- Chitosan and functionalized graphene oxide nanocomposite as a novel and highly efficient catalyst for production of bis-coumarins under solvent-free conditions
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Chitosan and functionalized graphene oxide nanocomposite was used as efficient, sustainable, and recyclable catalyst in the production of bis-coumarins using 4-hydroxycoumarin and aromatic aldehydes under solvent-free conditions. Chitosan was first functi
- Atashrouz, Zhale,Rostami, Esmael,Zare, Abdolkarim
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p. 179 - 201
(2021/11/18)
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- Bis [hydrazinium (1+)] hexafluoridosilicate:(N2H5)2SiF6 novel hybrid crystal as an efficient, reusable and environmentally friendly heterogeneous catalyst for Knoevenagel condensation and synthesis of biscoumari
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A simple, effective, green and nontoxic protocol was used for the Knoevenagel condensation and the biscoumarin derivatives synthesis. It have demonstrated that the use of a new hybrid crystal as a heterogeneous catalyst makes it possible to obtain several
- El hajri, Fatima,Benzekri, Zakaria,Sibous, Sarra,Ouasri, Ali,Boukhris, Said,Hassikou, Amina,Rhandour, Ali,Souizi, Abdelaziz
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- Unveiling the anti-tubercular properties of biscoumarins, through biological evaluation and docking studies
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Background: Biscoumarin scaffolds are known for their promising pharmacological properties. These compounds have not been studied for their activity against tuberculosis strains. Objective: Unveil the antitubercular properties of biscoumarin scaffolds. Me
- Acharya, Poornima,Ramana,Upadhyay, Manish,Pavale, Ganesh
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- Recyclable Amberlite IR-120 Catalyzed domino reaction: Synthesis, anticancer activity and molecular docking studies of biscoumarins
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Under mild conditions, an environmentally friendly method has been developed for the synthesis of bis-coumarins by using a reasonably lesser quantity of Amberlite IR-120 through Domino Knoevenagel–Michael reaction. In which, a series of aryl aldehydes hav
- Harish, B. G.,Ismail,Shadakshari, A. J.,Sowmya, H. B. V.,Suresha Kumara, T. H.,Yamuna, A. J.
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- CAL-B accelerated novel synthetic protocols for 3,3’-arylidenebis-4-hydroxycoumarins and dimethyl ((substituted phenyl) (phenylamino)methyl) phosphonates
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Green protocols for the syntheses of 3,3′-arylidenebis-4-hydroxycoumarins and dimethyl ((substituted phenyl) (phenylamino)methyl) phosphonates have been first time developed using biocatalyst, CAL-B (lipase). These are carried at room temperature under st
- Chavan, Anusaya S.,Kharat, Arun S.,Bhosle, Manisha R.,Dhumal, Sambhaji T.,Mane, Ramrao A.
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p. 4497 - 4512
(2021/07/26)
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- Carbon-SO3H: An efficient catalyst for the synthesis of biscoumarin under ambient reaction conditions and their in silico studies
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In this article, we have established a highly promising approach for the synthesis of biscoumarins via domino Knoevenagel–Michael condensation of 4-hydroxycoumarin and aromatic aldehydes in 2:1 ratio using carbon-SO3H as a solid acid catalyst i
- Sethiya, Ayushi,Teli, Pankaj,Manhas, Anu,Agarwal, Dinesh,Soni, Jay,Sahiba, Nusrat,Jha, Prakash,Agarwal, Shikha
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supporting information
p. 2440 - 2460
(2020/07/10)
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- Porcine pancreas lipase as a green catalyst for synthesis of bis-4-hydroxy coumarins
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4-Hydroxycoumarins represents an important structural motif in life sciences molecules with remarkable biological properties. 4-Hydroxycoumarins are important precursors in the synthesis of organic compounds and critical pharmacophores in medicinal chemis
- Bavandi, Hossein,Habibi, Zohreh,Yousefi, Maryam
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- Efficient synthesis of bis-(4-hydroxycoumarin) using sulfanilic acid as recyclable catalyst in water
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A catalytic reaction between aromatic aldehydes and 4- hydroxycoumarin has been developed to form a decent range of functionalized biscoumarin skeletons in excellent yields using sulfanilic acid as reusable catalyst in aqueous media. The catalytic reactio
- SADAT-JALALI, Mozhgan,MANAFI, Mohammadreza,HOMAMI, Seyed Saied,GORJI, Banafsheh,MONZAVI, Amirhossein
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p. 473 - 480
(2020/10/06)
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- Green synthesis of bis-coumarin derivatives using Fe(SD)3 as a catalyst and investigation of their biological activities
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A convenient, practical, green, and environmentally friendly method was developed for the synthesis of biscoumarins and corresponding tetrakis products from the reaction of 4-hydroxycoumarin and various aldehydes. The bis-coumarins were synthesized in hig
- Mahmoodi, Nosrat O.,Jalalifard, Zeinab,Fathanbari, Ghanbari Pirbasti
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p. 172 - 182
(2019/07/03)
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- Anion functionalized ionic liquid from artificial sugar: A sustainable pathway for diverse bis-enol derivatives
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An artificial sugar saccharine based anion-functionalized ionic liquid [Bmim]Sac was synthesized and used for new and straightforward strategies for the construction of a diverse range of bis-enols. The advantage of this methodology is the use of a non-to
- Sharma, Himani,Srivastava, Suman
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supporting information
p. 12054 - 12058
(2019/08/07)
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- The magnetic nanostructured natural hydroxyapatite (HAP/Fe3O4 NPs): an efficient, green and recyclable nanocatalyst for the synthesis of biscoumarin derivatives under solvent-free conditions
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Abstract: The magnetic nanostructured natural hydroxyapatite (HAP/Fe3O4 NPs) as a novel magnetic nanocatalyst was synthesized and fully characterized. The excellent catalytic activity of HAP/Fe3O4 NPs was investigated in the synthesis of biscoumarin derivatives under mild, green and solvent-free conditions. A series of aromatic (bearing different functional groups), heteroaromatic and aliphatic aldehydes have been converted to biscoumarins with good to excellent isolated yields. The significant advantages offered by the present method in close agreement with green chemistry principles are: catalyst is inexpensive, non-toxic, easy handling and reusable up to six recycle runs, magnetic separation of nanostructured catalyst, simple work-up procedure, short reaction time, high yields of products and using solvent-free conditions. Graphical abstract: [Figure not available: see fulltext.].
- Akhlaghinia, Batool,Sanati, Parvin,Mohammadinezhad, Arezou,Zarei, Zeinab
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- Fe3O4@SiO2@Im-bisethylFc [HC2O4] as a novel recyclable heterogeneous nanocatalyst for synthesis of bis-coumarin derivatives
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Nanomagnetic bisethylferrocene-containing ionic liquid supported on silica-coated iron oxide (Fe3O4@SiO2@Im-bisethylFc [HC2O4]) as a novel catalyst was designed and synthesized. The described catalyst
- Teimuri-Mofrad, Reza,Tahmasebi, Shabnam,Payami, Elmira
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- BiVO4-NPs: an efficient nano-catalyst for the synthesis of biscoumarins, bis(indolyl)methanes and 3,4-dihydropyrimidin-2(1H)-ones (thiones) derivatives
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BiVO4-NPs can be used as an efficient and reusable nano-catalyst for the promotion of the synthesis of biscoumarins, bis(indolyl)methanes and 3,4-dihydropyrimidin-2(1H)-ones (thiones) derivatives. The structures of the products were characteriz
- Shirini, Farhad,Lati, Monireh Pourghasemi
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- Simple protic ionic liquid [Et3NH][HSO4] as a proficient catalyst for facile synthesis of biscoumarins
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Abstract: We have explored a number of protic ionic liquids (PILs) as a catalyst for the synthesis of biscoumarins by condensation of 4-hydroxycoumarin with an aromatic aldehyde. Methylimidazolium- and triethylammonium-based PILs were synthesized by simple neutralization reaction with protic acids. Triethylammonium hydrogen sulfate [Et3NH][HSO4] was found to be the best among the studied PILs concerning the yield of products and reaction time period. Different biscoumarin derivatives were synthesized based on 4-hydroxycoumarin and various substituted aromatic aldehydes at optimum reaction conditions. Obtained products were separated just by simple filtration. The facile method does not require additional purification for formed products. The catalyst has shown better yields along with outstanding recyclability, providing an environmental benign protocol for the synthesis of biscoumarin derivatives. Graphical Abstract: Screening of simple protic ionic liquids as a catalyst in the synthesis of biscoumarins, out of which [Et3NH][HSO4] was found to be best among the studied PILs.
- Patil, Sandip K.,Awale, Deepak V.,Vadiyar, Madagonda M.,Patil, Suryakant A.,Bhise, Sagar C.,Kolekar, Sanjay S.
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p. 5365 - 5376
(2017/09/23)
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- One-pot synthesis of biscoumarin and dihydropyrano [c]chromene derivatives in the presence of organocatalysts under solvent-free conditions
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A simple and efficient synthesis of biscoumarin and dihydropyrano[c]chromene derivatives using catalytic amounts of imidazole or isoquinoline as organocatalyst under solvent-free conditions is reported. The present procedure offers advantages such as high
- Heydari, Reza,Shahrekipour, Fahimeh
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supporting information
p. 400 - 405
(2016/10/18)
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- A clean synthesis of bis(indolyl)methane and biscoumarin derivatives using P4VPy-CuO nanoparticles as a new, efficient and heterogeneous polymeric catalyst
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P4VPy-CuO nanoparticles as a novel solid catalyst were synthesized using an ultrasound irradiation method and characterized by X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM) and Fourier Trans
- Shirini, Farhad,Fallah-Shojaei, Abdollah,Samavi, Laleh,Abedini, Masoumeh
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p. 48469 - 48478
(2016/06/09)
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- L-Tyrosine loaded nanoparticles: An efficient catalyst for the synthesis of dicoumarols and Hantzsch 1,4-dihydropyridines
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Environmentally benign l-tyrosine loaded nanoparticles are fabricated and characterized by PCS, TEM, FT-IR and AFM studies. A novel straightforward green approach was applied for the synthesis of dicoumarols and Hantzsch 1,4-dihydropyridines using this catalyst. The structures and purity of these compounds were confirmed by FT-IR and NMR (1H, 13C and DEPT). The flexible and swelling properties of the polymer coating increase l-tyrosine dispersion and its high catalytic activity in organic reactions. This journal is
- Khaskel, Anamika,Barman, Pranjit,Jana, Utpal
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p. 13366 - 13373
(2015/02/19)
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- Starch-sulfuric acid as a bio-supported and recyclable solid acid catalyst for rapid synthesis of α,α′-benzylidene bis(4-hydroxycoumarin) derivatives
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Starch-sulfuric acid-catalyzed, simple, one pot, solvent-free, environmentally benign synthesis of α,α′-benzylidene bis(4-hydroxycoumarin) derivatives has been achieved by reaction of aromatic aldehydes with 4-hydroxycoumarin. The catalyst is reusable and has remarkable activity. This procedure has several advantages including high yields, short reaction times, easy work-up, and use of an inexpensive, moderately acidic, safe catalyst.
- Rezaei, Ramin,Sheikhi, Mohammad Reza
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p. 1283 - 1292
(2015/03/04)
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- Microwave-assisted, methanesulfonic acid-catalyzed synthesis of 3,3'-(arylmethylene)bis(4-hydroxy-2H-chromen-2-ones)
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Efficient synthesis of 3,3'-(arylmethylene)bis(4-hydroxy-2H-chromen-2-ones) has been achieved by methanesulfonic acid-catalyzed, microwave-assisted reaction of 4-hydroxycoumarin and aromatic aldehydes in ethanol. The procedure has the advantages of high y
- Qi, Xan,Xue, Meng-Wei,Sun, Xiao-Jun,Zhi, Yin,Zhou, Jian-Feng
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p. 1187 - 1192
(2014/05/06)
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- Introduction of titania sulfonic acid (TiO2-SO3H) as a new, efficient, and reusable heterogenous solid acid catalyst for the synthesis of biscoumarins
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Titania sulfonic acid (TiO2-SO3H) is easily prepared by the reaction of TiO2 with neat chlorosulfonic acid and characterized using a variety of techniques, including infrared, X-ray diffraction, Brunauer-Emmett-Teller, sca
- Shirini, Farhad,Abedini, Masoumeh,Abroon Kiaroudi, Seddigheh
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p. 1279 - 1288
(2015/11/02)
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- Sulfonated rice husk ash (RHA-SO3H) as a highly efficient and reusable catalyst for the synthesis of some bis-heterocyclic compounds
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Sulfonated rice husk ash (RHA-SO3H), a newly reported solid acid catalyst, was efficiently used for the synthesis of 4,4′-(arylmethylene)- bis-(3-methyl-1-phenyl-1H-pyrazol-5-ols), 3,3′-(arylmethylene)-bis-(4- hydroxycoumarins) and bis(indolyl)
- Seddighi, Mohadeseh,Shirini, Farhad,Mamaghani, Manouchehr
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p. 24046 - 24053
(2013/11/19)
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- Sulfated titania catalyzed water mediated efficient synthesis of dicoumarols - A green approach
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An efficient, mild, and environmental friendly method has been developed for the synthesis of dicoumarols in water over Lewis and Bronsted acid catalyst sulfated titania (TiO2/SO42-). The method involves the condensation of various aromatic and aliphatic aldehydes with 4-hydroxycoumarin. It affords the corresponding product in high yield with short reaction times employing a very low loading of catalyst. The catalyst was reused several times without significant change in activity.
- Karmakar, Bikash,Nayak, Anupam,Banerji, Julie
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experimental part
p. 4343 - 4346
(2012/09/22)
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- Benzylidene-bis-(4-hydroxycoumarin) and benzopyrano-coumarin derivatives: Synthesis, 1H/13C-NMR conformational and X-ray crystal structure studies and in vitro antiviral activity evaluations
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We report on the synthesis of 4-hydroxycoumarin dimers 1-15 bearing an aryl substituent on the central linker and fused benzopyranocoumarin derivatives 16-20 and on their in vitro broad anti-DNA and RNA virus activity evaluations. The chemical identities
- Zavrsnik, Davorka,Muratovic, Samija,Makuc, Damjan,Plavec, Janez,Cetina, Mario,Nagl, Ante,De Clercq, Erik,Balzarini, Jan,Mintas, Mladen
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experimental part
p. 6023 - 6040
(2011/09/20)
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- Catalyst-free synthesis of α,α-bis(4-hydroxycoumarin-3-yl) toluene in aqueous media under microwave irradiation
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An efficient catalyst-free synthesis of α,α-bis(4- hydroxycoumarin-3-yl)toluene was performed by the reaction of 4-hydroxycoumarin with aromatic aldehydes in aqueous media under microwave irradiation. The reaction was completed in short reaction time of 8
- Gong, Gui-Xia,Zhou, Jian-Feng,An, Li-Tao,Duan, Xiu-Li,Ji, Shun-Jun
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experimental part
p. 497 - 505
(2009/06/18)
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- The Chemistry of Coumarin Derivatives Synthesis of 3-Alkyl-4-hydroxycoumarins by Reductive Fragmentation of 3,3'-Alkylidene-4,4'-dihydroxybis
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Treatment of 3,3'-alkylidene-4,4'-dihydroxybis 1 with NaBH3CN in refluxing MeOH affords 3-alkyl-4-hydroxycoumarins 2 and 4-hydroxycoumarin (3; Scheme 1).The reaction may take place via hydride trapping of alkylidenechromandiones C formed from 1 in a retro-Michael reaction.Such a retro-Michael reaction of 1 might be biologically relevant.The presence of C during the reductive fragmentation 1 --> 2 is suggested by Diels-Alder and nucleophilic trapping of the alkylidenechromandiones C as well as from cross-over experiments with coumarins other than 3 (see Scheme 2).The reductive fragmentation of 1 allows the chemo- and regioselective synthesis of a variety of 3-alkyl-4-hydroxycoumarins 2 (see Table).
- Appendino, Giovanni,Cravotto, Giancarlo,Tagliapietra, Silvia,Ferraro, Stefano,Nano, Gian Mario,Palmisano, Giovanni
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p. 1451 - 1458
(2007/10/02)
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