- Carbostyril derivatives: Synthesis of novel carbostyril-3′-carbonitrilselenophene hybrid compounds and investigation of their antiproliferative properties on prostate and breast cancer
-
To synthesize a new series of carbostyril-3′-carbonitrilselenophene hybrid compounds, Pechmann coumarin compounds were reacted with 2-amino-3′-carbonitrilselenophene derivatives and their anticancer activities on MCF7 and DU145 cell lines and antioxidant activities were investigated. Anticancer and antioxidant activities of the starting compounds and their corresponding new hybrid compounds were compared. It was determined that IC50 values of hybrid compounds (3e, 3f, 3g, and 3h) on the MCF7 breast cancer cell line showed the highest cytotoxic activity with 7.99, 3.64, 7.72, and 2.74 μM values, respectively. In the case of anticancer activity on the DU145 prostate cancer cell line, compounds 3f and 3h were found to have the highest cytotoxic activity with IC50 values of 4.21 and 3.90 μM, respectively. The compound 3g is also the most radical scavenging compound with an inhibition value of 88.78%.
- Er?at?r, Mehmet,Y?ld?r?m, Metin,Giray, Elife Sultan
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p. 290 - 301
(2020/10/12)
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- Design, synthesis, and antifungal evaluation of novel coumarin-pyrrole hybrids
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A series of coumarin derivatives bearing a pyrrole scaffold were designed, prepared, and assessed for their in vitro antifungal activities against six phytopathogenic fungi. The antifungal activity screening results suggest that some synthesized hybrids exhibited potential fungicidal activities against the tested fungi. In particular, compounds 6j, 6k, 6o, 6p, and 6r displayed significant antifungal effects against Rhizoctorzia solani, and possessed EC50 values of 3.94, 7.75, 6.38, 6.25, and 7.67 μg/ mL, respectively. The above activities are more potent than the commercialized fungicide Boscalid (11.52 μg/mL) and Osthole (9.79 μg/mL). These results provide a significant reference for further rational design of coumarin-based fungicides.
- Zhang, Shuguang,Tan, Xin,Liang, Chaogen,Zhang, Weihua
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p. 450 - 458
(2020/11/30)
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- B(C6F5)3-catalyzed synthesis of coumarins via Pechmann condensation under solvent-free conditions
-
Tris(pentafluorophenyl)borane [B(C6F5)3] catalyzed simple, efficient and environmentally benign protocol has been developed for the Pechmann condensation using variety of phenols and β-ketoesters under solvent-free conditions to afford coumarin derivatives. The present protocol displayed significant advantages such as low catalyst loading, short reaction time, mild reaction conditions, low toxicity, easy work-up, high yields, and compatibility with other functional groups. In addition, it is a convenient, clean, and fast alternative approach for synthesizing variety of coumarin derivatives. Moreover, the applicability of this method towards large-scale synthesis demonstrated its suitability for the industrial application. Graphic abstract: [Figure not available: see fulltext.]
- Prajapti, Santosh Kumar,Rao, S. Prakash
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p. 469 - 473
(2021/03/26)
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- Immobilized ionic liquid on the zeolite: its characterization and catalytic activity in the synthesis of coumarins via Pechmann reaction
-
In this work, in the first step, the 1-methyl-3-(3-trimethoxysilylpropyl) imidazolium chloride ([MTMSPIm]Cl) is immobilized on HY and NaY zeolites as an acidic catalyst. The synthesized catalysts were well characterized by different methods such as FTIR, TGA, XRD, BET, SEM, EDX and ICP. The characterizations of catalysts indeed show the ionic liquid supported on amine-functionalized zeolites. Also, the result shows the micro-/mesoporous structure for catalysts which have been emerged as an important class of catalytic materials. The micro-/mesocatalyst ([MTMSPIm]Cl@zeolite) was used as an acidic catalyst to synthesize coumarins via Pechmann reaction in solvent-free condition. The effect of different factors such as catalyst amount, solvent and time was investigated. Finally, catalyst can be easily separated and reused for the next reactions at least for five runs without any significant changes in yield and structure of the catalyst. Comparison of modified zeolite with [MTMSPIm]Cl shows higher yield and selectivity and mild condition related to other works.
- Zendehdel, Mojgan,Khaghaninejad, Soheila,Tavakoli, Fatemeh,Ganji, Shiva
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p. 2555 - 2565
(2020/05/22)
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- Iron-Catalyzed Regioselective Decarboxylative Alkylation of Coumarins and Chromones with Alkyl Diacyl Peroxides
-
A facile iron-catalyzed decarboxylative radical coupling of alkyl diacyl peroxides with coumarins or chromones has been developed, affording a highly efficient approach to synthesize a variety of α-alkylated coumarins and β-alkylated chromones. The reaction proceeded smoothly without adding any ligand or additive and provided the corresponding products containing a wide scope of functional groups in moderate to excellent yields. This protocol was highlighted by its high regioselectivity, readily available starting materials, and operational simplicity.
- Jin, Can,Sun, Bin,Xu, Tengwei,Yan, Zhiyang,Zhang, Xun
-
supporting information
p. 1585 - 1591
(2019/08/07)
-
- Recyclable cellulose nanocrystal supported Palladium nanoparticles as an efficient heterogeneous catalyst for the solvent-free synthesis of coumarin derivatives via von Pechmann condensation
-
2-Amino pyrimidine nanocellulose-supported Palladium nanoparticles (CNC-AMPD-Pd) as a novel bio supported nanocatalyst was prepared and characterized by ICP-AES, FT-IR, XRD, SEM, TEM, TGA and EDX techniques. The nanocatalyst demonstrated outstanding performance in Pechmann condensation between different substituted phenols and ethyl acetoacetate to obtain coumarin derivatives in good to excellent yields. The catalyst is easily recycled and reused without loss of the catalytic activity. The combined merits of reusable catalyst and solvent-free reaction conditions make the condensation with safe operation, no leaching of pd into environment, low pollution, rapid access to products and simple workup.
- Mirosanloo, Atieh,Zareyee, Daryoush,Khalilzadeh, Mohammad A.
-
-
- Anionic SO3H-functionalized ionic liquid: An efficient and recyclable catalyst for the Pechmann reaction of phenols with ethyl acetoacetate
-
This paper has reported an anionic SO3H-functionalized ionic liquid N-methylimidazolium sulfomethylsulfonate ([Hmim][HO3SCH2SO3]) for the synthesis of coumarins by Pechmann reaction. The [Hmim][HO3SCH2SO3] is easier to prepare by one-step neutralization reaction of N-methylimidazole with methanedisulfonic acid and show high catalytic performance for Pechmann reaction. Besides, the catalyst can simply be separated from the reaction mixture and recycled ten times without noticeable loss of activity.
- Song, Dayong,Chen, Jing,Liang, Yong-Min
-
supporting information
p. 692 - 698
(2018/02/16)
-
- Thymol, and preparation method and pharmaceutical composition thereof
-
The invention discloses thymol, and a preparation method and pharmaceutical composition thereof. The preparation method comprises the steps of: conducting a condensation reaction on m-cresol and ethylacetoacetate to obtain 4,7-dimethylcoumarin, performing hydrolysis decarboxylation on the 4,7-dimethylcoumarin under conditions of a strong alkali and high temperature to obtain an organic phase C containing 5-methyl-2-(prop-1-en-2-yl)phenol, and reducing the organic phase C to obtain thymol. The preparation method of thymol disclosed by the invention is mild in conditions, does not need specialreaction equipment, and facilitates industrial production. With the preparation method, position selectivity is high, almost no position isomer is generated, the separated product is high in purity, the total yield is high and the product quality accords with current drug declaration requirements.
- -
-
Paragraph 0056; 0057; 0065; 0072; 0073; 0081; 0089
(2019/01/07)
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- A green and convenient approach for the one-pot solvent-free synthesis of coumarins and β-amino carbonyl compounds using Lewis acid grafted sulfonated carbon@titania composite
-
Abstract: This paper reports an efficient protocol for the synthesis of coumarins via Pechmann reaction, and β-amino carbonyl compounds via aza-Michael reaction using catalytic amount of solid Lewis acid catalyst, C@TiO2–SO3–SbCl2. Six different catalysts were prepared by covalent immobilization of homogeneous Lewis acids onto sulfonated carbon@titania composite derived from amorphous carbon and nano-titania. Among various catalysts tested, C@TiO2–SO3–SbCl2 showed superior catalytic activity. The catalyst could be recycled without significant loss of its catalytic activity and demonstrated versatile catalysis for a wide range of substrates. Graphical abstract: [Figure not available: see fulltext.]
- Kour, Manmeet,Paul, Satya
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p. 327 - 337
(2017/02/10)
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- Preparation of a novel, efficient, and recyclable magnetic catalyst, γ-Fe2O3@HAp-Ag nanoparticles, and a solvent- and halogen-free protocol for the synthesis of coumarin derivatives
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In this protocol, Ag supported on the hydroxyapatite-core–shell magnetic γ-Fe2O3nanoparticles (γ-Fe2O3@HAp-Ag NPs) as a novel, efficient, and magnetically recyclable catalyst is synthesized, and characterized by transmission electron microscopy (TEM), scanning electron microscopy (SEM), Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), and vibrating sample magnetometry (VSM). The use of the catalyst is described in the synthesis of coumarin derivatives by the Pechmann condensation of various phenols with β-ketoesters under solvent- and halogen-free conditions at 80?°C. This novel and inexpensive method offers advantages, such as recyclability simple experimental protocol, short reaction time, minimal work-up procedure, and excellent yields of products, together with desirable, eco-friendly, green aspects by avoiding toxic elements and solvents, and ease of recovery from the reaction mixture using an external magnet.
- Abbasi, Zahra,Rezayati, Sobhan,Bagheri, Maryam,Hajinasiri, Rahimeh
-
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- The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2: H -chromen-2-one/thione analogues
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4,7-Dimethyl-2H-chromen-2-one (1) and its novel sulfur analogue 4,7-dimethyl-2H-chromen-2-thione (2) were synthesized and fully characterized by spectroscopic methods and mass spectrometry. The crystal structure of compound 2 has been determined by X-ray diffraction methods, and it crystallizes in the monoclinic I2/m space group. The molecular skeleton lies in the crystallographic mirror plane, in agreement with the expected theoretical planarity enforced by extended π-bonding. The crystal packing of both compounds is characterized by the R22(8) motif formed by intermolecular C-H?XC (X = O and S) hydrogen-bonding interactions involving the 1-benzopyran-2-one/thione moiety, as also identified by Hirshfeld surface analysis. The vibrational properties have been studied by infrared and Raman spectroscopy complemented by quantum chemical calculations and normal coordinate analysis of the potential energy distribution. The UV-Vis spectrum is interpreted in terms of TD-DFT quantum chemical calculations, showing a clear red-shift in the HOMO-LUMO electronic transition when the chromen-2-one ring is converted into chromen-2-thione.
- Delgado Espinosa, Zuly Yuliana,Saeed, Aamer,Mahmood, Shamsul,Echeverría, Gustavo A.,Piro, Oscar E.,Erben, Mauricio F.
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p. 5770 - 5783
(2017/07/10)
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- One Photocatalyst, n Activation Modes Strategy for Cascade Catalysis: Emulating Coumarin Biosynthesis with (-)-Riboflavin
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Generating molecular complexity using a single catalyst, where the requisite activation modes are sequentially exploited as the reaction proceeds, is an attractive guiding principle in synthesis. This requires that each substrate transposition exposes a catalyst activation mode (AM) to which all preceding or future intermediates are resistant. While this concept is exemplified by MacMillan's beautiful merger of enamine and iminium ion activation, examples in other fields of contemporary catalysis remain elusive. Herein, we extend this tactic to organic photochemistry. By harnessing the two discrete photochemical activation modes of (-)-riboflavin, it is possible to sequentially induce isomerization and cyclization by energy transfer (ET) and single-electron transfer (SET) activation pathways, respectively. This catalytic approach has been utilized to emulate the coumarin biosynthesis pathway, which features a key photochemical E → Z isomerization step. Since the ensuing SET-based cyclization eliminates the need for a prefunctionalized aryl ring, this constitutes a novel disconnection of a pharmaceutically important scaffold.
- Metternich, Jan B.,Gilmour, Ryan
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p. 1040 - 1045
(2016/02/05)
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- Introduction of a new ionic liquid solid acid based on clay as an efficient, recyclable and thermally stable catalyst for organic transformations
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Ammonium hydrogen sulfate based ionic liquid immobilized on Na+-montmorillonite (AHS@MMT) was prepared via anchoring ammonium hydrogen sulfate propyltriethoxysilane onto sodium montmorillonite by covalent bonds. The synthesized catalyst was ful
- Beigbaghlou, Somayyeh Sarvi,Marjani, Katayoun,Habibi, Azizollah,Atghia, Seyyed Vahid
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p. 20306 - 20316
(2016/03/01)
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- Magnetic nanoparticles functionalized ethane sulfonic acid (MNESA): as an efficient catalyst in the synthesis of coumarin derivatives using Pechmann condensation under mild condition
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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.
- Samadizadeh, Marjaneh,Nouri, Saeed,Kiani Moghadam, Faeze
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p. 6089 - 6103
(2016/06/01)
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- One-pot synthesis of coumarine derivatives using butylenebispyridinium hydrogen sulfate as novel ionic liquid catalyst
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Pechmann condensation reaction of 3-hydroxyphenol and ethyl acetoacetate in the presence of 1,1′‐butylenebispyridinium hydrogen sulfate as an efficient, green, and recyclable catalyst produces 7-hydroxy-4-methylcoumarin in good yield under solvent-free conditions at room temperature. This catalyst has advantages such as the following: good to excellent yields, short reaction times, simplicity in operation, and easy workup procedure.
- Rezayati, Sobhan,Sheikholeslami-Farahani, Fatemeh,Rostami-Charati, Faramarz,Abad, Saeid Afshari Sharif
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p. 4097 - 4107
(2016/07/06)
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- Design, synthesis and biological evaluation of novel donepezil-coumarin hybrids as multi-target agents for the treatment of Alzheimer's disease
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Combining N-benzylpiperidine moiety of donepezil and coumarin into in a single molecule, novel hybrids with ChE and MAO-B inhibitory activity were designed and synthesized. The biological screening results indicated that most of compounds displayed potent inhibitory activity for AChE and BuChE, and clearly selective inhibition to MAO-B. Of these compounds, 5m was the most potent inhibitor for eeAChE and eqBuChE (0.87 μM and 0.93 μM, respectively), and it was also a good and balanced inhibitor to hChEs and hMAO-B (1.37 μM for hAChE; 1.98 μM for hBuChE; 2.62 μM for hMAO-B). Molecular modeling and kinetic studies revealed that 5m was a mixed-type inhibitor, which bond simultaneously to CAS, PAS and mid-gorge site of AChE, and it was also a competitive inhibitor, which occupied the active site of MAO-B. In addition, 5m showed good ability to cross the BBB and had no toxicity on SH-SY5Y neuroblastoma cells. Collectively, all these results suggested that 5m might be a promising multi-target lead candidate worthy of further pursuit.
- Xie, Sai-Sai,Lan, Jin-Shuai,Wang, Xiaobing,Wang, Zhi-Min,Jiang, Neng,Li, Fan,Wu, Jia-Jia,Wang, Jin,Kong, Ling-Yi
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p. 1528 - 1539
(2016/03/16)
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- A solvent-free synthesis of coumarins using 1,3-disulfonic acid imidazolium hydrogen sulfate as a reusable and effective ionic liquid catalyst
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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.
- Shirini, Farhad,Yahyazadeh, Asieh,Mohammadi, Kamal
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p. 6207 - 6218
(2015/08/18)
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- An efficient synthesis of coumarin derivatives using a SBA-15 supported cobalt(II) nanocatalyst
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The catalytic performance of highly active cobalt(II) supported on mesoporous SBA-15 materials for the Pechmann reaction was investigated. SBA-15 supported cobalt(II) nanocatalyst was found to be efficient and easily recoverable in the Pechmann reaction of phenols and b-ketoesters to their corresponding coumarin derivatives under solvent-free conditions. The supported cobalt catalyst could be easily recovered after reaction completion and reused twelve times with an excellent durability and without any noticeable loss in activity.
- Rajabi, Fatemeh,Feiz, Afsaneh,Luque, Rafael
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p. 1621 - 1625
(2019/11/28)
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- Sulfonated core-shell magnetic nanoparticle (Fe3O4@SiO2@PrSO3H) as a highly active and durable protonic acid catalyst; Synthesis of coumarin derivatives through pechmann reaction
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Sulfonic acid supported silica coated magnetic nanoparticles (Fe3O4@SiO2@PrSO3H), was prepared by using low cost precursors and a facile immobilization technique. The final catalyst, which was characterized by XRD, FT-IR, vibrating sample magnetometer (VSM), TEM, and TGA techniques, was found to be an efficient and environmentally benign solid acid for the Pechmann condensation of substituted phenols with ethyl acetoacetate leading to the formation of coumarin derivatives. After the reaction, the catalyst could be effortlessly separated by external magnet and reused for 22 consecutive runs, without any significant loss in catalytic efficiency. The catalytic system presented offers a reusable strategy for the efficient synthesis of coumarin, simplicity in operation, and a green reaction profile by avoiding toxic conventional catalysts and solvents. Green earth and blue sky: Herein, we wish to disclose a simple bench top procedure for the synthesis of sulfonated core-shell magnetic nanoparticles (SMNPs) (Fe3O4@SiO2@PrSO3H) and discuss its performance as a very strong solid acid in the Pechmann condensation reaction.
- Esfahani, Farhad Kabiri,Zareyee, Daryoush,Yousefi, Reza
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p. 3333 - 3337
(2015/04/16)
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- Environmentally sustainable magnetic solid sulfonic acid: An efficient and reusable catalyst for the Pechmann reaction
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Abstract An environmentally benign sulfonic acid nanocomposite based on Fe3O4@SiO2 core-shell magnetic nanoparticles, Fe3O4@SiO2@Et-PhSO3H, was prepared and the acidity and utility of the catalyst were explored for the synthesis of a diverse range of coumarin derivatives under solvent-free conditions. The catalyst shows potential for scale up in the synthesis of coumarins with high purity and was easily separated by using an external magnet. The recovered catalyst was reused in seven cycles without any significant loss of activity.
- Mobaraki, Akbar,Yasham, Shahriar,Movassagh, Barahman
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supporting information
p. 1263 - 1268
(2015/06/02)
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- Synthesis and photophysical study of novel coumarin based styryl dyes
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New organic dyes comprising phenothiazine, carbazole, indole, diphenylamine moieties, as the electron donors, and coumarin ring as the electron acceptor through ethylenic π bridge were synthesized and characterized. The reaction of different coumarin-4-acetic acids with phenothiazine-3-carbaldehyde in the presence of piperidine in methanol gives highly fluorescent styryl derivatives having cis configuration of ethylenic double bond. Under similar conditions 7-methylcoumarin-4-acetic acid was condensed with indole-3-carbaldehyde, carbazole-3-carbaldehyde, and diphenyl amine aldehyde to give different styryl derivatives with trans configuration of ethylenic double bond. Synthesized compounds were also studied for photophysical properties and show solvatochromism.
- Sanap, Anita K.,Sanap, Kailas K.,Shankarling, Ganapati S.
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p. 190 - 199
(2015/05/13)
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- Synthesis and heterogeneous catalytic activity of covalently immobilized hexamine cation as a magnetically-recoverable nanocatalyst
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Functionalized magnetic core-shell nanoparticles Fe3O4-SiO2-HMTA are prepared by co-precipitation method and characterized by SEM, TEM, FT-IR, XRD, and VSM. The particles are spherical with an average size of approximately 48 nm. The catalytic activity of these nanoparticles was tested in solvent-free synthesis of coumarin derivatives. The catalyst was readily recycled by the use of an external magnetic field and can be reused four times without significant loss of activity or mass.
- Kangari, Sahar,Yavari, Issa,Maasoumi, Bakhshali
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p. 1771 - 1779
(2015/08/06)
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- Lewis acid promoted dual bond formation: Facile synthesis of dihydrocoumarins and spiro-tetracyclic dihydrocoumarins
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Lewis acid (FeCl3) mediated dual bond (C-C and C-O) formation for synthesis of 3,4-dihydrocoumarins is presented. This method has successfully delivered a number of dihydrocoumarins containing dense functionalities on the aromatic ring. Significantly, the present method enabled achieving dihydrocoumarins with tertiary as well as quaternary carbon atoms at the benzylic position. Gratifyingly, the novel spiro-tetracyclic lactones have also been dextrously prepared using this process. the Partner Organisations 2014.
- Niharika, Pedireddi,Ramulu, Bokka Venkat,Satyanarayana, Gedu
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p. 4347 - 4360
(2014/06/23)
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- 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
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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.
- Vahabi, Vahid,Hatamjafari, Farhad
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p. 13093 - 13103
(2015/02/19)
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- Use of a highly efficient and recyclable solid-phase catalyst based on nanocrystalline titania for the pechmann condensation
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Nanocrystalline titania-based sulfonic acid was used as an efficient and reusable catalyst for the synthesis of coumarins. The clean, mild acidity condition, the quantitative yields of products, the short reaction time, and the low reaction temperature are attractive features of this method, making it suitable for heat- or acid-sensitive substrates, particularly in drug synthesis. In practice, this method affords an advantageous combination of satisfactory yields, easy product isolation and purification.
- Atghia, Seyyed Vahid,Beigbaghlou, Somayyeh Sarvi
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p. 1155 - 1159
(2015/02/05)
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- Diazabicyclo[2.2.2]octane stabilized on Fe3O4 as catalysts for synthesis of coumarin under solvent-free conditions
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Fe3O4-diazabicyclo[2.2.2]octane (Fe3O 4-DABCO) magnetic nanoparticles (MNPs) catalyst was readily prepared from inexpensive starting materials in aqueous media which catalyzed the synthesis of coumarin. FTIR spectroscopy, X-ray diffraction, transmission electron micrographs were employed to characterize the properties of the synthesized Fe3O4-DABCO MNPs. High catalytic activity and ease of recovery from the reaction mixture using external magnet, and several reuse times without significant losses in performance are additional eco-friendly attributes of this catalytic system.
- Nasseri, Mohammad Ali,Sadeghzadeh, Seyed Mohsen
-
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- Recyclable CMK-5 supported sulfonic acid as an environmentally benign catalyst for solvent-free one-pot construction of coumarin through Pechmann condensation
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Sulfonic acid modified nanostructured CMK-5 is used as an alternative to conventional acid catalysts in the von Pechmann condensation of a neat mixture of substituted phenols with ethyl acetoacetate leading to the formation of coumarin derivatives at 130 °C. In comparison, CMK-5-SO3H showed a greater activity than some other homogeneous and heterogeneous catalysts. Additionally, the catalyst is reused repeatedly for 6 reaction cycles without any evidence of loss of activity, confirming the stability of the covalent bonding of acidic centers. The methodology presented offers reusable strategy for the efficient synthesis of coumarin, simplicity in operation, and green aspects by avoiding toxic conventional catalysts and solvents.
- Zareyee, Daryoush,Serehneh, Mahshad
-
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- CuFe2O4 nanoparticles: A magnetically recoverable and reusable catalyst for the synthesis of coumarins via pechmann reaction in water
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The synthesis of coumarins by hydroxyalkylation of phenols with ethyl acetoacetate (via Pechmann reaction) is attempted using magnetically separable and reusable CuFe2O4 nanoparticles in water. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.] Copyright
- Baghbanian, Seyed Meysam,Farhang, Maryam
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p. 697 - 706
(2014/01/17)
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- Magnesium bis(trifluoromethane)sulfonimide: An efficient catalyst for the synthesis of coumarins under solvent-free conditions
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Magnesium bis(trifluoromethane)sulfonimide [Mg(NTf2) 2] is an efficient catalyst for the synthesis of coumarins via the Pechmann condensation reaction of phenols and β-ketoesters under solvent-free conditions.
- Wang, Hongshe
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p. 411 - 414
(2013/05/21)
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- A green, efficient and recyclable poly(4-vinylpyridine)-supported copper iodide catalyst for the synthesis of coumarin derivatives under solvent-free conditions
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Poly(4-vinylpyridine)-supported copper iodide is reported as a green, efficient and recyclable catalyst for the synthesis of coumarin derivatives by the Pechmann reaction under solvent-free conditions. This catalyst can be recovered by simple filtration and recycled up to eight consecutive runs without any loss of their efficiency.
- Albadi, Jalal,Shirini, Farhad,Abasi, Jafar,Armand, Nezam,Motaharizadeh, Tayebeh
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p. 407 - 411
(2013/07/05)
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- Ultrasound-assisted one-pot synthesis of substituted coumarins catalyzed by poly(4-vinylpyridinium) hydrogen sulfate as an efficient and reusable solid acid catalyst
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Poly(4-vinylpyridinium) hydrogen sulfate solid acid was found to be efficient catalyst for synthesis of substituted coumarins via Pechmann reaction using ultrasound irradiation at room temperature and neat condition in high yields with short reaction times. This methodology offers momentous improvements over various options for the synthesis of coumarins with regard to yield of products, simplicity in operation and green aspects by avoiding toxic catalysts and solvents. Further, the catalyst can be reused and recovered for several times.
- Khaligh, Nader Ghaffari
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p. 1062 - 1068
(2013/04/24)
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- An environmentally friendly, chemoselective, and efficient protocol for the preparation of coumarin derivatives by Pechman condensation reaction using new and reusable heterogeneous Lewis acid catalyst polystyrene-supported GaCl 3
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An environmentally benign Pechman protocol for the one-pot synthesis of 4-substituted coumarins through the condensation reactions of phenol substrates with β-ketoesters using polystyrene-supported GaCl3 (PS-GaCl3) as a highly active and reusable solid Lewis acid catalyst under mild and heterogeneous conditions in good to excellent yields is described. This new protocol is easy, simple, cost-effective, chemoselective, and in addition has the advantages of easy availability, stability, reusability and eco-friendly character of the catalyst, high to excellent yields, simple experimental and work-up procedure.
- Rahmatpour, Ali,Mohammadian, Sara
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p. 271 - 278
(2013/05/08)
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- Zirconium(IV)-modified silica@magnetic nanocomposites: Fabrication, characterization and application as efficient, selective and reusable nanocatalysts for Friedel-Crafts, Knoevenagel and Pechmann condensation reactions
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A highly efficient and magnetically retrievable zirconium(IV) based nanocatalyst has been synthesized by covalent grafting of 3-hydroxy-2-methyl-1, 4-naphthoquinone onto amine functionalized silica coated magnetic nanoparticles followed by complexation with ZrOCl2. The structural and magnetic properties of obtained nanocatalyst are identified by TEM, SEM, XRD, EDS, VSM and FT-IR analyses. The potential of resultant organic-inorganic hybrid nanocatalyst was effectively evaluated for the range of organic transformations such as Friedel-Crafts, Knoevenagel and Pechmann condensation reactions. The magnetically recoverable nano-hybrid catalyst presented high TON and chemoselectivity with the ease of reusability for multiple cycles without any appreciable loss in its catalytic activity.
- Sharma,Monga, Yukti,Puri, Aditi
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p. 110 - 114
(2013/05/09)
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- Synthesis of some peracetylated glucopyranosyl thiosemicarbazones of substituted 4-formylcoumarins
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Some substituted 4-formylcoumarins were prepared by oxidation of 4-corresponding formylcoumarins using SeO2. These aldehydes were converted to thiosemicarbazones by condensation reaction with tetra-O-acetyl-β-D-glucopyranosyl thiosemicarbazide usingmicrowave-assisted heating method. The synthesized compounds were characterized by FT-IR and 1H NMR, 13C NMR and mass spectral studies.
- Thanh, Nguyen Dinh,Toan, Vu Ngoc
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p. 6609 - 6611
(2013/07/26)
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- Coumarins: Facile and expeditious synthesis via keggin-type heteropolycompounds under solvent-free condition
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Different Keggin-type heteropolycompounds were used in Pechmann reaction to obtain biologically active coumarins. Effect of solvent, catalyst loading, and molar ratios of substrates was studied to introduce the best reaction condition. The optimized reaction condition was extended to Pechmann reaction of methylacetoacetate with various monohydric and polyhydric phenols. This rapid procedure afforded structurally diverse coumarins with high to excellent yields. Short reaction times, simple work-up, and mild reaction conditions were advantages of this method. The optimized catalysts were reusable for four runs.
- Rafiee, Ezzat,Fakhri, Akram,Joshaghani, Mohammad
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p. 1121 - 1128
(2013/10/21)
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- Synthesis of coumarins via Pd-catalyzed oxidative cyclocarbonylation of 2-vinylphenols
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Palladium-catalyzed oxidative cyclocarbonylation of 2-vinylphenols constitutes a simple, direct method for the synthesis of coumarins. The reaction conditions, employing low pressures of CO, and air or 1,4- benzoquinone as the oxidant, are attractive in terms of environmental considerations and operational simplicity. Coumarins with a variety of functional groups were prepared in yields up to 85%.
- Ferguson, Jamie,Zeng, Fanlong,Alper, Howard
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p. 5602 - 5605,4
(2012/12/12)
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- [HSO3-pmim][CH3SO3] catalyzed one-pot protocol for the synthesis of coumarins under solvent-free conditions
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A mild and efficient protocol for the synthesis of coumarins from different phenol and ethyl acetoacetate via Pechmann reacation using acidic ionic liquids [1-methyl-3-(3-sulfopropyl)-imidazolium methyl sulphate] as catalyst under solvent-free conditions has been developed. The advantages of this protocol are low catalyst loading, better yields, shorter reaction time and environmentally benign.
- Song,Liu,Ma,Qi
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experimental part
p. 4433 - 4435
(2012/07/14)
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- Silica supported boric tri-sulfuric anhydride as a novel and efficient catalyst for solvent-free synthesis of coumarins via Pechmann condensation
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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
- Parhami, Abolfath,Zare, Abdolkarim,Nikrooz, Marzieh,Khalafi-Nezhad, Ali,Haghighi, Saghar Mowlazadeh,Bargebid, Rahele,Moosavi-Zare, Ahmad Reza
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p. 111 - 121,11
(2020/09/02)
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- PEG-SO3H: A mild and efficient recyclable catalyst for the synthesis of coumarin derivatives
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A simple and efficient synthesis of coumarin derivatives through condensation reaction of substituted phenols and dicarbonyl compounds using PEG-SO3H as a recyclable catalyst under solvent-free conditions is described.
- Nazeruddin,Pandharpatte,Mulani
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experimental part
p. 91 - 95
(2012/04/23)
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- Zirconium(IV)-modified silica gel: Preparation, characterization and catalytic activity in the synthesis of some biologically important molecules
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Zirconium modified silica gel was prepared by the grafting method and the resulting organic-inorganic hybrid material was found to be a highly effective catalyst for the range of organic transformations such as syntheses of coumarins, quinoxalines and 2,4
- Sharma,Sharma, Chetna
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scheme or table
p. 327 - 331
(2011/09/21)
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- Thiourea dioxide promoted efficient organocatalytic one-pot synthesis of a library of novel heterocyclic compounds
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The utility of thiourea dioxide as an efficient organocatalyst for the library synthesis of novel heterocyclic compounds via one-pot multicomponent coupling reactions is disclosed. Thiourea dioxide is an inexpensive and readily accessible catalyst, resulting in better product yields as compared to the corresponding thiourea as catalyst. Thiourea dioxide is found to be insoluble in various organic solvents and therefore at the end of the reaction products can be separated by extraction with diethyl ether and the recovered catalyst can be used several times with consistent catalytic activity.
- Verma, Sanny,Kumar, Subodh,Jain, Suman L.,Sain, Bir
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scheme or table
p. 6943 - 6948
(2011/11/05)
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- NbCl5-catalyzed, solvent-free, one-pot synthesis of coumarins
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NbCl5 is found to be an efficient catalyst for the Pechmann condensation reaction of phenols and -keto ester leading to the formation of coumarin derivatives in excellent yields under solvent-free conditions. The reaction protocol is simple and environmentally friendly.
- Gao, Shu-Tao,Li, Chao,Wang, Yanen,Ma, Jing-Jun,Wang, Chun,Zhang, Jing-Wen
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experimental part
p. 1486 - 1491
(2011/06/17)
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- Pentafluorophenylammonium triflate (PFPAT): An efficient, metal-free and reusable catalyst for the von Pechmann reaction
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Pentafluorophenylammonium triflate (PFPAT) is used as an efficient catalyst in the von Pechmann condensation of phenols with β-ketoesters leading to the formation of coumarin derivatives. Short reaction times, easy and quick isolation of the products, excellent chemoselectivity, excellent yields and ease of catalyst recovery with consistent activity makes this protocol efficient and environmentally benign.
- Montazeri, Naser,Khaksar, Samad,Nazari, Akbar,Alavi, Seyedeh Soghra,Vahdat, Seyed Mohammad,Tajbakhsh, Mahmood
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experimental part
p. 450 - 452
(2011/08/03)
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- Microwave-induced one-pot synthesis of coumarins using potassium dihydrogen phosphate as a catalyst under solvent-free condition
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Potassium dihydrogen phosphate was found to be an efficient catalyst for the Pechmann condensation of phenols with ethyl acetoacetate, leading to the formation of coumarins under microwave-irradiation and solvent-free condition. This procedure offers several advantages, including the low loading of catalysts, high yields, clean reactions, short reaction time for the synthesis of coumarins.
- Niralwad, Kirti S.,Shingate, Bapurao B.,Shingare, Murlidhar S.
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experimental part
p. 486 - 489
(2011/09/16)
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- Periodic mesoporous silica chloride (PMSCl) as an efficient and recyclable catalyst for the Pechmann reaction
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Periodic mesoporous silica chloride (PMSCl) with 2D P6mm hexagonal structure which can be prepared by a simple procedure is reported to act as an efficient and recyclable catalyst for the conversion of a variety of phenols into their corresponding coumarins through Pechmann reaction. The reactions were conducted under solvent-free conditions in good to excellent yields.
- Karimi, Babak,Behzadnia, Hesam
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experimental part
p. 1432 - 1436
(2012/07/31)
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- Poly(4-vinylpyridine)-supported sulfuric acid: An efficient solid acid catalyst for the synthesis of coumarin derivatives under solvent-free conditions
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Poly(4-vinylpyridine)-supported sulfuric acid is an efficient catalyst for the Pechmann condensation of acetoacetic esters with phenols, leading to the formation of coumarins in good yields within a few minutes under solvent-free microwave conditions. The catalyst used can be recovered and reused after activation. Springer-Verlag 2011.
- Borah, Kalyan Jyoti,Borah, Ruli
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experimental part
p. 1253 - 1257
(2012/06/01)
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- On the possibility of tuning molecular edges to direct supramolecular self-assembly in coumarin derivatives through cooperative weak forces: Crystallographic and hirshfeld surface analyses
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Four organic compounds based on substituted coumarin derivatives (1 - 4) have been synthesized and characterized by X-ray structural studies with a detailed analysis of Hirshfeld surface and fingerprint plots facilitating a comparison of intermolecular interactions in building different supramole-cular architectures. The X-ray study reveals that in the molecular packing C - H · · ·O, π · · · π, and carbonyl (lone pair) · · · π interactions cooperatively take part. The recurring feature of the self-assembly in all the compounds is the appearance of the molecular ribbon through weak hydrogen bonding. These hydrogen bonded ribbons further stacked into molecular layers by π · · · π forces. The mode of cooperativity of the weak C - H · · · O and π · · · π forces is such that they operate in mutuallyperpen-dicular directions - hydrogen bonding in the plane of the molecule at their edges and π-stacking perpendicular to the molecular plane. Investigation of intermolecular interactions and crystal packing via Hirshfeld surface analyses reveals that more than two-thirds of the close contacts are associated with weak interactions. Hirshfeld surface and breakdown of the corresponding fingerprint plots of four coumarin structures clearly quantify the interactions within the crystal structures, revealing significant similarities in the interactions experienced by each compound. The binding energies associated with the weak interactions have been estimated using density functional theory calculations.
- Seth, Saikat Kumar,Sarkar, Debayan,Jana, Atish Dipankar,Kar, Tanusree
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experimental part
p. 4837 - 4849
(2012/03/27)
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- Microwave assisted one-pot synthesis of nitrogen and oxygen containing heterocycles from acyl Meldrum's acid
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One-pot syntheses of biologically active nitrogen and oxygen containing heterocyclic compounds such as uracils and thiouracils and 1,4-benzothiazines, 4-methylcoumarins and 4H-1,4- dihydropyridines, using acyl Meldrum's acids are reported.
- More,Mahulikar
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experimental part
p. 745 - 747
(2011/06/27)
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- Intermediates in the von Pechmann reaction
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Condensation of meta-aesol with ethyl acetoacetate in dehydrated phosphoric acid is slow enough to observe formation and disappearance of the intermediates viz 1,2-dihydro-4,7-dimethyl-4-(4-hydroxy-2-methylphenyl)-coumarin (3) and 1,2-dihydro-4,7-dimethyl-4-(2-hydroxy-4-methylphenyl)-coumarin (4). GCMS analyses of the reaction mixtures indicated that 4,7-dimethylcoumarin (5) was formed from 3 and 4 by elimination of meta-cresol molecule. The compounds 3 and 4 were isolated by the column chromatography. Their structures were elucidated by the spectroscopic methods but unequivocal assignment of the structure to the particular isomer was not possible. The structures were resolved by X-ray diffraction studies.
- Nowakowska,Zaleski,Kyziol
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p. 1403 - 1411
(2008/12/20)
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- MoO3/Al2O3: An efficient and reusable heterogeneous catalyst for solvent-free synthesis of coumarins via pechmann condensation
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16 wt % alumina supported MoO3 has been found to be an efficient catalyst for the synthesis of various substituted coumarins via Pechmann condensation. This method offers several advantages like high yields, facile recovery and reusability of the catalyst without loss in activity, nearly neutral and solvent free condition.
- Singhal, Sweety,Jain, Suman L.,Sain, Bir
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p. 1205 - 1211
(2008/12/20)
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