84186-26-5

Upstream product

• 2025-40-3 ethyl benzylidenecyanoacetate 
• 135-19-3 β-naphthol 
• 50897-91-1 ethyl 2-cyano-3-(4-methoxyphenyl)-acrylate 
• 100-52-7 benzaldehyde 
• 105-56-6 ethyl 2-cyanoacetate 
• 64992-15-0 C₈H₁₅N₂O₂⁽¹⁺⁾*Cl^(1-) 
• 64-17-5 ethanol 
• 1277100-30-7 C₂₅H₂₇N₂O₃⁽¹⁺⁾*Cl^(1-) 

Relevant academic research and scientific papers

Synthesis and biological evaluation of benzochromenopyrimidinones as cholinesterase inhibitors and potent antioxidant, non-hepatotoxic agents for Alzheimer's disease

We report herein the straightforward two-step synthesis and biological assessment of novel racemic benzochromenopyrimidinones as non-hepatotoxic, acetylcholinesterase inhibitors with antioxidative properties. Among them, compound 3Bb displayed a mixed-type inhibition of human acetylcholinesterase (IC50 = 1.28 ± 0.03 μM), good antioxidant activity, and also proved to be non-hepatotoxic on human HepG2 cell line.

Molecular hybridization based design and synthesis of new benzo[5,6]chromeno[2,3-b]-quinolin-13(14H)-one analogs as cholinesterase inhibitors

A Series of new tacrine analogs were designed, synthesized, characterized by respective spectral data and evaluated for cholinesterase inhibitory activity to be useful in Alzheimer’s disease. Most of the synthesized compounds showed good in vitro inhibitory activities toward acetyl cholinesterase (AChE) and butyrylcholinesterase (BuChE) enzymes. Among the compounds, 6i, 6o and 6r with increased saturated carboxylic ring size attached to the pyridine moiety and having 3,4-dihydroxy, 3,4,5-trimethoxy substituents on the aromatic ring attached at the stereogenic center have shown equal potency to that of tacrine with IC50values 0.65 ± 0.06, 1.32 ± 0.02 and 0.85 ± 0.05, 1.65 ± 0.12 and 0.92 ± 0.03, 1.91 ± 0.12 μM against AChE and BuChE, respectively. Standard drug tacrine exhibited IC50 values of 0.47 ± 0.02 and 0.65 ± 0.08, while Donepezil showed IC50 0.71 ± 0.06 and 0.31 ± 0.04 μM against AChE and BuChE, respectively. Docking studies of all the molecules disclosed close hydrogen bond interactions with the binding site.

Aqua one-pot, three-component synthesis of dihydropyrano[3,2-c]chromenes and amino-benzochromenes catalyzed by sodium malonate

The widespread biological properties of dihydropyrano[3,2-c]chromenes, 2-amino-4-aryl-4H-benzo[h]chromenes, and 3-amino-1-aryl-1H-benzo[f]chromenes have led to increasing efforts for the development of tremendously effective synthetic protocols aimed at their synthesis. In this contribution, sodium malonate was employed for the first time as an efficient catalyst for the one-pot, three-component tandem Knoevenagel–cyclocondensation reaction of 4-hydroxycoumarin (or naphthols), malononitrile/ethyl cyanoacetate, and various aldehydes. These compounds underwent Knoevenagel–Michael–Thorpe–Ziegler cyclization upon heating at 70?°C in water to give the respective medicinally relevant dihydropyrano[3,2-c]chromenes and amino-benzochromenes. The method is versatile and amenable to many substrates as it requires no specialized devices such as microwave, ultrasound and ball-milling. Also, the salient features of this high-yielding protocol are green reaction conditions, the use of commercially available catalyst, easy purification processes by a simple filtration, and relatively shorter reaction times.

Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water

A variety of 4H-chromenes, benzochromenes, 4,5-dihydropyrano[3,2-c]chromenes, 4H-pyran-3-carboxylates, and 3,4-disubstituted isoxazol-5(4H)-ones have been synthesized in high yields by using potassium hydrogen phthalate (KHP) as an inexpensive, commercially available catalyst. It was found that the three-component tandem reaction enabled synthesis of pyran-annulated heterocycles in water at 50 °C. 3,4-Disubstituted isoxazol-5(4H)-ones were synthesized by use of 10 mol% KHP in water at room temperature. Also, treatment of methylene-containing compounds (malononitrile or ethyl cyanoacetate) with aromatic aldehydes in the presence of 5 mol% KHP resulted in α,β-unsaturated nitriles. The procedure is an easily performed, straightforward method for synthesis of a variety of pyran-annulated compounds, isoxazol-5(4H)-one-containing heterocycles, and Knoevenagel adducts. The reaction is safe, uses mild conditions, and is environmentally benign. Other notable advantages are reuse of the catalyst, no use of hazardous organic solvents, and ease of work-up.

Potassium phthalimide-catalysed one-pot multi-component reaction for efficient synthesis of amino-benzochromenes in aqueous media

2-Amino-4-aryl-4H-benzo[h]chromenes and 3-amino-1-aryl-1H-benzo[f]chromenes were prepared by treating cyano-methylene compounds (malononitrile or ethyl cyanoacetate), substituted aromatic aldehydes, and naphtholic compounds in the presence of potassium phthalimide as a green, mild, efficient, and commercially available organocatalyst in aqueous media. The procedure was readily conducted and affords remarkable advantages such as safety, short reaction times, environmentally benign milder reaction conditions, no organic solvent required, and high yields.

An efficient one-pot synthesis of substituted 1h-naphtho[2,1-b]pyrans and 4h-1-benzopyrans (=Chromenes) under solvent-free microwave-irradiation conditions

A facile heterogeneous synthesis of 3-amino-1-aryl-1H-naphtho[2,1-b]pyran and 2-amino-4-aryl-4H-1-benzopyran derivatives 3 and 5, respectively, was carried out efficiently by one-pot three-component coupling of an aromatic aldehyde 1, an active methylene compound 2, and naphthalen-2-ol or a phenol 4 in the presence of 5-A molecular sieves under solvent-free microwave-irradiation conditions (Scheme 1 and 2, Tables 1 and 2). The catalyst was recovered and recycled (Table 3). Copyright

Triton B catalyzed three-component, one-pot synthesis of 2-amino-2-chromenes at ambient temperature

A one-pot, three-component synthesis of 2-amino-2-chromenes is described at ambient temperature by the reaction of an aldehyde and malononitrile or ethyl cyanoacetate with α-naphthol or β-naphthol in ethanol in presence of a catalytic amount of Triton B.

Task specific onium salt as soluble support in multicomponent synthesis of 4-aryl-2-amino-3-ethoxycarbonyl-naphthopyrans

In this paper was presented an application of task specific onium salt as soluble support in multicomponent synthesis of 2-amino-3-ethoxycarbonyl- naphthopyrans. The starting task-specific onium salt was functionalized in good yield with chloroethyl alcohol, followed by three steps containing esterification, three components reaction and cleavage from onium salt to afford naphthopyrans in 60% -88% overall yields. All of the products were characterized by IR, 1H NMR, 13C NMR and MS techniques. In this paper was presented an application of task specific onium salt as soluble support in multicomponent synthesis of 2-amino-3-ethoxycarbonyl-naphthopyrans. The starting task-specific onium salt was functionalized in good yield with chloroethyl alcohol, followed by three steps containing esterification, three components reaction and cleavage from onium salt to afford naphthopyrans in 60%-88% overall yields. All of the products were characterized by IR, 1H NMR, 13C NMR and MS techniques.

Aqueous [bmim][BF4] as green solvent in microwave-assisted organic reactions: Clean synthesis of 1H-benzo[f]chromene derivatives

The mixture of hydrophilic [bmim][BF4] and water has been found to be a green and safe reaction medium in the synthesis of ethyl 3-amino-1-aryl-1H-benzo[f]chromene derivatives using domestic microwave oven.

Studies with Polyfunctionally Substituted Heterocycles: Synthesis of New Pyridines, Naphthopyrans, Pyrazolo(3,4-b>pyridines and Pyrazolopyrimidines

A variety of new polyfunctionally substituted pyridines, naphthopyrans and pyrazolopyrimidines were prepared via reacting ylidenemalononitriles with thiophenol, thionaphthol, naphthols or aminopyrazoles. Keywords: Heterocycles, Pyridines, Pyrimidines