36926-84-8

Usage

Uses

2-AMINO-3-PHENYLQUINOLINE is a useful research chemical.

InChI:InChI=1/C15H12N2/c16-15-13(11-6-2-1-3-7-11)10-12-8-4-5-9-14(12)17-15/h1-10H,(H2,16,17)

Upstream product

• 59387-82-5 2-amino-3-phenylquinoline 1-oxide 
• 13493-47-5 N-(2-formylphenyl)acetamide 
• 141-52-6 sodium ethanolate 
• 140-29-4 phenylacetonitrile 
• 7647-01-0 hydrogenchloride 
• 136036-43-6 3-(2-nitro-phenyl)-2-phenyl-acrylonitrile 
• 5344-90-1 2-Aminobenzyl alcohol 
• 247222-84-0 2-(2-phenylethynyl)phenyl isocyanide 
• 13141-39-4 N-<2-(2-Phenylethynyl)phenyl>methanamide 
• 100-51-6 benzyl alcohol 
• 136036-43-6 (Z)-3-(2-Nitrophenyl)-2-phenylacrylsaeurenitril 

Downstream Products

• 1426925-60-1 C₅₄H₄₀N₄Si₂ 
• 113508-26-2 4-Phenyl-imidazo[1,2-a]quinoline-2-carboxylic acid 
• 113508-45-5 4-Phenyl-imidazo[1,2-a]quinoline-2-carboxylic acid ethyl ester 
• 38035-81-3 3-phenyl-quinolin-2-ol 

Relevant academic research and scientific papers

Palladium-Catalyzed Cyclization of N-Acyl- o-alkynylanilines with Isocyanides Involving a 1,3-Acyl Migration: Rapid Access to Functionalized 2-Aminoquinolines

A simple and expedient approach for the synthesis of functionalized 2-aminoquinolines via palladium-catalyzed annulation of N-acyl-o-alkynylanilines with isocyanides has been developed with high atom economy, in which an unconventional 6-endo-dig cyclization process is observed. Further investigations of the mechanism demonstrated that an intramolecular acyl migration of the N-protecting groups was involved in this transformation.

Metal-Free Synthesis of Alkenylazaarenes and 2-Aminoquinolines through Base-Mediated Aerobic Oxidative Dehydrogenation of Benzyl Alcohols

A metal-free, base-mediated, and atom-efficient oxidative dehydrogenative coupling of substituted phenylmethanols (benzyl alcohols) with methyl azaarenes or phenylacetonitriles to afford substituted alkenylazaarenes or 2-aminoquinolines, respectively is described. CsOH.H2O was discovered to be the base of choice for obtaining optimal yields of the title compounds, although the reaction could proceed with KOH as well. The protocol that works efficiently in the presence of air is amenable over broad range of substrates.

α-Alkylation of arylacetonitriles with primary alcohols catalyzed by backbone modified N-heterocyclic carbene iridium(i) complexes

A series of backbone-modified N-heterocyclic carbene (NHC) complexes of iridium(i) (1d-f) have been synthesized and characterized. The electronic properties of the NHC ligands have been assessed by comparison of the IR carbonyl stretching frequencies of thein situprepared [IrCl(CO)2(NHC)] complexes in CH2Cl2. These new complexes (1d-f), together with previously prepared1a-c, were applied as catalysts for the α-alkylation of arylacetonitriles with an equimolar amount of primary alcohols or 2-aminobenzyl alcohol. The catalytic activities of these complexes could be controlled by modifying the N-substituents and backbone of the NHC ligands. The NHC-IrIcomplex1fbearing 4-methoxybenzyl substituents on the N-atoms and 4-methoxyphenyl groups at the 4,5-positions of imidazole exhibited the highest catalytic activity in the α-alkylation of arylacetonitriles with primary alcohols. Various α-alkylated nitriles and aminoquinolines were obtained in high yields through a borrowing hydrogen pathway by using 0.1 mol%1fand a catalytic amount of KOH (5 mol%) under an air atmosphere within significantly short reaction times.

Sustainable Synthesis of Quinazoline and 2-Aminoquinoline via Dehydrogenative Coupling of 2-Aminobenzyl Alcohol and Nitrile Catalyzed by Phosphine-Free Manganese Pincer Complex

A sustainable synthesis of quinazoline and 2-aminoquinoline via acceptorless dehydrogenative annulation is presented. The reaction is catalyzed by earth-abundant well-defined manganese complexes bearing NNS ligands. Furthermore, a one-pot synthetic strate

Synthesis of Quinolines Through Acceptorless Dehydrogenative Coupling Catalyzed by Rhenium PN(H)P Complexes

A practical and sustainable synthesis of substituted quinolines was achieved through the annulation of 2-aminobenzyl alcohol with various secondary alcohols, ketones, aldehydes, or nitriles, under hydrogen-borrowing conditions. Under the catalysis of well-defined rhenium complexes bearing tridentate diphosphinoamino ligands, the reaction proceeded efficiently (31 examples were isolated with yields up to 96 %) affording a variety of quinoline derivatives.

Dehydrogenative Synthesis of Quinolines, 2-Aminoquinolines, and Quinazolines Using Singlet Diradical Ni(II)-Catalysts

Simple, straightforward, and atom economic methods for the synthesis of quinolines, 2-aminoquinolines, and quinazolines via biomimetic dehydrogenative condensation/coupling reactions, catalyzed by well-defined inexpensive and easy to prepare singlet diradical Ni(II)-catalysts featuring two antiferromagnetically coupled singlet diradical diamine type ligands are described. Various polysubstituted quinolines, 2-aminoquinolines, and quinazolines were synthesized in moderate to good yields from different low-cost and readily accessible starting materials. Several control experiments were carried out to get insight into the reaction mechanism which shows that the nickel and the coordinated diamine ligands participate in a synergistic way during the dehydrogenation of alcohols.

Azide-Triggered Bicyclization of o-Alkynylisocyanobenzenes: Synthesis of Tetrazolo[1,5-a]quinolines

An efficient and rapid synthetic approach for the synthesis of tetrazolo[1,5-a]quinolines has been developed employing the reaction of o-alkynylisocyanobenzenes with sodium azide. The present strategy involved nucleophilic addition of azide to isocyanide followed by 6-endo cyclization. The reaction gives access to a collection of tetrazolo[1,5-a]quinolines with broad functional group in moderate to high yields under metal-, and base-free conditions.

Ruthenium(II)-NNN-Pincer-Complex-Catalyzed Reactions Between Various Alcohols and Amines for Sustainable C?N and C?C Bond Formation

An air and moisture stable 2-hydroxypyridine based bifunctional ruthenium NNN-pincer complex catalyzed efficient (TON=42840) N-alkylation of amines under mild conditions. Surprisingly, with cyclic secondary amines this methodology selectively produced only amides. Notably, N-methylation of several amines was achieved by using methanol as a green methylating agent. Furthermore, with lower catalyst loading (0.2 mol%) and shorter reaction time (6 h) numerous substituted quinolines were synthesized from 2-aminobenzyl alcohols and secondary alcohols. The effectiveness of this protocol was further extended by successfully synthesizing 2-alkylaminoquinolines in a one-pot fashion from amino alcohol, aliphatic nitriles, and alcohols. Gram scale synthesis of various compounds was also investigated to demonstrate the synthetic applicability of this methodology. (Figure presented.).

Synthesis of 2-Alkylaminoquinolines and 1,8-Naphthyridines by Successive Ruthenium-Catalyzed Dehydrogenative Annulation and N-Alkylation Processes

A new one-pot synthetic protocol, enabling the facile access to 2-alkylaminoquinolines and 1,8-naphthyridines by successive ruthenium-catalyzed dehydrogenative annulation and N-alkylation processes, has been demonstrated. A series of 2-aminoarylmethanols were efficiently converted in combination with different types of nitriles and alcohols into various desired products in moderate to excellent yields after isolation. Advantageously, the synthesis proceeds with high atom-efficiency, broad substrate scope, operational simplicity, no need for external hydrogen sources and less environmentally benign halogenated reagents, thus offering a practical approach to access these two types of compounds that are currently difficult to prepare with the conventional methods. (Figure presented.).

Multifunctional catalysis of a ruthenium-grafted hydrotalcite: One-pot synthesis of quinolines from 2-aminobenzyl alcohol and various carbonyl compounds via aerobic oxidation and aldol reaction

The Ru-grafted hydrotalcite was found to be an excellent multifunctional catalyst for one-pot synthesis of quinolines from 2-aminobenzyl alcohol and various carbonyl compounds. These quinolines were obtained through aerobic oxidation by the Ru species, followed by aldol reaction on base sites of the hydrotalcite.