75786-75-3

Upstream product

• 68747-34-2 (6,7-dimethyl-2-oxo-2H-chromen-4-yl)-acetic acid 
• 95-65-8 3,4-Dimethylphenol 
• 141-97-9 ethyl acetoacetate 
• 105-45-3 acetoacetic acid methyl ester 
• 201230-82-2 carbon monoxide 
• 1415385-81-7 4, 5-dimethyl-2-(prop-1-en-2-yl)phenol 

Downstream Products

• 35786-94-8 4,5-dimethyl-2-(1-methylethyl)phenol 
• 1415385-81-7 4, 5-dimethyl-2-(prop-1-en-2-yl)phenol 
• 102346-13-4 6,6'-dimethylinulavosin 

Relevant academic research and scientific papers

Linear Coumarinacenes Beyond Benzo[g]coumarins: Synthesis and Promising Characteristics

New heteroacenes, named coumarinacenes, have been designed, synthesized and characterized. They possess visible absorption and orange-red emission that are far beyond those of benzo[g]coumarins. They exhibit deep HOMO energy levels, and reveal excellent thermal, photochemical and air stabilities as compared to tetracene/pentacene. Their preliminary thin-film devices display encouraging transistor characteristics, moderate mobility and considerable environmental stability paving way into electronics.

Preparation of a novel, efficient, and recyclable magnetic catalyst, Cu(II)-OHPC-Fe3O4 nanoparticles, and a solvent-free protocol for the synthesis of coumarin derivatives

Cu(II) supported on 5-oxo-4,5-dihydro-pyrrole-3-carboxylic acid functionalized Fe3O4 nanoparticles (Cu(II)-OHPC-Fe3O4) as a new magnetic nanocatalyst was prepared and characterized by ICP-AES, FT-IR, XRD, SEM, TEM, TGA, XRD, VSM and EDX techniques. Prepared nanocatalyst (Cu(II)-OHPC-Fe3O4) is employed for Pechmann reactions between different substituted phenols and ethyl acetoacetate to obtain new products of coumarin derivatives in good to excellent yields. This green catalyst was easily removed, reused several times with no significant loss of its activity and provided clean synthesis with excellent yield and reduced time.

Magnetic nanoparticles functionalized ethane sulfonic acid (MNESA): as an efficient catalyst in the synthesis of coumarin derivatives using Pechmann condensation under mild condition

This paper reports an efficient heterogeneous catalyst based on sulfonic acid functionalization of magnetic nanoparticles. This new catalyst was prepared using the reaction between magnetic nanoparticles and sodium 2-bromoethane-1-sulfonate. Magnetic nanoparticles functionalized ethane sulfonic acid (MNESA) was found as efficient catalyst for the synthesis of coumarin derivatives using Pechmann condensation under mild condition. This reaction was catalyzed by MNESA under solvent-free condition at 90?°C, to give the corresponding products in excellent yields. The catalyst is easily separated from the reaction condition and can be reused for several times with consistence in the activity.

A solvent-free synthesis of coumarins using 1,3-disulfonic acid imidazolium hydrogen sulfate as a reusable and effective ionic liquid catalyst

Abstract 1,3-Disulfonic acid imidazolium hydrogen sulfate has been used as an effective and reusable ionic liquid catalyst for the synthesis of coumarins from phenol derivatives with β-ketoesters via the Von Pechmann condensation under solvent-free conditions. This method consistently has the advantages of excellent yields, easy and quick isolation of the products, short reaction times, and green aspects by avoiding toxic catalysts and solvents. Further, the catalyst can be recovered and reused for four times without loss of activity.

Cp?Co(III)-Catalyzed Annulations of 2-Alkenylphenols with CO: Mild Access to Coumarin Derivatives

Cp?Co(III)-catalyzed annulations of 2-alkenylphenols with CO for the synthesis of coumarin derivatives have been developed. The reaction features mild reaction conditions, broad substrate scope, and good functional group tolerance. Preliminary mechanistic studies were conducted, suggesting that C-H activation is the turnover limiting step. Furthermore, the efficiency of this reaction was demonstrated by the rapid total synthesis of three natural products herniarin, xanthyletin, and seselin.

Microwave assisted convenient one-pot synthesis of coumarin derivatives via Pechmann condensation catalyzed by FeF3 under solvent-free conditions and antimicrobial activities of the products

A rapid and efficient solvent-free one-pot synthesis of coumarin derivatives by Pechmann condensation reactions of phenols with ethyl acetoacetate using FeF3 as a catalyst under microwave irradiation is described. This one-pot synthesis on a solid inorganic support provides the products in good yields. The newly synthesized compounds were systematically characterized by IR, 1H-NMR, 13C-NMR, MS and elemental CHN analyses. The proposed solvent-free microwave irradiation method using the environmentally friendly catalyst FeF3 offers the unique advantages of high yields, shorter reaction times, easy and quick isolation of the products, excellent chemoselectivity, and a one-pot, green synthesis. The products were screened for antimicrobial activity, and the results showed that the compounds reacted against all the tested bacteria.

Silica supported boric tri-sulfuric anhydride as a novel and efficient catalyst for solvent-free synthesis of coumarins via Pechmann condensation

It is found that silica supported boric trisulfuric anhydride (BTSA.SiO2) is a novel, suitable and versatile catalyst for efficient and clean synthesis of coumarins via Pechmann cyclocondensation under mild and solvent-free conditions. Different kinds of

Al2O3/MeSO3H (AMA) as a novel heterogeneous system for synthesis of coumarins under mild conditions

Al2O3/MeSO3H (AMA) is found to be an efficient reagent for the Pechman condensation reaction of phenols and β- ketoesters under solvent free conditions. The reaction protocol is simple, cost- effective, solvent free and gives good isolated yield with high purity and good regioselectivity.

A solvent-free synthesis of coumarins using a Wells-Dawson heteropolyacid as catalyst

Seventeen examples are resolved, most of them in good to excellent yields, using the cheap WD catalyst. Substituted coumarins are synthesized from phenols and β-ketoesters by the Pechmann reaction, using a Wells-Dawson heteropolyacid (H6P2W18O62? 24H2O) as catalyst by a solvent-free procedure. This one requires low reaction times, 130°C temperature and as little as 1 mol % of Wells-Dawson acid, obtaining good to excellent yields of coumarins. The catalyst showed to be reusable with no differences in the yields. The results are compared with those of the reactions performed in toluene solution. The presented synthetic procedure is a convenient, clean and fast alternative for synthesizing 4-substituted coumarins (17 examples).

Further studies of orientation effects in the Pechmann synthesis of coumarins

A study of orientation effects in the Pechmann synthesis with some meta-substituted phenols is presented. Variation of the reaction conditions with malic acid indicates that whilst the proportion of 5-chlorocoumarin diminishes at higher temperatures that of 5-methoxycoumarin increases, accompanied by cleavage of the ether function under certain conditions. Reactions with ethyl acetoacetate give only the 4,7-isomers. Peri-substituent effects in 1 H and 13C NMR spectroscopy have been used for product identification.