340811-45-2

Upstream product

• 70254-43-2 4-Hydroxy-2-quinolone 
• 555-16-8 4-nitrobenzaldehdye 
• 109-77-3 malononitrile 

Relevant academic research and scientific papers

Catalytic performance of a new Br?nsted acidic oligo(ionic liquid) in efficient synthesis of pyrano[3,2-c]quinolines and pyrano[2,3-d]pyrimidines

An acidic liquid 1,3-ionene was synthesized from co-oligomerization of epichlorohydrin and imidazole followed by subjecting the resulting light oligomer to anion exchange with concentrated sulfuric acid and subsequent sulfonylation with chlorosulfonic acid. The 1H and 13C NMR spectra of the synthesized oligo(ionic liquid) displayed significant chemical shifts on transferring the oligomer from D2O to DMSO. This observation was interpreted as resulting from a conformational change in the multicationic oligomer. Application of this oligo(ionic liquid) as both solvent and acidic promoter to the synthesis of pyrano[3,2-c]quinolines and pyrano[2,3-d]pyrimidines gave fairly high yields of the products in short reaction times. The oligo(ionic liquid) is virtually stable, as could be stored for several months at room temperature and can be easily recycled several times in the synthesis of pyrano[3,2-c]quinolines and pyrano[2,3-d]pyrimidines at 80 °C without appreciable loss of activity.

Novel tacrine-based acetylcholinesterase inhibitors as potential agents for the treatment of Alzheimer’s disease: Quinolotacrine hybrids

A new series of quinolotacrine hybrids including cyclopenta- and cyclohexa-quinolotacrine derivatives were designed, synthesized, and assessed as anti-cholinesterase (ChE) agents. The designed derivatives indicated higher inhibitory effect on the acetylcholinesterase (AChE) with IC50 values of 0.285–100?μM compared to butyrylcholinesterase (BChE) with IC50 values of > 100?μM. Of these compounds, cyclohexa-quinolotacrine hybrids displayed a little better anti-AChE activity than cyclopenta-quinolotacrine hybrids. Compound 8-amino-7-(3-hydroxyphenyl)-5,7,9,10,11,12-hexahydro-6H-pyrano[2,3-b:5,6-c'] diquinolin-6-one (6m) including 3-hydroxyphenyl and cyclohexane ring moieties exhibited the best AChE inhibitory activity with IC50 value of 0.285?μM. The kinetic and molecular docking studies indicated that compound 6m occupied both the catalytic anionic site (CAS) and peripheral anionic site (PAS) of AChE as a mixed inhibitor. Using neuroprotective assay against H2O2-induced cell death in PC12 cells, the compound 6h illustrated significant protection among the assessed compounds. In silico ADME studies estimated good drug-likeness for the designed compounds. As a result, these quinolotacrine hybrids can be very encouraging AChE inhibitors to treat Alzheimer’s disease. Graphic abstract: A novel series of quinolotacrine hybrids were designed, synthesized, and evaluated against AChE and BChE enzymes as potential agents for the treatment of AD. The hybrids showed good to significant inhibitory activity against AChE (0.285–100?μM) compared to butyrylcholinesterase (BChE) with IC50 values of > 100?μM. Among them, compound 8-amino-7-(3-hydroxyphenyl)-5,7,9,10,11,12-hexahydro-6H-pyrano[2,3-b:5,6-c′] diquinolin-6-one (6?m) bearing 3-hydroxyphenyl moiety and cyclohexane ring exhibited the highest anti-AChE activity with IC50 value of 0.285?μM. The kinetic and molecular docking studies illustrated that compound 6?m is a mixed inhibitor and binds to both the catalytic anionic site (CAS) and peripheral anionic site (PAS) of AChE.[Figure not available: see fulltext.]

A novel amphipathic low-melting complex salt: An efficient homogeneous catalyst for synthesis of pyran-annulated heterocyclic scaffolds and pyrido[2,3-d]pyrimidines

The reaction of triethyl(sulfonyl)ammonium chlorosulfonate with 1,1,3,3-tetramethylguanidine (TMG) gave a low-melting complex salt with amphipathic and acidic characters. The salt has a great tendency towards solvation of organic substrates upon slight heating, so it was employed as a homogeneous acidic and functional ionic liquid catalyst in the expedient synthesis of benzo[b]pyrans, pyrano[4,3-b]pyrans, pyrano[3,2-c]quinolones, and pyrido[2,3-d]pyrimidines. The catalytic activity of the complex salt is much better than the simple salts composing it. Spectroscopic studies and chemical analysis of the salt revealed that its empirical formula is in agreement with neutralization of TMG by two H2SO4 molecules. The HSO4 ? anions of the salt seem to form extensive H-bonding with the constituting ammonium cations and Cl?, resulting in melting point depression of the complex salt due to the melting points of pure triethylamine and TMG hydrochloride salts. Another significant feature of this solid salt is that it can preserve its composition even after several times of separation from aqueous extracts and can be handled easily without danger.

Magnetic Fe3O4-supported sulfonic acid-functionalized graphene oxide (Fe3O4@GO-naphthalene-SO3H): a novel and recyclable nanocatalyst for green one-pot synthesis of 5-oxo-dihydropyrano[3,2-c]chromenes and 2-amino-3-cyano-1,4,5,6-tetrahydropyrano[3,2-c]quinolin-5-ones

Abstract: Synthesis of a novel magnetic 1-naphthalenesulfonic acid-grafted graphene oxide (Fe3O4-GO-naphthalene-SO3H) via a three-step procedure has been described. The structure of this newly synthesized nanographene oxide was fully characterized by X-ray diffraction, energy dispersive X‐ray, vibrating sample magnetometer, scanning electron microscopy, Fourier-transform infrared, Raman spectroscopy, and thermo-gravimetric analytical techniques. The catalytic efficiency of these nanoparticles as recyclable nanocatalyst was explored in one-pot three-component reaction between aldehydes, malononitrile, and 4-hydroxyquinolin-2(1H)-one or 4-hydroxycoumarin under green conditions in water for the synthesis of 2-amino-3-cyano-1,4,5,6-tetrahydropyrano[3,2-c]quinolin-5-ones and 5-oxo-dihydropyrano[3,2-c]chromenes (coumarins) respectively. High yields of the products, low reaction times, easy preparation of the catalyst, and use of water as green solvent are the main advantages of this protocol. In addition, the catalyst can be easily separated simply by using a magnet and reused for six fresh runs without significant loss of activity. Graphical abstract: [Figure not available: see fulltext.].

Cobalt ferrite encapsulated in a zwitterionic chitosan derived shell: An efficient nano-magnetic catalyst for three-component syntheses of pyrano[3,2-c]quinolines and spiro-oxindoles

A nano-magnetic core-shell composite fabricated of a unique zwitterionic chitosan-derived coating and cobalt ferrite core was found to be a green and reusable heterogeneous catalyst for efficient synthesis of pyrano[3,2-c]quinoline and spiro-oxindole derivatives in high to excellent yields. Due to having negative charges at its outermost layer and a high magnetization, the catalyst is finely dispersed in ethanol and can be easily separated from reaction mixtures by using a simple external magnet. It is reasonably stable as can be reused several times without appreciable loss of catalytic activity.

(CTA)3[SiW12]-Li+-MMT: A novel, efficient and simple nanocatalyst for facile and one-pot access to diverse and densely functionalized 2-amino-4H-chromene derivatives via an eco-friendly multicomponent reaction in water

A simple, facile and highly efficient one-pot synthesis of a pharmaceutically interesting diverse kind of functionalized 2-amino-4H-chromene by a straightforward three-component reaction of an aromatic aldehyde, malononitrile (or ethyl cyanoacetate) and diverse enolizable C-H activated acidic compounds in the presence of a catalytic amount of (CTA)3[SiW12]-Li+-MMT is reported as a novel, environmentally friendly, reusable and promising nanocatalyst reaction in refluxing water. Based on the procedure, it was feasible to synthesize 2-amino-3-cyano-pyrano[3,2-c]chromen-5(4H)-one (4a-4y), 2-amino-3-cyano-pyrano[3,2-c]quinolin-5(4H)-one (6a-6s), 2-amino-3-cyano-7,8-dihydro-4H-chromen-5(6H)-one (8a-8u), 2-amino-3-cyano-pyrano[4,3-b]pyran-5(4H)-one (12a-12f), 2-amino-3-cyano-pyrano[3,2-c]pyridine-6(5H)-one (13a-13f), and 1H-pyrano[2,3-d]pyrimidine-2,4(3H,5H)-dione (14a-14f). The structure of the nanocatalyst was confirmed by various techniques such as IR, SEM, TGA-DTG, EDX, ICP and XRD analyses. In comparison to the conventional methods, the salient features of the present protocol are green reaction conditions, high quantitative yields, short reaction time, high atom economy, low cost, easy isolation of products, and no column chromatographic separation.

Simple, catalyst-free, one-pot procedure for the synthesis of 2-amino-3-cyano-1,4,5,6-tetrahydropyrano[3,2-c]quinolin-5-one derivatives

A one-pot, three-component reaction of 4-hydroxyquinolin-2(1H)-one, malononitrile, and various aldehydes for the synthesis of 2-amino-3-cyano-1,4,5, 6-tetrahydropyrano[3,2-c]quinolin-5-one derivatives is reported. The reaction is performed without any catalysts in a mixed solvent of water and ethanol to give products in good yields. The present method provided a clean, simple, and economical alternative for the synthesis of potential biologically active pyranoquinoline derivatives. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

A green, efficient, and rapid procedure for the synthesis of 2-amino-3-cyano-1,4,5,6-tetrahydropyrano[3,2-c]quinolin-5-one derivatives catalyzed by ammonium acetate

A green, efficient, and rapid procedure for the synthesis of 2-amino-3-cyano-1,4,5,6-tetrahydropyrano[3,2-c]quinolin-5-one derivatives has been developed by one-pot condensation of 4-hydroxyquinolin-2(1H)-one, aldehyde, and malononitrile in the presence of ammonium acetate in EtOH. This method has the advantages of operational simplicity, mild reaction conditions, short reaction time, and little environmental impact.