25816-60-8Relevant academic research and scientific papers
Synthesis, and Fluorescence Properties of Coumarin and Benzocoumarin Derivatives Conjugated Pyrimidine Scaffolds for Biological Imaging Applications
Al-Masoudi, Najim A.,Al-Salihi, Niran J.,Marich, Yossra A.,Markus, Timo
, p. 1847 - 1854 (2015)
Series of coumarin and 5,6-benzomcomarin substituted pyrimidine derivatives 11-15 and 22-25 were synthesized, aiming to develop new imaging fluorescent agents. Analogously, treatment of 4-chloropyrimidine analog 16 with coumarin 3-carbohyrazide 5 under MWI condition followed by boiling with NH4OAc in HOAc furnished coumarin-1,2,4-triazolo-pyrimidine analog 18. The fluorescence property was investigated spectrophotometrically in MeOH with Rhodamine 6G as standard dye. All the compounds showed emission in the region between 331 and 495 nm. The quantum yield of all the compounds were found to be weak, except methyl benzocoumarin 3-carboxylate 22 which showed (ΦF = 0.98) in comparison to Rhodamine 6G as standard (ΦF = 0.95).
3-carboxylic acid and formyl-derived coumarins as photoinitiators in photo-oxidation or photo-reduction processes for photopolymerization upon visible light: Photocomposite synthesis and 3d printing applications
Dumur, Frédéric,Gigmes, Didier,Graff, Bernadette,Hamieh, Tayssir,Lalevée, Jacques,Noirbent, Guillaume,Rahal, Mahmoud,Toufaily, Joumana
, (2021/06/16)
In this paper, nine organic compounds based on the coumarin scaffold and different substituents were synthesized and used as high-performance photoinitiators for free radical pho-topolymerization (FRP) of meth(acrylate) functions under visible light irradiation using LED at 405 nm. In fact, these compounds showed a very high initiation capacity and very good polymerization profiles (both high rate of polymerization (Rp) and final conversion (FC)) using two and three-component photoinitiating systems based on coum/iodonium salt (0.1%/1% w/w) and coum/iodonium salt/amine (0.1%/1%/1% w/w/w), respectively. To demonstrate the efficiency of the initiation of photopolymerization, several techniques were used to study the photophysical and photochemical properties of coumarins, such as: UV-visible absorption spectroscopy, steady-state photolysis, real-time FTIR, and cyclic voltammetry. On the other hand, these compounds were also tested in direct laser write experiments (3D printing). The synthesis of photocomposites based on glass fiber or carbon fiber using an LED conveyor at 385 nm (0.7 W/cm2 ) was also examined.
Supramolecular synthesis of coumarin derivatives catalyzed by a coordination-assembled cage in aqueous solution
Li, Shao-Chuan,Cai, Li-Xuan,Zhou, Li-Peng,Guo, Fang,Sun, Qing-Fu
, p. 713 - 718 (2019/03/27)
A self-assembled Pd4L2 cage is employed as a water-soluble molecular flask for the synthesis of functionalized coumarins from a series of salicylaldehyde derivatives and cyanoacetates/malononitrile. The catalytic reaction features mild aqueous conditions and broad substrate scope. Crystal structures of the host-guest complexes for two substrates and one analogous intermediate have been obtained, shedding light on the supramolecular reaction mechanism. Michaelis-Menten kinetic studies were performed in one typical case, revealing that the rate of product formation has been enhanced by over 23-fold in contrast to the background reaction without cage. Moreover, the same reaction catalyzed by a smaller Pd6L4 cage gives a mixture of products and much lower yields, suggesting that fine-tuning on the size and symmetry of the cages’ cavity is crucial for their applications in supramolecular catalysis.
Novel nano-titania embedded on graphite (nano-TiO2@Cg) as an efficient, eco-friendly, and recyclable catalyst for one-pot, solvent-free synthesis of 4-aryl-3,4-dihydroquinolin-2(1H)-ones, 3-methyl-4-aryl/alkyl-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-ones, and coumarin-3-carboxylic esters
Nikoofar, Kobra,Molaei Yielzoleh, Fatemeh
, p. 7353 - 7367 (2018/08/29)
Abstract: A novel acid catalyst has been synthesized by commercial anatase phase nano-TiO2 and graphite (nano-TiO2@Cg) via a simple procedure and characterized by Fourier transform infrared spectroscopy, energy-dispersive X-ray spectroscopy, thermogravimetric analysis, field emission scanning electron microscopy, and potentiometric titration techniques. It has been utilized as a convenient nano-catalyst to accelerate the one-pot, solvent-free, three-component reaction of Meldrum’s acid, aromatic amines (5-methylpyrazol-3-amine), and various aromatic aldehydes to form 4-aryl-3,4-dihydroquinolin-2-(1H)-ones and 3-methyl-4-aryl/alkyl-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-ones, respectively. The catalytic activity has also examined for the preparation of coumarin-3-carboxylic esters from Meldrum’s acid, salicylaldehydes, and alcohols successfully. Low catalyst loading, clean process without utilizing any hazardous solvent, easy workup procedure, reusability and recyclability of the nano-catalyst within four runs without activity loss, high yields of the products, in addition with utilizing a vast range of substrates are some highlighted points of the reported protocols. Graphical abstract: [Figure not available: see fulltext.]
Coumarin-3-carboxylic acid ester derivative preparation method
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Paragraph 0206-0210, (2017/02/02)
The invention discloses a preparation method for a coumarin-3-carboxylic ester derivative shown as the formula (I) or the formula (II) in the specification. The method comprises the step that under the existence of FeCl3 being used as a catalyst, salicylaldehyde derivative shown as the formula (III) in the specification and 2-hydroxy-1-naphthaldehyde shown as the formula (IV) in the specification are in contact reaction with alcohol and meldrum's acid which have a general formula, namely R2OH. Through the fact that the salicylaldehyde derivative, the 2-hydroxy-1-naphthaldehyde, the alcohol or the meldrum's acid is catalyzed by FeCl3 in multi-component contact reaction under a relatively temperate condition, the coumarin-3-carboxylic ester derivative with relatively high productivity is synthesized in relatively short reaction time, and the method is simple in step, efficient and environment-friendly, and completely meets the concept of green chemistry.
Synthesis, fluorescence properties, and antiproliferative potential of several 3-oxo-3H-benzo[f]chromene-2-carboxylic acid derivatives
Fu, Xiao-Bo,Wang, Xian-Fu,Chen, Jia-Nian,Wu, De-Wen,Li, Ting,Shen, Xing-Can,Qin, Jiang-Ke
, p. 18565 - 18584 (2015/11/11)
In this study, two series of 3-oxo-3H-benzo[f]chromene-2-carboxylic acid derivatives (compounds 5a-i and 6a-g) were synthesized. Their in vitro proliferation inhibitory activities against the A549 and NCI-H460 human non-small cell lung cancer (NSCLC) cell lines were evaluated. Their photophysical properties were measured. Among these target compounds, 5e exhibited the strongest antiproliferative activity by inducing apoptosis, arresting cell cycle, and elevating intracellular reactive oxygen species (ROS) level, suggesting that it may be a potent antitumor agent. In addition, compound 6g with very low cytotoxicity, demonstrated excellent fluorescence properties, which could be used as an effective fluorescence probe for biological imaging.
Synthesis of coumarin-3-carboxylic esters via FeCl3-catalyzed multicomponent reaction of salicylaldehydes, Meldrum's acid and alcohols
He, Xinwei,Shang, Yongjia,Zhou, Yao,Yu, Zhiyu,Han, Guang,Jin, Wenjing,Chen, Jiaojiao
, p. 863 - 868 (2015/01/30)
A FeCl3-catalyzed multicomponent reaction was developed for the facile synthesis of coumarin-3-carboxylic ester derivatives in a highly atom-economic and environmentally friendly way. Using simple and cheaply available salicylaldehydes, Meldrum's acid and alcohols as the starting materials, the method needs no extra additives and features wide substrate scope, good functional group tolerance and mild reaction conditions.
Knoevenagel reaction in [MMIm][MSO4]: Synthesis of coumarins
Verdia, Pedro,Santamarta, Francisco,Tojo, Emilia
experimental part, p. 4379 - 4388 (2011/08/06)
The ionic liquid 1,3-dimethylimidazolium methyl sulfate, [MMIm][MSO 4], together with a small amount of water (the amount taken up by the ionic liquid upon exposure to air), acts efficiently as both solvent and catalyst of the Knoevenagel condensation reactions of malononitrile with 4-substituted benzaldehydes, without the need for any other solvent or promoter, affording yields of 92%-99% within 2-7 min at room temperature. When L-proline is used as an additional promoter to obtain coumarins from o- hydroxybenzaldehydes, the reaction also proceeds in high yields. Work-up is very simple and the ionic liquid can be reused several times. Some of the coumarins obtained are described for the first time.
Microwave assisted synthesis of coumarins via potassium carbonate catalyzed knoevenagel condensation in 1-n-butyl-3-methylimidazolium bromide ionic liquid
Valizadeh, Hassan,Shockravi, Abbas,Gholipur
, p. 867 - 870 (2008/04/12)
(Chemical Equation Presented) A variety of substituted coumarins have been prepared via an inexpensive and efficient potassium carbonate catalyzed Knoevenagel condensation of salisylaldehydes with acidic methylene compounds in ionic liquid media. 1-n-Butyl-3-methylimidazolium bromide has been employed as an alternative reaction medium in this procedure. The reaction proceeds smoothly under mild and solvent-free conditions and the products are obtained in excellent yields. Mild reaction conditions and good to excellent yields of the products are the noteworthy advantages of the method.
Solvent free synthesis of coumarins
Shockravi, Abbas,Shargi, Hashem,Valizadeh, Hassan,Heravi, Majid M.
, p. 2555 - 2559 (2007/10/03)
An efficient synthesis of 3-substituted coumarins under solventless system is described.
