57479-31-9

Upstream product

• 95149-16-9 tris-(3-methoxy-phenyl)-bismuthane 
• 5332-24-1 3-bromoquinoline 
• 5344-90-1 2-Aminobenzyl alcohol 
• 768-70-7 1-ethynyl-3-methoxybenzene 
• 67-68-5 dimethyl sulfoxide 
• 62-53-3 aniline 
• 591-31-1 3-methoxy-benzaldehyde 
• 34784-02-6 3-bromoisoquinoline 
• 10365-98-7 3-methoxyphenylboronic acid 
• 1309444-58-3 C₁₆H₁₄O₃ 
• 529-23-7 o-aminobenzaldehyde 

Downstream Products

• 893737-06-9 3-(quinolin-3-yl)phenol 
• 107915-36-6 3-(p-hydroxyphenyl)-quinoline 
• 1100255-41-1 (R)-3-(3-methoxyphenyl)-1,2,3,4-tetrahydroquinoline 

Relevant academic research and scientific papers

[3+1+1+1] Annulation to the Pyridine Structure in Quinoline Molecules Based on DMSO as a Nonadjacent Dual-Methine Synthon: Simple Synthesis of 3-Arylquinolines from Arylaldehydes, Arylamines, and DMSO

A [3+1+1+1] annulation of arylamines, arylaldehydes, and dimethyl sulfoxide (DMSO) to the pyridine structure in quinolines using DMSO as a nonadjacent dual-methine (═CH?) synthon is disclosed. In this annulation, arylamines provide two carbon atoms and one nitrogen atom, arylaldehydes furnish one carbon atom, and DMSO provides two nonadjacent methines (═CH?) to the pyridine ring in quinoline molecules. This annulation provides a simple approach for the synthesis of 3-arylquinolines from readily available substrates in useful yields. On the basis of the control experiments and the literature, a plausible mechanism is proposed.

Advancing Base-Metal Catalysis: Development of a Screening Method for Nickel-Catalyzed Suzuki-Miyaura Reactions of Pharmaceutically Relevant Heterocycles

Interest in replacing palladium catalysts with base metals resulted in the development of a 24-reaction screening platform for identifying nickel-catalyzed Suzuki-Miyaura reaction conditions. This method was designed to be directly applicable to process s

Method for preparing 3 - arylquinoline

The invention discloses a method for preparing 3 - arylquinoline, which is carried out in an oxygen-containing atmosphere, ortho-amine arylmethanol and aryl formaldehyde in DMSO-solution system containing an alkali to obtain 3 -arylquinoline compounds. In 3 - arylquinoline compound structure prepared by the method, 2 carbon atoms are provided by DMSO, aryl groups at 3 carbon atoms and 3 positions are provided by aryl formaldehyde, and all other atoms in the quinoline compound structure are provided by raw material o-amido aryl methanol. The method for synthesizing 3 - arylquinoline has the advantages of wide raw material sources, environmental friendliness, low price and simple operation, and is beneficial to industrial production.

N-heterocyclic carbene coordinated heterogeneous Pd nanoparticles as catalysts for suzuki-miyaura coupling

Palladium nanoparticle (Pd NP) catalysts immobilized in a polymer with an N-heterocyclic carbene (NHC) moiety (PICBNHC-Pd) have been developed, wherein the NHC moiety plays dual roles as a crosslinker and a ligand to activate the Pd NPs. The presence of both Pd NPs and NHC was confirmed by STEM/EDS and SR-MAS NMR analyses, respectively. This PICB-NHC-Pd catalyst showed excellent activity in the Suzuki-Miyaura coupling reaction without leaching of Pd. Excellent results were obtained in gram-scale synthesis, and catalyst recovery/reuse experiments were completed without loss of catalyst activity.

Regioselective Synthesis of C-3-Functionalized Quinolines via Hetero-Diels-Alder Cycloaddition of Azadienes with Terminal Alkynes

A highly efficient metal and protection-free approach for the regioselective synthesis of C-3-functionalized quinolines from azadienes (in situ generated from 2-aminobenzyl alcohol) and terminal alkynes through [4 + 2] cycloaddition has been developed. An unprecedented reaction of 2-aminobenzyl alcohol with 1,3- and 1,4-diethynylbenzene provided the C-3 tolylquinolines via [4 + 2] HDA and oxidative decarboxylation. The -NH2 group directed mechanistic approach was well supported by the control experiments and deuterium-labeling studies and by isolating the azadiene intermediate. The reactivity and selectivity of unprotected azadiene in metal-free base-assisted hetero-Diels-Alder reaction is exploited to quickly assemble an important class of C-3-functionalized quinolines, which are difficult to access.

Triarylbismuthanes as threefold aryl-transfer reagents in regioselective cross-coupling reactions with bromopyridines and quinolines

Cross-coupling studies using bromopyridines and bromoquinolines with triarylbismuths as threefold coupling reagents in substoichiometric amounts under Pd-catalysed conditions are disclosed. The reactivity was high with both mono- and dibromopyridyl substrates, and mono- and bis-couplings were carried out regioselectively. A library of monoaryl and diaryl pyridines was formed in high yields. A one-pot strategy provided a simple and straightforward synthesis of both symmetrical and unsymmetrical diarylpyridines. Arylations of 2-bromo- and 3-bromoquinolines were achieved with triarylbismuth reagents. This study demonstrates that triarylbismuths may be used as threefold arylating reagents for the synthesis of aryl pyridines and quinolines through couplings with bromopyridines and bromoquinolines under Pd-catalysed conditions. Copyright

A novel Friedlander-type synthesis of 3-aryl quinolines from 3-oxo-2,3-diaryl-propionaldehydes

3-Aryl quinolines are readily synthesized by a novel Friedlaender-type reaction with 3-oxo-2,3-diaryl-propionaldehydes and 2-amino arylaldehydes. A preliminary mechanism of this novel one pot, two-step synthesis has been explored with the proofs of isolation of the enaminone intermediate and the eliminated benzoic acid in this reaction.

17BETA-HYDROXYSTEROID DEHYDROGENASE TYPE 1 INHIBITORS FOR THE TREATMENT OF HORMONE-RELATED DISEASES

The invention relates to the use of non-steroidal 17beta-hydroxysteroid dehydrogenase type 1 inhibitors for the treatment and prophylaxis of hormone-dependent, particularly estrogen-dependent, diseases.The invention further relates to suitable inhibitors and to a method for the production thereof.

Design, synthesis, and biological evaluation of (hydroxyphenyl)naphthalene and -quinoline derivatives: Potent and selective nonsteroidal inhibitors of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) for the treatment of estrogen-dependent diseases

Human 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) catalyzes the reduction of the weak estrogen estrone (E1) to the highly potent estradiol (E2). This reaction takes place in the target cell where the estrogenic effect is exerted via the estrogen receptor (ER). Estrogens, especially E2, are known to stimulate the proliferation of hormone-dependent diseases. 17β-HSD1 is overexpressed in many breast tumors. Thus, it is an attractive target for the treatment of these diseases. Ligand- and structure-based drug design led to the discovery of novel, selective, and potent inhibitors of 17β-HSD1. Phenyl-substituted bicyclic moieties were synthesized as mimics of the steroidal substrate. Computational methods were used to obtain insight into their interactions with the protein. Compound 5 turned out to be a highly potent inhibitor of 17β-HSD1 showing good selectivity (17β-HSD2, ERα and β), medium cell permeation, reasonable metabolic stability (rat hepatic microsomes), and little inhibition of hepatic CYP enzymes.