- Photophysical study of 6-amino-3-methyl-4-(4-nitrophenyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile and estimation of ground-state and singlet excited-state dipole moments by solvatochromic approaches
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An investigation of absorption and fluorescence behaviour of 6-amino-3-methyl-4-(4-nitrophenyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile (NDPPC) at room temperature was carried out using a series of twelve organic solvents with different polarities. Ground and excited state dipole moments were determined experimentally by using Lippert–Mataga polarity function, Bakhshiev solvent polarity parameter, Kawski-Chamma-Viallet solvent polarity parameter, Reichardt's microscopic solvent polarity parameter, Kamlet-Abboud-Taft multiple linear regression and Catalan dipolar polarizibility approach. Due to considerable π- electron density redistribution, the value of excited state dipole moment was found to be greater than that of the ground state. The ground state dipole moment value was determined by quantum chemical method which was used to estimate excited state dipole moment using solvatochromic correlations. Both non-specific solute-solvent interactions and hydrogen bonding interactions were investigated by using Kamlet-Abboud-Taft and Catalan method. TD-DFT (B3LYP/6-311G (d,p)) was used for the determination of HOMO-LUMO energies.
- Kumari, Rekha,Varghese, Anitha,George, Louis,K.B., Akshaya
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Read Online
- Supported palladium oxide nanoparticles in Al-SBA-15 as an efficient and reusable catalyst for the synthesis of pyranopyrazole and benzylpyrazolyl coumarin derivatives via multicomponent reactions
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An eco-friendly method for diversity-oriented synthesis of substituted dihydropyrano[2,3-c]pyrazole and benzylpyrazolyl coumarin derivatives has been achieved via one-pot and multicomponent reaction in the presence of PdO/Al-SBA-15 as an efficient and rec
- Heravi, Majid M.,Malakooti, Reihaneh,Kafshdarzadeh, Kosar,Amiri, Zahra,Zadsirjan, Vahideh,Atashin, Hassan
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p. 203 - 234
(2022/01/19)
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- Nano cobalt ferrite encapsulated-silica particles bearing melamine as an easily recyclable catalyst for the synthesis of dihydropyrano[2,3-c]pyrazoles under green conditions
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In this research, it was displayed an efficient method for synthesis of 6-amino-2,4-dihydropyrano[2,3-c] pyrazol-5-carbonitrile derivatives by using CoFe2O4 silica supported bearing melamine as a magnetic nanocatalyst. This nanocompo
- Dadaei, Mahla,Naeimi, Hossein
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- Tungstic acid (H4WO5) immobilized on magnetic-based zirconium amino acid metal–organic framework: An efficient heterogeneous Br?nsted acid catalyst for l-(4-phenyl)-2,4-dihydropyrano[2,3c]pyrazole derivatives preparation
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A new magnetic nanocatalyst based on the immobilization of tungstic acid onto new design robust, cost-effective, green, and scalable zirconium-L-aspartate amino acid metal–organic framework (MOF)-grafted L-(+)-tartaric acid stabilized magnetite nanopartic
- Khademi, Shima,Zahmatkesh, Saeed,Aghili, Alireza,Badri, Rashid
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- Concentrated solar radiation-assisted one-pot/multicomponent synthesis of pyranopyrazole derivatives under neat condition
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Concentrated solar radiation (CSR)-assisted synthesis of pyranopyrazole derivatives under solvent and catalyst-free condition has been reported in the present protocol. One-pot multicomponent synthesis from aromatic/heteroaldehyde, ethyl acetoacetate, malononitrile, and hydrazine hydrate leads to the final desired compounds in a good yield. This operationally simple methodology has several advantages such as green and clean reaction profile, simple workup and purification procedures, extremely short reaction time, atom efficiency, and being economical. The current energy-efficient method saves almost 98% of energy as compared to the conventional method. Graphical abstract: [Figure not available: see fulltext.]
- Gadkari, Yatin U.,Hatvate, Navnath T.,Telvekar, Vikas N.
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p. 4245 - 4255
(2021/07/17)
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- Sugarcane Bagasse Ash-Based Silica-Supported Boric Acid (SBA-SiO2-H3BO3): A Versatile and Reusable Catalyst for the Synthesis of 1,4Dihydropyrano[2,3c]pyrazole Derivatives
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Abstract: A simple, green, and efficient protocol has been developed for the synthesis of biologically active 1,4dihydropyrano[2,3c]pyrazole derivatives via one-pot four-component reaction of various substituted benzaldehydes, hydrazine hydrate or phenylh
- Kumar, A.,Pandey, A. K.,Shrivastava, S. C.
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p. 653 - 660
(2021/06/02)
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- Synthesis and characterization of pine-cone derived carbon-based solid acid: A green and recoverable catalyst for the synthesis of pyra-no_pyrazole, amino-benzochromene, amidoalkyl naphthol and thiazoli-dinedione derivatives
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In this report, SO3H-functionalized Carbon nanoparticles (Pine-SO3H) with high acid density have been synthesized by the thermal treatment of sulfuric acid with Pine-Cone as carbon-based at 180oC in a sealed autoclave in a
- Ghorbani, Fatemeh,Pourmousavi, Seied Ali,Kiyani, Hamzeh
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- One-pot synthesis of 2-amino-3-cyano-4H-pyrans and pyran-annulated heterocycles using sodium citrate as an organo-salt based catalyst in aqueous ethanol
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Sodium citrate as a highly efficient catalyst is developed for the synthesis of functionalized 2-amino-3-cyano-4H-pyrans and pyran-annulated heterocycles. This method involves a one-pot three-component reaction of aromatic aldehydes, malononitrile and 1,3
- Dutta, Arup,Nongkhlaw, Rishanlang,Phanrang, Pynskhemborlang T.,Thongni, Aiborlang
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supporting information
(2021/11/09)
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- Novel biocompatible core/shell Fe3O4?NFC?Co(ii) as a new catalyst in a multicomponent reaction: An efficient and sustainable methodology and novel reusable material for one-pot synthesis of 4: H -pyran and pyranopyrazole in aqueous media
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Today, due to the developing need for inexpensive catalysts, recyclable magnetic nanocatalysts immobilized on polysaccharides possess many advantages over classical heterogeneous catalysts. However, cellulose has been an appealing material in catalysis sc
- Bagherzade, Ghodsieh,Eshghi, Hossein,Kargar, Pouya Ghamari
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p. 37086 - 37097
(2020/10/27)
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- An expedient and eco-friendly approach for multicomponent synthesis of dihydropyrano[2,3-c]pyrazoles using nano-Al2O3/BF3/Fe3O4 as reusable catalyst
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The pyranopyrazole derivatives have many biological activities. They were synthesized via a four-component coupling of aromatic aldehyde, malononitrile, ethyl acetoacetate and hydrazine hydrate. In this study, dihydropyrano[2,3-c]pyrazoles have been synth
- Babaei, Elaheh,Mirjalili, Bi Bi Fatemeh
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- Green synthesis of pyrazolopyranopyrimidinone and pyranopyrazole derivatives using porphyrin-initiated amine-functionalized PolyBCMO dendritic polymer as sonocatalyst
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A novel porphyrin-initiated amine-functionalized poly-3,3-bis(chloromethyl)oxetane (PBCMO-amine) dendritic polymer was effectively synthesized. Characterization using the UV-vis, IR, NMR, PXRD, TG, and FE-SEM spectroscopy and microscopy enabled one to ass
- Avudaiappan, Govindan,Unnimaya T., Jayaprakash,Asha, Pallikkattil,Unnikrishnan, Vettukattil,Sreekumar, Krishnapillai
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p. 197 - 209
(2019/12/24)
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- Nano silica extracted from horsetail plant as a natural silica support for the synthesis of H3PW12O40 immobilized on aminated magnetic nanoparticles (Fe3O4@SiO2-EP-NH-HPA): a novel and effi
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Abstract: In this work, nanomesoporous silica has been prepared from horsetail (Equisetum arvense), which is a medicinal plant, with high surface area. This natural silica has been applied as a support to prepare H3PW12O40
- Hosseini Mohtasham, Nina,Gholizadeh, Mostafa
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p. 3037 - 3066
(2020/04/17)
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- Catalyst-free green synthesis of dihydropyrano[2,3-c]pyrazole scaffolds assisted by ethylene glycol (E-G) as a reusable and biodegradable solvent medium
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Abstract: We revealed a catalyst-free, green and rapid one-pot four-component tandem strategy for the preparation of dihydropyrano[2,3-c]pyrazoles – a biologically significant scaffold – via Knoevenagel-Michael cyclocondensation based on green chemistry p
- Mohamadpour, Farzaneh
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- DABA MNPs: A new and efficient magnetic bifunctional nanocatalyst for the green synthesis of biologically active pyrano[2,3-: C] pyrazole and benzylpyrazolyl coumarin derivatives
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In this work, a new core-shell magnetic silica nanocatalyst functionalized with 3,4-diaminobenzoic acid (Fe3O4@SiO2@PTS-DABA) was successfully prepared and characterized using different spectroscopic methods or techniques including FT-IR, FE-SEM, VSM, XRD
- Karami, Shahriar,Dekamin, Mohammad G.,Valiey, Ehsan,Shakib, Peyman
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p. 13952 - 13961
(2020/09/03)
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- Green synthesis of pyranopyrazoles via biocatalytic one-pot Knoevenagel condensation–Michael-type addition–heterocyclization cascade in non-aqueous media
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Abstract: An efficient, green and facile route for the one-pot four-component synthesis of pyranopyrazole derivatives through the condensation of the aromatic aldehydes, ethyl acetoacetate, malononitrile and hydrazine hydrate using baker’s yeast as biocat
- Pandey, Rajat,Pratap, Umesh,Shrivas, Prabhakar,Wankhade, Atul,Zodape, Sangesh
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- An inorganic–organic hybrid material based on a Keggin-type polyoxometalate@Dysprosium as an effective and green catalyst in the synthesis of 2-amino-4H-chromenes via multicomponent reactions
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A novel inorganic–organic hybrid, [Dy4(PDA)4(H2O)11(SiMo12O40)]·7H2O denoted as (POM@Dy-PDA), based on a lanthanide cluster, a Keggin-type polyoxomolybdate, and PDA (1,10-phenant
- Hosseinzadeh-Baghan, Sara,Mirzaei, Masoud,Eshtiagh-Hosseini, Hossein,Zadsirjan, Vahideh,Heravi, Majid M.,Mague, Joel T.
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- Novel task-specific ionic liquid [Et2NH(CH2)2CO2H][AcO] as a robust catalyst for the efficient synthesis of some pyran-annulated scaffolds under solvent-free conditions
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A novel task-specific ionic liquid, 2-carboxy-N,N-diethylethanaminium acetate denoted as [Et2NH(CH2)2CO2H][AcO], is prepared in an easy process and fully characterized by using suitable methods such as FT-IR, 1H-NMR, 13C-NMR, and TG, DTG and DTA analyses. After preparation, the promoting ability of this catalyst for one-pot multicomponent synthesis of 2-amino-4H-chromenes, dihydropyrano[3,2-c]chromenes and dihydropyrano[2,3-c]pyrazoles using in situ-developed arylidenemalononitriles through Knoevenagel reaction under solvent-free conditions is described. The sustainable procedure, short reaction times (6–36?min), effortless work-up, non-chromatographic purification, good-to-excellent product yields (79–96%), ease of recovery and reusability of the catalyst up to six reaction runs without a decrease of activity are the notable features of the present protocol.
- Shaikh, Mohd Akmal,Farooqui, Mazahar,Abed, Syed
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p. 1595 - 1617
(2019/01/04)
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- A highly efficient and reusable catalyst for the synthesis of 4H-benzo[b]pyran derivatives
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A series of substituted 4H-pyrans derivatives were synthesized by a one-pot, multi-component reaction of aromatic aldehydes, malononitrile, and pyrazolone derivatives or active methylene carbonyl compounds such as dimedone, in the presence of 1,3-dimethyl
- Redouane, Mohamed Abdenour,Khiri-Meribout, Naima,Benzerka, Saida,Debache, Abdelmadjid
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p. 167 - 179
(2020/02/27)
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- MIL-53(Fe) Metal–Organic Frameworks (MOFs) as an Efficient and Reusable Catalyst for the One-Pot Four-Component Synthesis of Pyrano[2,3-c]-pyrazoles
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A novel and simple approach for the efficient and rapid synthesis of pyrano[2,3-c]-pyrazoleshas been accomplished via the four-component condensation reaction of malononitrile, hydrazine hydrate, ethyl acetoacetate, and substituted aldehydes using MIL-53(
- Ghasemzadeh, Mohammad Ali,Mirhosseini-Eshkevari, Boshra,Abdollahi-Basir, Mohammad Hossein
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- Natural Phosphate K09 as a New Reusable Catalyst for the Synthesis of Dihydropyrano[2,3-c]Pyrazole Derivatives at Room Temperature
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Abstract: In this study, we report a simple, efficient and green protocol for the synthesis of pyrano[2,3-c]pyrazole derivatives by the use of the natural phosphate K09 as a mild and efficient heterogeneous catalyst. The catalytic efficiency of K09 was compared with other heterogeneous catalysts to determine the best catalyst for said conversion. Easy recovery of the catalyst and its reusability, room temperature reaction conditions, short reaction time, excellent yields, are some of the important features of this protocol.
- El Mejdoubi,Sallek,Digua,Chaair,Oudadesse
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p. 536 - 542
(2019/09/04)
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- Design and development of a new functionalized cellulose-based magnetic nanocomposite: preparation, characterization, and catalytic application in the synthesis of diverse pyrano[2,3-c]pyrazole derivatives
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In this work, a facile protocol for the preparation of a new cellulose-based functionalized magnetic nanocomposite catalyst is described. The structure and morphology of the prepared nanomaterial was characterized by scanning electron microscopy, energy-d
- Maleki, Ali,Eskandarpour, Vahid
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p. 1459 - 1472
(2019/06/10)
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- Preparation and characterization of Fe3O4@Cu-β-CD as a hybrid magnetic catalyst for the synthesis of dihydropyrano[2,3-c]pyrazoles in H2O
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Abstract: Fe3O4@Cu-β-CD is a hybrid composite with high catalytic activity. Easy separation with an external magnet and recyclability are the advantages of this catalyst. The magnetic composite was characterized by TEM, FE-SEM, XRD,
- Mirhashemi, Fatemeh,Amrollahi, Mohammad Ali
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p. 2549 - 2563
(2019/02/13)
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- Synthesis and antimicrobial study of 1,4-dihydropyrano[2,3-c]pyrazole derivatives in the presence of amino-functionalized silica-coated cobalt oxide nanostructures as catalyst
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In this research a series of pyranopyrazoles were efficiently synthesized via the one-pot four-component reactions of ethyl acetoacetate, hydrazinehydrate, aldehydes and malononitrile in the presence of Co3O4@SiO2-tNH
- Shahbazi, Shakiba,Ghasemzadeh, Mohammad Ali,Shakib, Pegah,Zolfaghari, Mohammad Reza,Bahmani, Mahmoud
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p. 172 - 179
(2019/06/18)
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- Decoration of β-CD on Fe3O4@Ag core–shell nanoparticles as a new magnetically recoverable and reusable catalyst for the synthesis of 3,4-dihydropyrimidinones and 2,4-dihydropyrano[2,3-c]pyrazoles in H2O
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This report provides a description of the preparation and characterization of a Fe3O4@Ag-β-CD composite as a new magnetically recoverable catalyst for the synthesis of a number of biologically and pharmaceutically significant organic
- Mirhashemi, Fatemeh,Ali Amrollahi, Mohammad
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p. 568 - 575
(2018/11/25)
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- Application of Yttrium Iron Garnet as a Powerful and Recyclable Nanocatalyst for One-Pot Synthesis of Pyrano[2,3-c]pyrazole Derivatives under Solvent-Free Conditions
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The application of yttrium iron garnet (YIG) superparamagnetic nanoparticles as a new recyclable and highly efficient heterogeneous magnetic catalyst for one-pot synthesis of pyrano[2,3-c]pyrazole derivatives under solvent-free conditions, as well as etherification and esterification reactions are described. The advantages of the proposed method include the lack of organic solvents, clean reaction, rapid removal of the catalyst, short reaction times, excellent yields, and recyclability of the catalyst.
- Sedighinia,Badri,Kiasat
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p. 1755 - 1763
(2020/01/11)
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- Ag3[PMo12O40]: An efficient and green catalyst for the synthesis of highly functionalized pyran-annulated heterocycles via multicomponent reaction
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A facile, efficient and eco-friendly catalytic protocol was developed for the synthesis of medicinally important pyran-annulated heterocycles via multicomponent reaction (MCR). Cyclocondensation of differently substituted aromatic aldehydes, malononitrile
- Tamimi, Mehrnoush,Heravi, Majid M.,Mirzaei, Masoud,Zadsirjan, Vahideh,Lotfian, Nahid,Eshtiagh-Hosseini, Hossein
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- Alpha-Casein: an efficient, green, novel, and eco-friendly catalyst for one-pot multi-component synthesis of bis (pyrazol-5-ols), dihydro-pyrano[2,3-c]pyrazoles and spiropyranopyrazoles in an environmentally benign manner
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For the first time, alpha-Casein was used as an efficient and eco-friendly catalyst for an effective and facile preparation of dihydropyranopyrazoles and spiropyranopyrazoles. The synthesis of bis (pyrazol-5-ols) derivatives was developed via one-pot, pseudo-five-component condensation, and the target dihydropyrano[2,3-c]pyrazoles and spiropyranopyrazoles were prepared by one-pot four-component reaction. This new method of employing alpha-Casein, which is a green, recyclable, non-toxic and commercially available catalyst, offers advantages such as mild condition, short reaction times, easy work-up, no need for column chromatography, and high yields of the products which make it more economic than other environmentally synthetic protocols.
- Milani, Jalili,Maghsoodlou, Malek Taher,Hazeri, Nourallah,Nassiri, Mahmoud
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p. 1651 - 1664
(2019/04/25)
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- A convenient route toward one-pot multicomponent synthesis of spirochromenes and pyranopyrazoles accelerated via quinolinic acid
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In the present work, the catalytic activity of quinolinic acid (QUIN) was studied for the synthesis of spirochromene and pyranopyrazole derivatives from readily available materials. The salient features of these one-pot multicomponent protocols are the clean reaction profile, easy isolation of products, no chromatographic separation techniques, high efficiency, short reaction time, and high yield of products plus using QUIN as a new, inexpensive, commercially available, and efficient organocatalyst.
- Oudi, Maryam,Sanchooli Tazeh, Kazem,Hazeri, Nourallah,Fatahpour, Maryam,Ahmadi, Raheleh
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p. 1721 - 1728
(2019/06/08)
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- A concise route for the one-pot multi-component synthesis of 4,6-disubstituted 2-aminopyridine-3-carbonitriles and pyranopyrazoles using cobalt (II) nitrate hexahydrate as catalyst
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Three facile and efficient routes for one-pot, cobalt (II) nitrate hexahydrate catalyzed multi-component synthesis of 2-amino-3-cyanopyridine and pyranopyrazole derivatives have been developed. The present protocols offer the products in good yields from the simple and readily available starting materials. The other salient features of these protocols are operational simplicity, easy isolation of product without the need of column chromatographic purification, and the use of cobalt (II) nitrate hexahydrate as an efficient catalyst.
- Pejman, Hamed,Hazeri, Nourallah,Fatahpour, Maryam,Faroughi Niya, Homayoun
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p. 241 - 247
(2019/07/31)
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- Synergetic effects of naturally sourced metal oxides in organic synthesis: a greener approach for the synthesis of pyrano[2,3-c]pyrazoles and pyrazolyl-4H-chromenes
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Abstract: A clean and more economic protocol for the synthesis of pyrano[2,3-c]pyrazoles and pyrazolyl-4H-chromenes has been carried out using bael fruit ash (BFA) as a non-conventional natural catalyst in aqueous condition at ambient temperature. The catalyst was obtained from renewable resources by simple thermal treatment to dry rind of Aegle marmelos (Bael) fruit and formation of its active phase was confirmed by AAS, DSC-TGA, XRD, FT-IR, and SEM techniques. The BFA catalyst was found to be a green, highly active, easily biodegradable, and recyclable without loss of activity after the fifth run. The methodology provides an alternative platform to the conventional catalyzed process. Graphical Abstract: [Figure not available: see fulltext.].
- Shinde, Sachin K.,Patil, Megha U.,Damate, Shashikant A.,Patil, Suresh S.
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p. 1775 - 1795
(2017/12/06)
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- Highly functionalized pyranopyrazoles: synthesis, antimicrobial activity, simulation studies and their structure activity relationships (SARs)
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Abstract: Development of potent antibacterial and antifungal agents is a permanently new and unremitting investigation in the therapeutic field. Still, medicinal research wants to find the best antimicrobial agent. To attain this goal , here, the present work synthesis, simulation, and antimicrobial studies of pyranopyrazole derivatives were discussed. Among the reported compounds, 4b has dominant antimicrobial activity that was due to its higher dipole moment. Also, this compound has the most hydrophilic nature and low Eg value. Besides, compound 4e has the next higher dipole moment, hydrophilic property and efficient biological activity. The rationale of these results explained that the comparison of electronic results with biological data is the better way to find the potent pharmaceutical drug compounds. Graphical abstract: [Figure not available: see fulltext.]
- Reddy, Guda Mallikarjuna,Sravya, Gundala,Yuvaraja, Gutha,Camilo, Alexandre,Zyryanov, Grigory V.,Garcia, Jarem Raul
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p. 7491 - 7507
(2018/08/25)
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- A ternary hybrid system based on combination of mesoporous silica, heteropolyacid and double-layered clay: an efficient catalyst for the synthesis of 2,4-dihydro-3H-pyrazol-3-ones and pyranopyrazoles in aqueous medium: studying the effect of the synthetic
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SBA/hydrotalcite/heteropolyacid nanocomposite is synthesized via a novel procedure in which the as-prepared heteropolyacid-loaded SBA-15 was impregnated with calcined hydrotalcite. The ternary hybrid system was characterized by using SEM/EDS, XRD, BET, TP
- Sadjadi, Samahe,Heravi, Majid M.,Zadsirjan, Vahideh,Farzaneh, Vahid
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p. 6765 - 6785
(2018/07/13)
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- Synthesis of pyranopyrazoles using nano-Fe-[phenylsalicylaldiminemethylpyranopyrazole]Cl2 as a new Schiff base complex and catalyst
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By the condensation reaction of benzaldehyde with ethyl acetoacetate, malononitrile and hydrazine hydrate in the presence of FeCl2, a pyranopyrazole derivative was prepared which was then reacted with salicylaldehyde to afford nano-Fe-[phenylsalicylaldiminemethylpyranopyrazole]Cl2 (nano-[Fe-PSMP]Cl2). The prepared nano-Schiff base complex was fully characterized using Fourier transform infrared spectroscopy, X-ray diffraction, thermogravimetric analysis, differential thermogravimetry, scanning electron microscopy and UV–visible spectroscopy, and was used as an efficient and catalyst for the preparation of pyranopyrazoles.
- Moosavi-Zare, Ahmad Reza,Goudarziafshar, Hamid,Saki, Khadijeh
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- An efficient protocol for the one-pot four-component synthesis of 6-amino-1,4-dihydropyrano[2,3-c]-pyrazole-5-carbonitrile derivatives using starch solution as a reaction media
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An efficient, high-yielding and rapid protocol has been developed for the synthesis of 6-amino-l,4-dihydropyrano [2,3-c]pyrazol-5-carbonitrile derivatives through four-component, one-pot cyclocondensation reaction of ethyl acetoacetate, hydrazine hydrate, aldehydes and malononitrile utilizing starch solution as a highly efficient homogenous catalyst. The use of a nontoxic, reusable and biodegradable catalyst is one of the superior advantagesof this protocol. Short reaction times, mild conditions, excellent product yields, simple work-up procedure and non use of toxic organic solvents are added advantages of this procedure.
- Vekariya, Rajesh H.,Patel, Kinjal D.,Patel, Hitesh D.
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p. 576 - 582
(2019/05/21)
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- Sodium ascorbate as an expedient catalyst for green synthesis of polysubstituted 5-aminopyrazole-4-carbonitriles and 6-amino-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles
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Sodium ascorbate (SA) was used as a safe catalyst for the synthesis of 5-aminopyrazole-4-carbonitriles from the one-pot three-component cyclocondensation (3-CC) of aldehydes, phenylhydrazine, and malononitrile at 50?°C. This 3-CC proceeds in a mixture of
- Kiyani, Hamzeh,Bamdad, Maryam
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p. 2761 - 2778
(2018/01/27)
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- Ce(III) immobilized on aminated poly(vinyl chloride): high-performance synergistic bifunctional acid–base catalyst for one-pot synthesis of 1,4-dihydropyrano[2,3-c]pyrazoles
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A bifunctional acid–base catalyst of CeIII immobilized on ethylenediamine (EDA)-grafted poly(vinyl chloride) (PVC) has been prepared by a simple approach. First, PVC was treated with EDA to afford aminated poly(vinyl chloride) (PVC–EDA). Therea
- Zhang, Tianzhu,Zhou, Junbin,Chen, Yang,Li, Yiqun
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p. 5329 - 5344
(2018/08/21)
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- Ionic Liquid-catalyzed green protocol for Multi-component synthesis of dihydropyrano[2,3-c]pyrazoles as potential anticancer scaffolds
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A series of 6-amino-4-substituted-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles 5a–j were synthesized via one-pot, four-component condensation reactions of aryl aldehydes 1a–j, propanedinitrile (2), hydrazine hydrate (3) and ethyl acetoacetate (4) under solvent-free conditions. We report herein the use of the Br?nsted acid ionic liquid (BAIL) triethylammonium hydrogen sulphate [Et3NH][HSO4] as catalyst for this multi-component synthesis. Compared with the available reaction methodology, this new method has consistent advantages, including excellent yields, a short reaction time, mild reaction conditions and catalyst reusability. Selected synthesized derivatives were evaluated for in vitro anticancer activity against four human cancer cell lines viz. melanoma cancer cell line (SK-MEL-2), breast cancer cell line(MDA-MB-231), leukemia cancer cell line (K-562) and cervical cancer cell line (HeLa). Compounds 5b, 5d, 5g, 5h and 5j exhibited promising anticancer activity against all selected human cancer cell lines, except HeLa. Molecular docking studies also confirmed 5b and 5d as good lead molecules. An in silico ADMET study of the synthesized anticancer agents indicated good oral drug-like behavior and Non-toxic nature.
- Nimbalkar, Urja D.,Seijas, Julio A,Vazquez-Tato, Maria Pilar,Damale, Manoj G,Sangshetti, Jaiprakash N,Nikalje, Anna Pratima G
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- Synthesis, screening and docking of fused pyrano[3,2-d]pyrimidine derivatives as xanthine oxidase inhibitor
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In view of developing effective xanthine oxidase (XO) enzyme inhibitors, a series of 100 pyrano[3,2-d]pyrimidine derivatives was synthesized and evaluated for its in vitro XO enzyme inhibition. Structure activity relationship has also been established. Am
- Kaur, Manroopraj,Kaur, Amandeep,Mankotia, Suhani,Singh, Harbinder,Singh, Arshdeep,Singh, Jatinder Vir,Gupta, Manish Kumar,Sharma, Sahil,Nepali, Kunal,Bedi, Preet Mohinder Singh
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- Synthesis of Pyranopyrazoles under Eco-friendly Approach by Using Acid Catalysis
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Multicomponent synthesis of pyranopyrazole derivatives by using montmorillonite K-10 as a reusable green acid catalyst under eco-friendly method in the presence of eco-friendly solvent leads to novel protocol. Moreover, catalyst could be reused five times for the reaction without noticeable loss of activity. The scope of this path was to develop new synthetic molecules by using green catalysis for further screenings such as starting molecules for organic electronic materials and biological assays.
- Reddy, Guda Mallikarjuna,Raul Garcia, Jarem
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- Synthesis of pyrano[2,3-c]pyrazole derivatives using Fe3O4@SiO2@piperidinium benzene-1,3-disulfonate (Fe3O4@SiO2 nanoparticle-supported IL) as a novel, green and heterogeneous catalyst
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A simple, green and efficient protocol for the one-pot four-component synthesis of pyrano[2,3-c]pyrazole derivatives produced from reaction between aryl aldehydes, ethyl acetoacetate, malononitrile and hydrazine hydrate in the presence of nano magnetic piperidinium benzene-1,3-disulfonate was synthesized in water at 60 °C. The Fe3O4@SiO2 nanoparticle-supported IL was designed and synthesized. The present process offers advantages such as clean reaction, short reaction time, good to excellent yield, easy purification and easy recoverable catalyst.
- Ghorbani-Vaghei, Ramin,Mahmoodi, Jafar,Shahriari, Azadeh,Maghbooli, Yaser
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- Nano–Mn-[4-nitrophenyl-salicylaldimine-methyl pyranopyrazole]Cl2 as a new nanostructured Schiff base complex and catalyst for the synthesis of hexahydroquinolines
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By the reaction of 4-nitrobenzaldehyde with ethyl acetoacetate, malononitrile and hydrazine hydrate, pyranopyrazole derivative as an active biological compound was synthsized and then reacted with salicylaldehyde and MnCl2.4H2O to af
- Moosavi-Zare, Ahmad Reza,Goudarziafshar, Hamid,Ghaffari, Lida
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- Using magnetized water as a solvent for a green, catalyst-free, and efficient protocol for the synthesis of pyrano[2,3-c]pyrazoles and pyrano[4′,3′:5,6]pyrazolo [2,3-d]pyrimidines
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A facile, eco-friendly, and highly efficient one-pot four-component protocol is demonstrated for the synthesis of the pyrano[2,3-c]pyrazole and pyrano[4′,3′:5,6]pyrazolo [2,3-d]pyrimidine derivatives using magnetized water as a new green solvent. Simplici
- Bakherad, Mohammad,Keivanloo, Ali,Gholizadeh, Mostafa,Doosti, Rahele,Javanmardi, Mohaddese
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p. 1013 - 1029
(2017/02/10)
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- One-pot four-component synthesis of 1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles catalyzed by potassium phthalimide
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The potassium phthalimide (PPI) promoted a domino Knoevenagel-Michael-cyclocondensation of a wide variety of aldehydes, ethyl acetoacetate, malononitrile, and hydrazine derivatives to afford the 1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles in high yie
- Kiyani, Hamzeh,Bamdad, Maryam
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p. 221 - 226
(2017/07/22)
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- Electrochemically induced one pot synthesis of 1,4-dihydropyrano[2,3-c]-pyrazole-5-carbonitrile derivatives via a four component-tandem strategy
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An efficient one pot, multicomponent-tandem synthesis of highly functionalized 1,4-dihydropyrano[2,3-c]-pyrazole-5-carbonitrile is reported by electrochemically induced condensation of ethyl acetoacetate, hydrazine hydrate, malononitrile and various aroma
- Upadhyay, Abhishek,Sharma, Laxmi Kant,Singh, Vinay K.,Dubey, Rahul,Kumar, Narendra,Singh, Rana Krishna Pal
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supporting information
p. 1245 - 1249
(2017/03/10)
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- Synthesis of pyrano[2,3-c]pyrazoles by ionic liquids under green and eco-safe conditions
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Optimization of a green approach to the synthesis of pyrano[2,3-c]pyrazoles based on the one-pot, four-component condensation via a domino Knoevenagel/Michael/cyclization sequence was investigated. This method involved the evaluation of the activity of se
- Zakeri, Masoumeh,Nasef, Mohamed Mahmoud,Kargaran, Tina,Ahmad, Arshad,Abouzari-Lotf, Ebrahim,Asadi, Jahanbakhsh
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p. 717 - 728
(2017/02/10)
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- Piperidine-Promoted Three-Component Condensation: Synthesis of Chromene Heterocycles and Pyrazolotriazoles
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Chromenes, the oxygen-containing heterocyclic compounds, have a “special” place in biologically active natural products and in synthetic chemistry and in the fields of medicinal, agrochemical, cosmetic, and pigment industries. In this work, piperidine was used as a base catalyst for the convenient synthesis of 1,4-dihydropyrano[2,3-c]pyrazole, 5,10-dihydro-4H-benzo[g]chromene, and pyrazolo[1,2-a] [1,2,4]triazole derivatives at ambient temperature. This methodology has several advantages including the use of easily accessible and inexpensive catalysts, short reaction times, high yields, convenient work-up, and not needing column chromatography.
- Kangani, Mehrnoush,Hazeri, Nourallah,Yazdani-Elah-Abadi, Afshin,Maghsoodlou, Malek-Taher
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p. 1259 - 1269
(2017/10/18)
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- Aspirin: an efficient catalyst for synthesis of bis (pyrazol-5-ols), dihydropyrano[2,3-c]pyrazoles and spiropyranopyrazoles in an environmentally benign manner
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Abstract: This article aimed to present two facile and environmental friendly routes for the rapid assembly of?biologically active compounds including pyrazol core using aspirin as a novel and green catalyst. The synthesis of bis(pyrazol-5-ol) derivatives was developed via one-pot, pseudo-five-component condensation, and the target dihydropyrano[2,3-c]pyrazoles and spiropyranopyrazoles were prepared by one-pot, four-component reaction. These reactions can be performed in tandem from readily available starting materials. The main merits of the present methods are operational simplicity, no need for column chromatography, inexpensive materials, avoidance of harmless and corrosive acid catalysts, short reaction times, good yields of the products, and utilization of aspirin as a non-toxic, cheap, commercially available, and efficient catalyst.
- Fatahpour, Maryam,Noori Sadeh, Fatemeh,Hazeri, Nourallah,Maghsoodlou, Malek Taher,Lashkari, Mojtaba
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p. 1945 - 1956
(2017/08/14)
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