- Deep eutectic solvent mediated synthesis of 3,4-dihydropyrimidin-2(1H)-ones and evaluation of biological activities targeting neurodegenerative disorders
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Substitution of hazardous and often harmful organic solvents with “green” and “sustainable” alternative reaction media is always desirous. Ionic liquids (IL) have emerged as valuable and versatile liquids that can replace most organic solvents in a variet
- Asari, Asnuzilawati,Asif Nawaz, Muhammad,Hameed, Abdul,Iftikhar, Mehwish,Iqbal, Jamshed,Jalil, Saquib,Mohamad, Habsah,Rashid, Faisal,Saleem Khan, Maria,Ur Rehman, Atta,al-Rashida, Mariya
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- Composite of cross-linked chitosan beads and a cyclodextrin nanosponge: A metal-free catalyst for promoting ultrasonic-assisted chemical transformations in aqueous media
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A novel carbohydrate-based catalytic composite was prepared through covalent decoration of cross-linked chitosan beads with a cyclodextrin nanosponge. In this regard, chitosan beads were fabricated and cross-linked with glutaraldehyde. Subsequently, they
- Sadjadi, Samahe,Koohestani, Fatemeh
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- Sulfonic Acid and Ionic Liquid Functionalized Covalent Organic Framework for Efficient Catalysis of the Biginelli Reaction
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A quinoline-linked and ionic liquid-decorated covalent organic framework was prepared by incorporation of a multicomponent Povarov reaction and postsynthetic modification. The imidazolium and sulfonic acid-decorated COF-IM-SO3H can be a highly efficient B
- Yao, Bing-Jian,Wu, Wen-Xiu,Ding, Luo-Gang,Dong, Yu-Bin
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supporting information
p. 3024 - 3032
(2021/02/05)
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- ZnO Nanoparticles Embedded on a Reduced Graphene Oxide Nanosheet (ZnO?NPs@r-GO) as a Proficient Heterogeneous Catalyst for a One-Pot A3-Coupling Reaction
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This study reports a simple and facile route for the synthesis of ZnO nanoparticles (ZnO?NPs) decorated on reduced graphene oxide nanosheet (ZnO?NPs@r-GO) as a heterogeneous catalyst and tested over multicomponent one-pot A3-coupling reaction.
- Patel, Dikin,Modi, Chetan K.,Jha, Prafulla K.,Srivastava, Himanshu,Kane, Sanjeev R.
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supporting information
p. 3578 - 3590
(2021/09/09)
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- Deep eutectic solvent assisted synthesis of dihydropyrimidinones/thionesviaBiginelli reaction: theoretical investigations on their electronic and global reactivity descriptors
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Deep eutectic solvents formed from hydrated metal chlorides and hydrogen bond donors (Type 4) were prepared and their catalytic activity was compared for the synthesis of dihydropyrimidinones/thionesviaBiginelli reaction at room temperature. The one-pot m
- Shaibuna,Kuniyil, Muhammed Jeneesh Kariyottu,Sreekumar
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p. 20765 - 20775
(2021/11/23)
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- Copper-catalyzed one-pot relay synthesis of anthraquinone based pyrimidine derivative as a probe for antioxidant and antidiabetic activity
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Synthetic compounds have modernized the globe due to its vast applicable fields. Anthraquinones, as well as pyrimidine derivatives, are used as essential pharmacophores in the field of medicine. Maintenance of a green disease-free environment by using these derivatives is being acknowledged in developed as well as developing countries of the world. Considering the use of active catalysts in the synthesis of anthraquinone based derivatives are the era of concern for researchers due to their distinctive properties. Owing to the remarkable activities of anthraquinone and pyrimidine derivative, we synthesize compounds having both functionalities with the utilization of novel synergically active copper catalysts. This study explores the application of synthesized compounds using fast, ecofriendly and cost-effective approaches.1H and 13C NMR, antioxidant, antidiabetic, molecular docking and QSAR studies were used for characterization and evaluation of newly synthesized anthraquinone based pyrimidine derivatives. The result of these techniques shows that our desired compounds were successfully synthesized and have potent applications. Among all synthesized compounds, G2 and G3 showed a remarkable antioxidant activity with IC50 of 15.09 and 21.88 μg/ml respectively. While the compound G2 and G4 showed a strong inhibitory antidiabetic activity with the IC50 value of 24.23 and 28.94 μg/ml respectively. Furthermore, molecular docking results for both of the proteins assist the experimental data and confirms the different interactions between binding domains and substituent moieties. SAR study also relates to the experimental facts by giving us positive results of synthesized compounds. According to the QSAR study, G4 and G2 emerged as the most stable and most reactive compound among other compounds respectively. While MEP shows moderate to good nucleophilic and electrophilic reactivity of all four compounds.
- Ahmad, Zaheer,Arshad, Uzma,Parveen, Shagufta,Rafiq, Naila,Shafiq, Nusrat,Zarren, Gul
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- A comparative study between Cu(INA)2-MOF and [Cu(INA)2(H2O)4] complex for a click reaction and the Biginelli reaction under solvent-free conditions
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The catalytic activity of metal-organic framework Cu(INA)2 (INA = isonicotinate ion) and the complex [Cu(INA)2(H2O)4] were studied in the Copper-catalyzed Azide-Alkyne Cycloaddition (CuAAC) and Biginelli reactio
- Mansano Willig, Julia C.,Granetto, Gustavo,Reginato, Danielly,Dutra, Felipe R.,Poruczinski, érica Fernanda,De Oliveira, Isadora M.,Stefani, Helio A.,De Campos, Sílvia D.,De Campos, élvio A.,Manarin, Flávia,Botteselle, Giancarlo V.
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p. 3407 - 3415
(2020/02/04)
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- Concentrated solar radiation as a renewable heat source for a preparative-scale and solvent-free Biginelli reaction
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A well-known Biginelli reaction for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones was performed in an environmentally responsible manner. Large numbers of substrates were screened, and found to give excellent yields of the desired products. In
- Gadkari, Yatin U.,Hatvate, Navnath T.,Takale, Balaram S.,Telvekar, Vikas N.
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supporting information
p. 8167 - 8170
(2020/06/09)
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- Bentonite with high loading of ionic liquid: A potent non-metallic catalyst for the synthesis of dihydropyrimidinones
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In attempt to devise an environmentally-benign metal-free catalyst, ionic liquid was supported on bentonite that is a natural clay. To enhance the loading of ionic liquid, bentonite was first functionalized with a dendritic moiety through successive react
- Koohestani, Fatemeh,Sadjadi, Samahe
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- Natural dolomitic limestone-catalyzed synthesis of benzimidazoles, dihydropyrimidinones, and highly substituted pyridines under ultrasound irradiation
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Natural dolomitic limestone (NDL) is employed as a heterogeneous green catalyst for the synthesis of medicinally valuable benzimidazoles, dihydropyrimidinones, and highly functionalized pyridines via C–N, C–C, and C–S bond formations in a mixture of ethan
- Godugu, Kumar,Gundala, Trivikram Reddy,Mohinuddin Pinjari, Mohammad Khaja,Reddy Nallagondu, Chinna Gangi,Sanapareddy, Lakshmi Reddy,Sri Yadala, Venkata Divya
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supporting information
p. 1881 - 1900
(2020/10/02)
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- Dihydropyrimidinones: Efficient one-pot green synthesis using Montmorillonite-KSF and evaluation of their cytotoxic activity
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A simple, efficient, cost-effective, recyclable and green approach has been developed for the synthesis of new dihydropyrimidinone analogs via the Biginelli reaction. The methodology involves a multicomponent reaction catalyzed by "HPA-Montmorillonite-KSF"as a reusable and heterogeneous catalyst. This method gives an efficient and much improved modification of the original Biginelli reaction, in terms of yield and short reaction times under solvent free conditions. All the derivatives were subjected to cytotoxicity screening against a panel of four different human cancer cell lines viz. colon (Colo-205), prostate (PC-3), leukemia (THP-1) and lung (A549) to check their effect on percentage growth. MTT [3-(4,5-dimethylthiazol-yl)-diphenyl tetrazoliumbromide] cytotoxicity assay was employed to check IC50 values. Of the synthesized analogs, 16a showed the best activity with IC50 of 7.1 ± 0.8, 13.1 ± 1.4, 13.8 ± 0.9 and 14.7 ± 1.1 μM against lung (A549), leukemia (THP-1), prostate (PC-3) and colon (Colo-205) cancer lines, respectively. The 16a analog was further checked for its effect on cancer cell properties through clonogenic (colony formation) and scratch motility (wound healing) assays and thereby was found that it reduced both the colony formation and migratory properties of the lung cancer cell line (A549). Further, molecular docking studies were performed with 16a to show its binding mode. This journal is
- Alharthi, Fahad A.,Alsalme, Ali,Dar, Bashir A.,Farooq, Saleem,Hamid, Abid,Hussain, Aashiq,Koul, S.
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p. 42221 - 42234
(2020/12/09)
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- Efficient one-pot synthetic methods for the preparation of 3,4-dihydropyrimidinones and 1,4-dihydropyridine derivatives using BNPs?SiO2(CH2)3NHSO3H as a ligand and metal free acidic heterogeneous nano-catalyst
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Heterocyclic compounds with biological and pharmacological activates like 3,4-dihydropyrimidin-2-(1H)-ones and 1,4-dihydropyridines have attracted great interest. Boehmite nanoparticles functionalized with silylpropyl sulfamic acid (BNPs?SiO2(C
- Bahrami, Kiumars,Khodamorady, Minoo,Sohrabnezhad, Samira
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- Phosphotungstic acid - Jeffamine? hybrid catalyst for one-pot Biginelli reaction starting from benzyl alcohol
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Herein, we report the catalytic action of phosphotungstic acid - Jeffamine? hybrid (PTA-Jeffamine?) for the synthesis of dihydropyrimidinones (DHPMs) starting from benzyl alcohol by Biginelli reaction in water in a one-pot system. Hydrogen peroxide was used as oxidizing agent instead of the conventional nitrate salts. A two-step and a one-step protocol was used to evaluate the catalytic activity. Both processes showed appreciable results with the one-pot one-step protocol demonstrating appreciable yield (87 percent) of DHPM within 5.5 h at pH 7.5. No acid was added and the pH was adjusted by controlling ratio of PTA/ Jeffamine?. Catalytic results were compared with literature reports for one-pot one-step Biginelli reactions starting from benzyl alcohol. Biginelli products were characterized by UV-visle–vis, FT-IR, NMR spectroscopy. DHPMs formed from the two-step process demonstrated appreciable anticancer activity. The present work may lead to the development of industry-friendly, non-toxic and scalable catalyst for one-pot Biginelli reactions.
- Bhattacharjee, Rama Ranjan,Jeyaraj, Sankarganesh,Mahendran, Hema Priya,Mohanta, Kallol,Suppan, Thangamani
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- Photo-oxidation coupled Kabachnik-Fields and Bigenelli reactions for direct conversion of benzyl alcohols to α-aminophosphonates and dihydropyrimidones
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A tandem one-pot solvent free approach for the direct conversion of benzyl alcohols to α-amino phosphonates and dihydropyrimidones is reported. The method relies on a metal free photo-oxidation of benzyl alcohols to benzaldehydes under UV irradiation using ammonium perchlorate followed by Kabachnik-Fields and Biginelli reactions. The reaction conditions are moderate and metal free with good substrate scope. The control experiments were performed to investigate the role of the ammonium perchlorate and molecular oxygen as oxidants. The quenching experiments in the presence of TEMPO and other radical quenchers suggest radical based mechanism.
- Ali, Gazunfor,Ara, Tabassum,Dangroo, Nisar A.,Naqvi, Tahira,Raheem, Shabnam,Rizvi, Masood Ahmad
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p. 195 - 202
(2020/04/01)
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- A Bifunctional Metal/Acid Catalyst for One-pot Multistep Synthesis of Pharmaceuticals
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Abstract: One inhibitor of the fatty acid transporter FATP4 was synthesized in a three steps one-pot process in the presence of a bifunctional metal/acid catalyst. This molecule which has potential interest for the treatment of the obesity in orlistat (Xenical TM) analogue-based therapies has a 3,4-dihydropyrimidin-2(1H)-one (DHPM) scaffold and was obtained by means of a three one-pot process through successive oxidation, cyclocondensation and transesterification reactions. The one-pot strategy was extended to the synthesis of a series of related ester DHPM derivatives.
- Corma, Avelino,Lopez-Prado, Maria Victoria,Sabater, María J.
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p. 499 - 507
(2020/05/25)
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- Evaluation of alcohols as substrates for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones under environmentally friendly conditions
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The aim of this research was to develop a procedure for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones under environmentally friendly conditions using alcohols as the starting materials in aqueous media. The developed protocol resulted in 3,4-dihydropyrimidin-2(1H)-ones derivatives, which are relevant intermediates with therapeutic and pharmacological properties. Target products were synthetized in a tandem process, which meets the requirements of pharmaceutical chemistry. The influence of the reaction conditions was investigated, and as a result, various substituted 3,4-dihydropyrimidin-2(1H)-ones were obtained with a yield of up to 81percent, free from heavy metal impurities.
- K?ciek, Aleksandra,Koszelewski, Dominik,Ostaszewski, Ryszard,Paprocki, Daniel
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- Highly Efficient Synthesis of Substituted 3,4-Dihydropyrimidin-2-(1H)-ones (DHPMs) Catalyzed by Hf(OTf)4: Mechanistic insights into reaction pathways under metal Lewis acid catalysis and solvent-free conditions
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In our studies on the catalytic activity of Group IVB transition metal Lewis acids, Hf(OTf)4 was identified as a highly potent catalyst for”one-pot, three-component” Biginelli reaction. More importantly, it was found that solvent-free conditions, in contrast to solvent-based conditions, could dramatically promote the Hf(OTf)4-catalyzed formation of 3,4-dihydro-pyrimidin-2-(1H)-ones. To provide a mechanistic explanation, we closely examined the catalytic effects of Hf(OTf)4 on all three potential reaction pathways in both “sequential bimolecular condensations” and “one-pot, three-component” manners. The experimental results showed that the synergistic effects of solvent-free conditions and Hf(OTf)4 catalysis not only drastically accelerate Biginelli reaction by enhancing the imine route and activating the enamine route but also avoid the formation of Knoevenagel adduct, which may lead to an undesired byproduct. In addition, 1H-MMR tracing of the H-D exchange reaction of methyl acetoacetate in MeOH-d4 indicated that Hf(IV) cation may significantly accelerate ketone-enol tautomerization and activate the β-ketone moiety, thereby contributing to the overall reaction rate.
- Kong, Rui,Han, Shuai-Bo,Wei, Jing-Ying,Peng, Xiao-Chong,Xie, Zhen-Biao,Gong, Shan-Shan,Sun, Qi
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- Biginelli reaction via bis-ureide intermediate in low melting mixture
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This paper deals with the study of mechanism of the Biginelli reaction using low melting mixture as solvent and catalyst. The catalytic effect of low melting mixture and the reaction mechanism is discussed on the basis of nuclear magnetic resonance (NMR)
- Mahajan, Hitesh,Jamwal, Babita,Paul, Satya
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p. 585 - 593
(2019/09/30)
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- Tuning the Biginelli reaction mechanism by the ionic liquid effect: The combined role of supported heteropolyacid derivatives and acidic strength
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Herein, a combination of heteropolyacids and ionic liquids as a catalytic system was studied for the Biginelli multicomponent reaction; the positive ionic liquid effect associated with the acidic strength of zeolite-supported heteropolyacids made this com
- Freitas, Elon F.,Souza, Roberto Y.,Passos, Saulo T. A.,Dias, José A.,Dias, Silvia C. L.,Neto, Brenno A. D.
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p. 27125 - 27135
(2019/09/13)
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- CoFe2O4/TMU-17-NH2 as a hybrid magnetic nanocomposite catalyst for multicomponent synthesis of dihydropyrimidines
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A new magnetic metal–organic framework nanocomposite (CoFe2O4/TMU-17-NH2) was prepared via an embedding approach by synthesis of the metal–organic framework crystals in the presence of magnetic cobalt ferrite nanoparticles. We demonstrated that the resulting magnetic nanocomposite can serve as a recyclable nanocatalyst for one-pot synthesis of bis-3,4-dihydropyrimidin-2(1H)-one and 3,4-dihydropyrimidin-2(1H)-one derivatives via three-component reaction of 1,3-diketone, urea or thiourea and aromatic aldehyde under solvent-free conditions. CoFe2O4/TMU-17-NH2 was characterized using various techniques. The recovery of the nanocomposite was achieved by a simple magnetic decantation and it was reused at least seven times without significant degradation in catalytic activity.
- Yadollahi, Mahtab,Hamadi, Hosein,Nobakht, Valiollah
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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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- Ultrasound aided solvent-free synergy: an improved synthetic approach to access 3,4-dihydropyrimidin-2(1H)-ones
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Abstract: A remarkably simple synthetic method has been described for the access of structurally diverse 3,4-dihydropyrimidin-2(1H)-ones in excellent yields in the presence of 2,4,6-trichloro-1,3,5-triazine (TCT) as an efficient source of hydrochloric aci
- Ramesh, Rathinam,Ramesh, Samikannu,Malecki, Jan Grzegorz,Lalitha, Appaswami
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p. 1197 - 1205
(2019/04/30)
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- Synthesis of a 2-Hydrazinyl-1,6-dihydropyrimidine Derivative
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Ethyl 4-methyl-6-phenyl-2-[2-(propan-2-ylidene)hydrazinyl]-1,6-dihydropyrimidine-5-carboxylate has been synthesized from ethyl 2-(ethoxymethylidene)-7-methyl-3-oxo-5-phenyl-3,5-dihydro-2H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate.
- Shiryaev,Lashmanova,Trofimova
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p. 335 - 338
(2019/05/16)
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- Efficient Catalytic Synthesis of 3,4-Dihydropyrimidin-2-ones/thiones via Little Acidic Ionic Liquid Combined with Rapid Heating Ways
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Catalytic synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones was efficiently promoted by as little as 2.5?mol% of Br?nsted acidic ionic liquid [(CH2)3SO3HMIM]HSO4 catalyst loading via rapid heating ways. Inter
- Zhang, Guo-Ping,Tian, Da-Yu,Shi, Wang-Ming
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p. 2522 - 2531
(2018/09/29)
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- T3P-DMSO mediated one-pot tandem approach for the synthesis of 3,4-Dihydropyrimidin-2(1H)-ones/thiones from alcohols
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Background: Biginelli reaction is one of the most important multiple-component chemical reactions which creates 3,4-dihydropyrimidin-2(1H)-ones. Even though Biginelli reaction was reported over a century using different substrates, literature lacks the ex
- Vinaya, Kambappa,Shivaramu, Prasanna D.,Chandrashekara, Ganganahalli K.,Chandrappa, Siddappa,Rangappa, Kanchugarakoppal S.
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p. 241 - 245
(2018/04/20)
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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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- Room temperature synthesis of 3,4-dihydropyrimidin-2(1H)-one using apatite like oxyphosphate
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An oxyphosphate of formula BiCa4(PO4)3O was prepared and characterized by powder XRD, Fourier transform infrared spectroscopy (FTIR), and SEM-EDAX techniques. The catalytic activity of the synthesized compound was explored
- Sumathi,Buvaneswari
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p. 961 - 965
(2017/08/10)
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- A highly efficient and green catalytic synthesis of 3,4-dihydro-pyrimidin-2-(1H)-ones (thiones) using 3-sulfonic acid-1-imidazolopyridinium hydrogen sulfate under solvent-free conditions
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The ionic liquid catalyst 3-sulfonic acid-1-imidazolopyridinium hydrogen sulfate, [Simp]HSO4 was found to be a highly active and green catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones (thiones) under the solvent-free conditions. Av
- Bakherad, Mohammad,Javanmardi, Mohaddeseh,Doosti, Raheleh,Tayebee, Reza
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- A New Type of Magnetically-Recoverable Heteropolyacid Nanocatalyst Supported on Zirconia-Encapsulated Fe3O4 Nanoparticles as a Stable and Strong Solid Acid for Multicomponent Reactions
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Abstract: A novel highly efficient magnetically retrievable catalyst was developed by the immobilization of H3PW12O40 (20–60 wt%) on the surface of zirconia-encapsulated Fe3O4 nanoparticles. The prepared HPW supported on nano-Fe3O4@ZrO2 heterogeneous acid catalyst (or n-Fe3O4@ZrO2/HPW) was fully characterized by several physicochemical techniques such as: Fourier transform infrared spectroscopy (FT-IR), field emission scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, X-ray diffraction, vibrating sample magnetometry and thermogravimetric analysis. The FT-IR spectroscopic data revealed that H3PW12O40 molecules on the nano-Fe3O4@ZrO2 support existed in the Keggin structure. The acidity of the catalyst was measured by the help of a potentiometric titration with n-butylamine. It was surprising that this very strong solid acid catalyst exhibited an excellent acid strength which was as a result of possessing a higher number of surface active sites compared to its homogeneous analogues. The catalytic activity of the as-prepared novel nano-Fe3O4@ZrO2/HPW was explored through the one-pot three-component synthesis of different 3,4-dihydropyrimidin-2(1H)-ones (i.e. Biginelli reaction) and 1,4-dihydropyridines (i.e. Hantzsh reaction) under solvent free condition. The sample of 40 wt% showed higher acidity and activity in the catalytic transformation. After the reaction, the catalyst/product isolation could be easily achieved with an external magnetic field and the catalyst could be easily recycled for at least five times without any decrease in its high catalytic activity. The excellent recyclability was attributed to the strong interaction between the hydroxyl groups of the nano-Fe3O4@ZrO2 support and the HPW species. Graphical Abstract: [Figure not available: see fulltext.].
- Zolfagharinia, Somayeh,Kolvari, Eskandar,Koukabi, Nadiya
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p. 1551 - 1566
(2017/05/17)
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- Biginelli reaction of vicinal diols: A new route for one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives
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Background: 3,4-Dihydropyrimidin-2(1H)-one derivatives are an important class of nitrogen heterocycles. These compounds present a wide range of biological activities viz antibacterial, antifungal, and antidiabetic. Although many synthetic methods are available in the literature for the synthesis of these molecules, many of these methods have their own limitations such as use of excess of expensive catalyst and poor yields. Methods: The synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives is developed through the reaction of 1,2-diols, ethyl acetoacetate and urea in the presence of lead tetraacetate in dry ethanol under reflux conditions. Results: A series of 3,4-dihydropyrimidin-2(1H)-one derivatives were synthesized in good yields (82-95%) under reflux for 2-3.5 hours in ethanol solvent. The structural assignments of these compounds were made on the basis of elemental analysis and spectroscopic data. Conclusion: This protocol is an alternative to existing procedure for the synthesis of Biginelli compounds. The present methodology reduces the number of steps in total synthesis.
- Jagadishbabu, Narasashetty,Shivashankar, Kalegowda
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p. 330 - 336
(2017/07/26)
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- A green approach for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones (and -thiones) using N,N-diethyl-N-sulfoethanaminium hydrogen sulfate
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In this paper, a novel SO3H-containing ionic liquid namely N,N-diethyl-N-sulfoethanaminium hydrogen sulfate ([Et3N-SO3H]HSO4) has been synthesized, and characterized by studying its FT-IR, 1H NMR, su
- Zare, Abdolkarim,Nasouri, Zahra
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p. 364 - 369
(2016/02/03)
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- Nano-ZrO2 sulfuric acid: A heterogeneous solid acid nano catalyst for Biginelli reaction under solvent free conditions
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Nano-ZrO2 sulfuric acid [n-ZrO2-SO3H (n-ZrSA)] has been synthesized from the reaction of nano-ZrO2 with chlorosulfonic acid as sulfonating agent. This catalyst was characterized via FT-IR, XRD, TGA, FESEM, TEM,
- Kolvari, Eskandar,Koukabi, Nadiya,Hosseini, Maliheh M.,Vahidian, Mitra,Ghobadi, Elham
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p. 7419 - 7425
(2016/07/13)
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- A unique opportunity for the utilization of glass wastes as a resource for catalytic applications: toward a cleaner environment
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Although glass recycling has been conducted since 1970s, and even though recycled glass waste has been used in the construction of various alternative products, the utilization of glass waste for catalytic applications has not been fully considered until
- Zolfagharinia, Somayeh,Koukabi, Nadiya,Kolvari, Eskandar
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p. 113844 - 113858
(2016/12/24)
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- USE OF COMPOSITIONS OBTAINED BY CALCINING PARTICULAR METAL-ACCUMULATING PLANTS FOR IMPLEMENTING CATALYTICAL REACTIONS
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The use of metal-accumulating plants for implementing chemical reactions especially catalytical reactions.
- -
-
Paragraph 0597; 0621
(2016/01/25)
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- Urease: A highly biocompatible catalyst for switchable Biginelli reaction and synthesis of 1,4-dihydropyridines from the in situ formed ammonia
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Urease is a superior biocompatible catalyst for switching from the Biginelli reaction to urea-based synthesis of 1,4-dihydropyridines in water, where 100% switching occurs at 0.02 g/mL of enzyme. Hantzsch reaction with ammonium acetate (NH4OAc) is inefficiently catalyzed by urease (70%, 4 h), and heavy metal ions inhibit the urease-catalyzed reactions with urea or NH4OAc. Promotion of the urea-based Hantzsch reaction by urease and its inhibition with Hg2 + supports specificity of urease for in situ generation of ammonia, whereas the role of urease in further transformations is not so specific. The features of this enzymatic method are reusability, mild reaction conditions, biocompatibility, generality, and high yield of products.
- Tamaddon, Fatemeh,Ghazi, Somayeh
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- The Biginelli reaction under batch and continuous flow conditions: Catalysis, mechanism and antitumoral activity
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Two novel coordination polymers (CPs) have been synthesized, characterized and successfully applied as robust heterogeneous catalysts for the Biginelli multicomponent reaction to obtain 3,4-dihydropyrimidin-2(1H)-one or thione (DHPMs) derivatives. The rea
- Silva, Gabriel C. O.,Correa, Jose R.,Rodrigues, Marcelo O.,Alvim, Haline G. O.,Guido, Bruna C.,Gatto, Claudia C.,Wanderley, Kaline A.,Fioramonte, Mariana,Gozzo, Fabio C.,De Souza, Rodrigo O. M. A.,Neto, Brenno A. D.
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p. 48506 - 48515
(2015/06/16)
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- Ga(OTf)3 catalyzed synthesis of 1,4-dihydropyrimidin-2(1H)-ones
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Gallium(III) triflate was used to catalyze Biginelli-like reactions under solvent-free condition to obtain dihydropyrimidinone derivatives in good to excellent yields and short reaction time.
- Xia, Jingjing,Zhang, Kehua
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p. 105 - 112
(2015/03/04)
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- Cobalt manganese oxide nano catalysts as a recyclable catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones-thiones
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A simple and effective synthesis of 3,4-dihydropyrimidin-2(1H)-one and thione derivatives has been developed in the presence of nano cobalt manganese oxide as catalyst under thermal solvent-free conditions. The proposed procedure ensures easy to handle, r
- Karami, Changiz,Mohammadi, Hadi,Ghodrati, Keivan,Ahmadian, Hossein,Jamshidi, Fariba,Nouri, Maryam,Haghnazarie, Nahid
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p. 271 - 276
(2015/08/11)
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- Synthesis of dihydropyrimidine α,μ3-diketobutanoic acid derivatives targeting HIV integrase
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The synthesis and antiviral evaluation of a series of dihydropyrimidinone and thiopyrimidine derivatives bearing aryl α,γ-diketobutanoic acid moiety are described using the Biginelli multicomponent reaction as key step. The most active among 20 synthesized novel compounds were 4c, 4d and 5b, which possess nanomolar HIV-1 integrase (IN) stand transfer (ST) inhibition activities. In order to understand their mode of interactions within the IN active site, we docked all the compounds into the previously reported X-ray crystal structure of IN. We observed that compounds 4c, 4d and 5b occupied an area close to the two catalytic Mg2+ ions surrounded by their chelating triad (E221, D128 and D185), DC16, Y212 and the β-diketo acid moiety of 4c, 4d and 5b chelating Mg2+. As those compounds lack anti-HIV activities in cell, their prodrugs were synthetized. The prodrug 4c′ exhibited an anti-HIV activity of 0.19 μM in primary human lymphocytes with some cytotoxicity. All together, these results indicate that the new analogs potentially interact within the catalytic site with highly conserved residues important for IN catalytic activity.
- Sari, Ozkan,Roy, Vincent,Métifiot, Mathieu,Marchand, Christophe,Pommier, Yves,Bourg, Stéphane,Bonnet, Pascal,Schinazi, Raymond F.,Agrofoglio, Luigi A.
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p. 127 - 138
(2015/10/28)
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- Natural organic acids promoted synthesis of 3, 4-dihydropyrimidin-2(1H)-ones/thiones under solvent-free conditions
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Naturally occurring organic acids are reported to be highly efficient promoters for the Biginelli reaction under thermal and microwave irradiation using solvent free conditions. Among the various organic acids used, malic acid was found to be the most eff
- Thorat, Nitin M.,Thopate, Shankar R.
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p. 210 - 216
(2015/06/23)
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- Functionalized S-perfluorinated sulfoximines: Preparation and evaluation in catalytic processes
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N-substituted S-perfluoroalkylated sulfoximines were synthesized from the NH sulfoximines either by a copper coupling reaction with aryl halides or by a reaction with electrophilic substrates. The procedure allowed the preparation of N,N′-bridged bis sulf
- Le, Thanh-Nghi,Diter, Patrick,Pégot, Bruce,Bournaud, Chloée,Toffano, Martial,Guillot, Regis,Vo-Thanh, Giang,Yagupolskii, Yurii,Magnier, Emmanuel
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p. 179 - 187
(2015/11/10)
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- Solvent-Free Ball-Milling Biginelli Reaction by Subcomponent Synthesis
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We report here an understanding of systems chemistry on small molecules through covalent mechanochemistry. As a proof-of-concept, the multicomponent Biginelli reaction by subcomponent synthesis was considered as a model system. Reactions were performed un
- Sahoo, Prasit Kumar,Bose, Anima,Mal, Prasenjit
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supporting information
p. 6994 - 6998
(2015/11/16)
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- Highly efficient and magnetically recoverable niobium nanocatalyst for the multicomponent biginelli reaction
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A new magnetically recoverable nanocatalyst was prepared by coating magnetite with niobium oxide (Fe3O4@Nb2O5) by using a simple wet impregnation method. The Fe3O4@Nb2O5/su
- Lima, Carolina G. S.,Silva, Sandrina,Gonalves, Ricardo H.,Leite, Edson R.,Schwab, Ricardo S.,Corra, Arlene G.,Paixo, Mrcio W.
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p. 3455 - 3463
(2015/04/16)
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- A simple and efficient synthesis of 3,4-dihydropyrimidin-2-(1H)-ones via Biginelli reaction catalyzed by nanomagnetic-supported sulfonic acid
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Nanomagnetic-supported sulfonic acid is found to be a new, powerful, and reusable heterogeneous catalyst for the rapid synthesis of 3,4-dihydropyrimidin- 2-(1H)-ones under conventional heating and microwave irradiation. This is the first example of combin
- Kolvari, Eskandar,Koukabi, Nadiya,Armandpour, Ozra
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supporting information
p. 1383 - 1386
(2014/02/14)
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- Manganese-containing periodic mesoporous organosilica with ionic-liquid framework (Mn@PMO-IL): A powerful, durable, and reusable nanocatalyst for the biginelli reaction
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The catalytic application of a novel manganese-containing periodic mesoporous organosilica with ionic-liquid framework (Mn@PMO-IL) in the Biginelli reaction was investigated. First, the Mn@PMO-IL nanocatalyst was prepared and characterized by TEM, SEM, X-
- Elhamifar, Dawood,Shabani, Ahmad
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supporting information
p. 3212 - 3217
(2014/03/21)
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- Carbon nanotubes supported by titanium dioxide nanoparticles as recyclable and green catalyst for mild synthesis of dihydropyrimidinones/thiones
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The catalytic activity of titanium dioxide supported on carbon nanotubes has been investigated in a one-pot three components condensation reaction (Biginelli reaction). The TiO2-CNT nanocomposites as catalyst are highly stable and completely he
- Safari, Javad,Gandomi-Ravandi, Soheila
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p. 241 - 247
(2014/05/06)
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- Graphite catalyzed solvent free synthesis of dihydropyrimidin-2(1H)-ones/ thiones and their antidiabetic activity
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A solvent free three component condensation reaction between an aldehyde, ethyl acetoacetate and urea catalyzed by graphite, a green catalyst is described for the synthesis of dihydropyrimidin-2(1H)-ones. This protocol is scalable and the catalyst is reus
- Dhumaskar, Kashinath L.,Meena, Surya Nandan,Ghadi, Sanjeev C.,Tilve, Santosh G.
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p. 2897 - 2899
(2014/06/10)
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- Li(glycine)(CF3SO3) as an effective and recoverable catalyst for the preparation of 3,4-dihydropyrimidine-2-(1H)-one under solvent-free conditions
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An efficient solvent-free protocol for the synthesis of 3,4-dihydropyrimidine-2-(1H)-one by the one-pot condensation of aldehyde, ethyl acetoacetate and urea using Li(glycine)(CF3SO3) as a reusable acidic ionic liquid is reported. These reactions have the advantages in this work of clean reaction, simple purification, short reaction time and high yields.
- Abbaspour-Gilandeh, Esmayeel,Azimi, Seyyedeh Cobra,Mohammadi-Barkchai, Aidin
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p. 54854 - 54863
(2015/02/05)
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- Basic isoreticular nanoporous metal-organic framework for Biginelli and Hantzsch coupling: IRMOF-3 as a green and recoverable heterogeneous catalyst in solvent-free conditions
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The IRMOF-3 metal-organic framework (MOF) acts as a suitable green catalyst for the one-pot synthesis of dihydropyrimidinone and dihydropyridine derivatives through the Biginelli and Hantzsch reactions, and the desired products were obtained in high yield
- Rostamnia, Sadegh,Morsali, Ali
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p. 10514 - 10518
(2014/03/21)
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- The biginelli reaction with an imidazolium-tagged recyclable iron catalyst: Kinetics, mechanism, and antitumoral activity
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The present work describes the synthesis, characterization, and application of a new ion-tagged iron catalyst. The catalyst was employed in the Biginelli reaction with impressive performance. High yields have been achieved when the reaction was carried ou
- Ramos, Luciana M.,Guido, Bruna C.,Nobrega, Catharine C.,Corrêa, José R.,Silva, Rafael G.,De Oliveira, Heibbe C. B.,Gomes, Alexandre F.,Gozzo, Fábio C.,Neto, Brenno A. D.
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supporting information
p. 4156 - 4168
(2013/05/08)
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