79140-31-1

Upstream product

• 110-91-8 morpholine 
• 634-47-9 2-chloro-4-methylquinoline 
• 64658-04-4 2-bromo-4-methyl-quinoline 
• 109-02-4 4-methyl-morpholine 
• 551-93-9 2-aminoacetophenone 
• 607-66-9 4-methylquinolin-2-ol 
• 5765-65-1 4-(benzoyloxy)morpholine 
• 4053-40-1 4-methylquinoline 1-oxide 
• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 4394-85-8 4-morpholinecarboxaldehyde 

Relevant academic research and scientific papers

Cu-Catalyzed carbamoylation: Versus amination of quinoline N -oxide with formamides

An efficient, direct carbamoylation and amination of quinoline N-oxides with formamides to access 2-carbamoyl and 2-amino quinolines has been developed through copper-catalyzed C-C and C-N bond formations via cross-dehydrogenative coupling reactions. The reaction proceeds smoothly over a broad range of substrates with excellent functional group tolerance under mild conditions. Mechanistic studies suggest that the reaction is initiated by formamide radical or decarbonylative aminyl radical formation in the presence of TBHP, according to the different substituent on the N atom of formamide.

Copper-Catalyzed Deoxygenative C-2 Amination of Quinoline N-Oxides

An unprecedented reaction between quinoline N-oxides with O-benzoylhydroxylamines was developed by using CuCl as catalyst, generating deoxygenative products of 2-aminoquinolines in good yields. 1,2-Dichloroethane (DCE) as solvent was also served as reduci

Preparation method of quinoline derivative

The invention belongs to the field of medicine synthesis, and particularly relates to a preparation method of a quinoline derivative. According to the method, cuprous salt is used for catalyzing quinoline-N-oxide; then, carbamylation or amination reaction is performed. The reaction catalyst is cheap; the quinoline-N-oxide with lower activity can be subjected to carbamylation reaction; the reactionis simple; the implementation is easy; the yield is improved; the quinoline-N-oxide and N,N-disubstituted formamide can take amination reaction; the amination reaction method of the quinoline-N-oxideis expanded.

Robust Acenaphthoimidazolylidene Palladacycles: Highly Efficient Catalysts for the Amination of N-Heteroaryl Chlorides

A series of robust N-heterocyclic carbene palladacycles have been successfully developed. These showed high catalytic activity and selectivity toward the challenging amination of N-heteroaryl chlorides. Different primary and secondary amines were fully compatible with this catalytic system. Remarkably, no double amination products could be detected when primary amines were utilized in our catalytic transformation. Furthermore, the protocol has been successfully extended to synthesize rosiglitazone, a clinical drug for diabetes mellitus, highlighting its potential pharmaceutical feasibility.

Cu-catalyzed aerobic oxidative cyclizations of 3-N-hydroxyamino-1,2-propadienes with alcohols, thiols, and amines to form α-O-, S-, and N-substituted 4-methylquinoline derivatives

A one-pot, two-step synthesis of α-O-, S-, and Nsubstituted 4-methylquinoline derivatives through Cu-catalyzed aerobic oxidations of N-hydroxyaminoallenes with alcohols, thiols, and amines is described. This reaction sequence involves an initial oxidation of N-hydroxyaminoallenes with NuH (Nu = OH, OR, NHR, and SR) to form 3-substituted 2-en-1-ones, followed by Bronsted acid catalyzed intramolecular cyclizations of the resulting products. Our mechanistic analysis suggests that the reactions proceed through a radical-type mechanism rather than a typical ni-trone-intermediate route. The utility of this new Cu-catalyzed reaction is shown by its applicability to the synthesis of several 2-amino-4-methylquinoline derivatives, which are known to be key precursors to several bioactive molecules.

Novel robust benzimidazolylidene palladium complexes: Synthesis, structure, and catalytic applications in amination of chloroarenes

A series of novel pyridine stabilized PdeNHC complexes were developed, which revealed high activities and broad substrates tolerance in the amination of various (hetero)-aryl chlorides. Besides various secondary amines, a wide range of primary anilines and aliphatic amines were also well tolerated. The results highlight us a new strategy to increase catalyst activity in the future catalyst design by alternating the σ-donor property and flexibility of NHC ligands.

6-Acylamino-2-aminoquinolines as potent melanin-concentrating hormone 1 receptor antagonists. Identification, structure-activity relationship, and investigation of binding mode

Novel 6-acylamino-2-aminoquinoline melanin-concentrating hormone 1 receptor (MCH1R) antagonists were identified by sequential in silico screening with 3D pharmacophore models derived from a series of benzamide antagonists. The structure-activity relationship exploration by synthesis of analogues found structural demands around the western part of the compounds to be quite specific, whereas much structural freedom was found in the eastern part. While these compounds in general suffered from poor solubility properties, the 4-trifluoromethoxy-phenoxyacetamide western appendage provided a favorable combination of activity and solubility properties. The amine in the eastern appendage, originally required by the pharmacophore model and believed to interact with Asp123 in transmembrane 3 of MCH1R, could be removed without diminishing affinity or functional activity of the compounds. Docking studies suggested that the Asp123 interacts preferentially with the nitrogen of the central quinoline. Synthesis and testing of specific analogues supported our revised binding mode hypothesis.

A facile method for nucleophilic aromatic substitution of cyclic amine

The expeditious solventless nucleophilic aromatic substitution using microwaves is described. A non-conventional synthetic procedure has been developed where basic alumina has been used as energy transfer medium under Microwave Irradiation (MWI). The results were compared with those obtained by the classical method. This rapid and environmentally benign method avoids the use of excess solvents and toxic bases usually employed in the process make this procedure very attractive for synthesis.

Reinvestigation of a 5H-Dibenzotriazonine Synthesis

Treatment of 5-chloro-2-aminobenzophenone (1) with o-phenylenediamine, sodium acetate, and acetic acid gave 2-(acetyl)amino-5-chlorobenzophenone (5) rather than N--1,2-benzenediamine (3), as reported by Kulkarni et al.Authentic 3 was prepared and treated with chloroacetic acid and polyphosphoric acid (PPA) to give 1, recovered 3, 2,8-dichloro-6,12-diphenyldibenzodiazocine (9) and 2-chloro-6-(chloromethyl)-13-phenyl-5H-dibenzotriazonine (10).Treatment of 5 with PPA, with or without chloroacetic acid, gave phenyl> phenylmethanone (11) as the sole product in 90percent yield.Treatment of other benzophenones, acetophenones, and anilines with sodium acetate and acetic acid provided acetanilides in 78-96percent yield, with the exception of 2'-aminoacetophenone (20), wich gave a quantitative yield of 2--4-methylquinoline (21).The mechanism of acetanilide formation with sodium acetate and acetic acid is discussed.The structure of 21 was established using high resolution 1H nmr techniques.Attempts to prepare an authentic sample of 21 from 2-chlorolepidine (26) and (20) gave 4-methyl-N--2-quinolinamine (29) as the major product.