dihydroquinolines via Scandium-Catalyzed Dearomative Annulation of Quinolines with Alkynes

The catalytic enantioselective construction of three-dimensional molecular architectures from planar aromatics such as quinolines is of great interest and importance from the viewpoint of both organic synthesis and drug discovery, but there still exist many challenges. Here, we report the scandium-catalyzed asymmetric dearomative spiro-annulation of quinolines with alkynes. This protocol offers an efficient and selective route for the synthesis of spiro-dihydroquinoline derivatives containing a quaternary carbon stereocenter with an unprotected N-H group from readily accessible quinolines and diverse alkynes, featuring high yields, high enantioselectivity, 100% atom-efficiency, and broad substrate scope. Experimental and density functional theory studies revealed that the reaction proceeded through the C-H activation of the 2-aryl substituent in a quinoline substrate by a scandium alkyl (or amido) species followed by alkyne insertion into the Sc-aryl bond and the subsequent dearomative 1,2-addition of the resulting scandium alkenyl species to the C=N unit in the quinoline moiety. This work opens a new avenue for the dearomatization of quinolines, leading to efficient and selective construction of spiro molecular architectures that were previously difficult to access by other means.

Synthesis and biological evaluation of 2-phenyl-4-aminoquinolines as potential antifungal agents

Abstract: A series of 2-phenyl-4-aminoquinolines were designed, synthesized and evaluated for their antifungal activities against three phytopathogenic fungi in vitro. All of the target compounds were fully elucidated by 1H NMR, 13C

Synthesis, in vitro and in vivo biological evaluation of novel graveolinine derivatives as potential anti-Alzheimer agents

A novel series of graveolinine derivatives were synthesized and evaluated as potential anti-Alzheimer agents. Compound 5f exhibited the best inhibitory activity for acetylcholinesterase (AChE) and had surprisingly potent inhibitory activity for butyrylcho

Direct arylation for the synthesis of 2-arylquinolines from N-methoxyquinoline-1-ium tetrafluoroborate salts and arylboronic acids

A rapid and direct arylation reaction of N-methoxyquinoline-1-ium tetrafluoroborate derivatives and arylboronic acids with high regioselectivety at room temperature was discovered. The reaction shows exceptional functional group tolerance and broad substrate scope regarding both the quinoline derivatives and the arylboronic acids.

Photoredox-mediated Minisci C-H alkylation of N-heteroarenes using boronic acids and hypervalent iodine

A photoredox-mediated Minisci C-H alkylation reaction of N-heteroarenes with alkyl boronic acids is reported. A broad range of primary and secondary alkyl groups can be efficiently incorporated into various N-heteroarenes using [Ru(bpy)3]Cl2 as photocatalyst and acetoxybenziodoxole as oxidant under mild conditions. The reaction exhibits excellent substrate scope and functional group tolerance, and offers a broadly applicable method for late-stage functionalization of complex substrates. Mechanistic experiments and computational studies suggest that an intramolecularly stabilized ortho-iodobenzoyloxy radical intermediate might play a key role in this reaction system.

Chemoselective chromium(II)-catalyzed cross-coupling reactions of dichlorinated heteroaromatics with functionalized aryl Grignard reagents

Chromium(II) chloride catalyzes the chemoselective cross-coupling reaction of dichloropyridines with a range of functionalized (hetero)aromatic Grignard reagents at room temperature. Functional groups, such as esters and acetals, are well tolerated in this transformation. Previously challenging substrates, quinolines and isoquinolines, participate in the selective Cr-catalyzed cross-coupling in cyclopentyl methyl ether (CPME) as the solvent. The effective purging of Cr salts is demonstrated by using various solid supports.

Rewiring chemistry: Algorithmic discovery and experimental validation of one-pot reactions in the network of organic chemistry

Computational algorithms are used to identify sequences of reactions that can be performed in one pot. These predictions are based on over 86 000 chemical criteria by which the putative sequences are evaluated. The "raw" algorithmic output is then validated experimentally by performing multiple two-, three-, and even four-step sequences. These sequences "rewire" synthetic pathways around popular and/or important small molecules. Copyright

Synthesis of 2,4-diarylquinolines: Nickel-catalysed ligand-free cross-couplings of 4-chloro-2-arylquinolines with arylmagnesium halides in 2-methyltetrahydrofuran

A ligand-free and room temperature protocol for the synthesis of 2,4-diarylquinolines is described. Treatment of 4-chloro-2-arylquinolines with arylmagnesium halides in the presence of a catalytic amount of nickel(II) chloride without ligands in 2-methylt

Potent DNA-directed alkylating agents: Synthesis and biological activity of phenyl N-mustard-quinoline conjugates having a urea or hydrazinecarboxamide linker

A series of N-mustard-quinoline conjugates bearing a urea or hydrazinecarboxamide linker was synthesized for antitumor evaluation. The in vitro cytotoxicity studies revealed that compounds with hydrazinecarboxamide linkers were generally more cytotoxic th

NUCLEIC ACID FLUORESCENT STAINS

The present invention provides fluorescent dye compounds and methods of using the compounds for the staining of nucleic acids. In particular, the dye compounds comprise heterocyclic molecules with hydroxy alkyl and aromatic substituents, and the dye compo