cas 33458-26-3, ETHYL 6-METHYL-4-PHENYL-2-THIOXO-1,2,3,4-TETRAHYDROPYRIMIDINE-5-CARBOXYLATE

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Synthesis method of dihydropyrimidinone compound
The invention discloses a synthesis method of a dihydropyrimidone compound, which belongs to the technical field of organic synthesis, and comprises the following steps: by taking benzaldehyde or a derivative thereof, ethyl acetoacetate or acetylacetone a
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Paragraph 0034-0036; 0040-0041; 0044; 0070-0075; 0077

(2021/05/19)

Deep eutectic solvent assisted synthesis of dihydropyrimidinones/thionesviaBiginelli reaction: theoretical investigations on their electronic and global reactivity descriptors
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
p. 20765 - 20775
(2021/11/23)

Sulfonic Acid and Ionic Liquid Functionalized Covalent Organic Framework for Efficient Catalysis of the Biginelli Reaction
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
p. 3024 - 3032
(2021/02/05)

A highly efficient one-pot multicomponent synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones catalyzed by strontium pyroarsenate nano-plates
The present work describes the one-pot multicomponent synthesis of heterocyclic 3,4-dihydropyrimidin-2-(1H)-ones and thiones (DHPMs) under solvent-free conditions by Sr2As2O7 nanocatalyst. Sr2As2Osub
Esmaeili, Rozhin,Kafi-Ahmadi, Leila,Khademinia, Shahin
(2020/05/01)

Natural dolomitic limestone-catalyzed synthesis of benzimidazoles, dihydropyrimidinones, and highly substituted pyridines under ultrasound irradiation
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
supporting information
p. 1881 - 1900
(2020/10/02)

Dihydropyrimidinones: Efficient one-pot green synthesis using Montmorillonite-KSF and evaluation of their cytotoxic activity
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.
p. 42221 - 42234
(2020/12/09)

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
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
(2020/01/23)

Polymeric imidazolium ionic liquid-tagged manganese Schiff base complex: an efficient catalyst for the Biginelli reaction
Abstract: In this study, a new organometallic catalyst including polymeric imidazolium ionic liquid-functionalized Mn(III) Schiff base complex (PIL-SB-Mn(III)) was prepared and characterized using various analyses like FTIR, H-NMR, FE-SEM, EDX, TGA, and ICP-OES. Then, the applications of catalyst were tested in the synthesis of 3,4-dihydropyrimidine-2(1H)-one/thiones under solvent-free conditions. This polymeric ionic liquid catalyst can carry out the Biginelli reaction in less than an hour in good to excellent yields. The recovered catalyst has been characterized by FTIR and EDX analyses; heterogeneous nature of this catalyst has been confirmed successfully. Graphic abstract: [Figure not available: see fulltext.].
Mashhoori, Mahboobeh-Sadat,Sandaroos, Reza,Zeraatkar Moghaddam, Ali
p. 4939 - 4954
(2020/09/01)

Air-stable zirconium (IV)-salophen perfluorooctanesulfonate as a highly efficient and reusable catalyst for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones under solvent-free conditions
An air-stable complex of zirconium (IV)-salophen perfluorooctanesulfonate (1) was successfully synthesized by reacting Zr (salphen)Cl2 and C8F17SO3Ag. Complex 1 was characterized and studied by different techniq
Li, Ningbo,Wang, Yijun,Liu, Feijun,Zhao, Xin,Xu, Xinhua,An, Quan,Yun, Keming
(2020/01/22)

Tuning the Biginelli reaction mechanism by the ionic liquid effect: The combined role of supported heteropolyacid derivatives and acidic strength
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.
p. 27125 - 27135
(2019/09/13)

Method for catalytically synthesizing 3, 4-dihydropyrimidine-2 (1H)-ketone in green manner
The invention discloses green catalytic Biginelli reaction, and discloses a method for synthesizing 3, 4-dihydropyrimidine-2 (1H)-ketone and derivatives thereof by the aid of 'one-pot processes'. Resin D732 is used as a catalyst, ethyl alcohol is used as a solvent, and the usage of the catalyst is 0.2g/1mmoL aldehyde. The method includes carrying out reflux reaction at the temperatures of 78 DEG Cfor 1-5 hours; filtering out the resin after the reaction is completely carried out; cooling filter liquor by the aid of ice water and then carrying out filter, ethyl alcohol re-crystallization and drying to obtain pure products. Compared with the traditional methods for synthesizing 3, 4-dihydropyrimidine-2 (1H)-ketone by the aid of acid used as a catalyst, the method has the obvious advantagesthat reaction conditions are mild, the method is high in efficiency, short in time and easy to operate, only few byproducts can be generated, and the products have good colors and are high in purity;particularly, the resin D732 used as the catalyst is low in cost, easy to prepare, store and transport and good in repeatability, is easily available and is green and environmentally friendly, accordingly, the method has an excellent industrial application prospect, and the like.
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Paragraph 0014; 0015; 0016; 0018-0029; 0062-0064

(2018/10/19)

Oxidation of thiazolo[3,2-a]pyrimidin-3(2H)-ones with DMSO and Lawesson's reagent
2,2′-Dimers with a central double bond were prepared by the oxidation of 5,6-disubstituted 7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-3(2H)-ones with DMSO and Lawesson's reagent at room temperature. The role of DMSO as an oxidizing reagent was confirmed by NMR spectroscopy. The E-configuration of the central C[dbnd]C bond for the two diastereomers of compound 8m was proven by single crystal X-ray data. The dimeric thiazolopyrimidines were orange or red colored and absorption bands at 283–330 and 459–476 nm were observed in the UV spectra.
Lashmanova, Eugenia A.,Kirdyashkina, Anastasiya I.,Slepukhin, Pavel A.,Shiryaev, Andrey K.
supporting information
p. 1099 - 1103
(2018/02/19)

A Cu(II) metal-organic framework with significant H2 and CO2 storage capacity and heterogeneous catalysis for the aerobic oxidative amination of C(sp3)-H bonds and Biginelli reactions
A Cu(ii) metal-organic framework, {[Cu2(L)(H2O)2]·(5DMF)(4H2O)}n (1), has been synthesized using an angular tetracarboxylic acid ligand (H4L) incorporating both trifluoromethyl (-CF3/
Gupta, Anoop K.,De, Dinesh,Tomar, Kapil,Bharadwaj, Parimal K.
p. 1624 - 1634
(2018/02/09)

T3P-DMSO mediated one-pot tandem approach for the synthesis of 3,4-Dihydropyrimidin-2(1H)-ones/thiones from alcohols
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.
p. 241 - 245
(2018/04/20)

A reactant promoted solvent free synthesis of 3,4-dihydropyrimidin-2(1H)-thione analogues using ammonium thiocyanate
This is the first-time ammonium thiocyanate (NH4SCN) has been used as a self-promoting reactant for the synthesis of 3,4-dihydropyrimidin-2(1H)-thiones. This report describes a greener, efficient and economic protocol for one pot three-component synthesis of Biginelli compounds using various aldehydes, β-ketoesters and ammonium thiocyanate. Ammonium thiocyanate being a weak acid, accelerate the rate of reaction to obtain Biginelli compounds in solvent-free condition at 110?°C. The key advantages of the present method are high yields, short reaction time, solvent free condition, easy workup and ability to tolerate a variety of functional groups. Ammonium thiocyanate is readily available, cheaper, safer and industrial acceptable material which gives economical as well as ecological rewards to the present method.
Khatri, Chetan K.,Potadar, Santoshkumar M.,Chaturbhuj, Ganesh U.
supporting information
p. 1778 - 1780
(2017/04/13)

A Br?nsted acid catalysed enantioselective Biginelli reaction
A chiral derivative of 1,2-benzenedisulfonimide, namely (-)-4,5-dimethyl-3,6-bis(o-tolyl)-1,2-benzenedisulfonimide is herein proven to be an efficient chiral catalyst in a one pot three-component Biginelli reaction. In fact the yields of the target dihydr
Barbero, Margherita,Cadamuro, Silvano,Dughera, Stefano
p. 1529 - 1535
(2017/05/10)

1-Methyl-2-oxopyrrolidinium perchlorate ionic liquid in synthesis of 5-ethoxycarbonyl-3,4-dihydropyrimidin-2(1H)-ones
A multicomponent Biginelli reaction in a solvent-free conditions catalyzed by 1-methyl-2-oxopyrrolidinium perchlorate ionic liquid was studied. The сondensation of aromatic aldehydes, urea (thiourea), and acetoacetic ester yielded substituted 5-ethoxycarb
Badalova,Abbasov,Valiyev,Alieva,Talybov
p. 2739 - 2743
(2017/12/26)

Nanoparticles of organosilane-based NaHSO4 ionic liquid immobilized on silica as reusable heterogeneous catalyst for one-pot synthesis of 2-oxo-and thioxo-4-phenyl-1,2,3,4-tetrahydropyrimidines
Background: In spite of the fact that there are numerous reagents and methods to synthesize the dihydropyrimidinones via Biginelli reaction, but excellent yields, shorter reaction time and easy work-up are important factors which are not usually found tog
Abri, Abdolreza,Khojasteh, Mohsen Ghasemian
p. 172 - 180
(2017/06/21)

Fe+3-montmorillonite K10: As an effective and reusable catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones and –thiones
In this study, a novel, clean, convenient, appropriate and environmentally benign route to dihydropyrimidinone and thione derivatives has been developed using the reaction between various benzaldehydes, urea or thiourea, and ethyl acetoacetate in the pres
Fekri, Leila Zare,Nikpassand, Mohammad,Movaghari, Mahsa
p. 313 - 321
(2017/12/12)

An efficient and recyclable 3D printed α-Al2O3 catalyst for the multicomponent assembly of bioactive heterocycles
A catalytic methodology is reported that enables the efficient, operationally simple and environmentally friendly synthesis of diverse 1,4-dihydropyridines and 3,4-dihydropyrimidin-2(1H)-ones, including some relevant drugs and pharmacologically active derivatives. This strategy is based on the use of a 3D printed Al2O3 woodpile material that was sintered to generate a rigid structure with controlled porosity and noteworthy catalytic performance. The 3D printed Al2O3 catalyst exhibits remarkable efficacy as a Lewis acid in Biginelli and Hantzsch reactions and it can be recovered and reused ten times without any decrease in the activity. Remarkable E factors, excellent recyclability and scalability, broad substrate scope, short reaction times, excellent yields, solvent-free conditions and easy isolation procedures are key features of this methodology.
Azuaje, Jhonny,Tubío, Carmen R.,Escalante, Luz,Gómez, Mónica,Guitián, Francisco,Coelho, Alberto,Caama?o, Olga,Gil, Alvaro,Sotelo, Eddy
p. 203 - 210
(2016/12/09)

A New Type of Magnetically-Recoverable Heteropolyacid Nanocatalyst Supported on Zirconia-Encapsulated Fe3O4 Nanoparticles as a Stable and Strong Solid Acid for Multicomponent Reactions
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
p. 1551 - 1566
(2017/05/17)

Nano-ZrO2 sulfuric acid: A heterogeneous solid acid nano catalyst for Biginelli reaction under solvent free conditions
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
p. 7419 - 7425
(2016/07/13)

1,4-diazabicyclo[2.2.2]octanium diacetate: As a new, effective and reusable catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones and-thiones
In this study, a new, effective and environmentally benign procedure for the synthesis of dihydropyrimidinone and thione derivatives with various benzaldehydes, urea or thiourea, and ethyl acetoacetate in the presence of 1,4-diazabicyclo[2.2.2]octanium diacetate as a novel acidic ionic liquid, in high yield and short reaction time is reported. This method provides several advantages such as easy work-up, green, environmental friendliness and fast reaction condition along with high yields.
Fekri, Leila Zare,Movaghari, Mahsa
p. 406 - 413
(2016/10/18)

MoO2Cl2 catalyzed efficient synthesis of functionalized 3,4-dihydropyrimidin-2(1H)-ones/thiones and polyhydroquinolines: recyclability, fluorescence and biological studies
A simple, facile and efficient synthesis of functionalized dihydropyrimidinones and polyhydroquinolines using molybdenum(vi) dichloride dioxide (MoO2Cl2) has been developed. The present protocol demonstrates the exceptional tolerance
Guggilapu, Sravanthi Devi,Prajapti, Santosh Kumar,Nagarsenkar, Atulya,Lalita, Guntuku,Naidu Vegi, Ganga Modi,Babu, Bathini Nagendra
p. 838 - 843
(2016/01/12)

Organosilane sulfonated graphene oxide in the Biginelli and Biginelli-like reactions
Organosilane sulfonated graphene oxides (SSi-GO) have been synthesized by a two-step procedure involving the grafting of graphene oxide (GO) using 3-chloropropyltriethoxysilane (CCPTES) and subsequent oxidation using sulfanilic acid. It has been shown tha
Safari, Javad,Gandomi-Ravandi, Soheila,Ashiri, Samira
p. 512 - 520
(2016/01/12)

A unique opportunity for the utilization of glass wastes as a resource for catalytic applications: toward a cleaner environment
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
p. 113844 - 113858
(2016/12/24)

Cu-EDTA-modified APTMS-Fe3O4@SiO2 core-shell nanocatalyst: A novel magnetic recoverable catalyst for the Biginelli reaction
A novel copper-ethylenediamine tetracarboxylate modified core-shell magnetic catalyst is introduced. The prepared catalyst was fully characterized by various spectroscopic analyses such as XRD, SEM, FT-IR, EDX, ICP, and CHNOS. After characterization, its
Sheykhan, Mehdi,Yahyazadeh, Asieh,Rahemizadeh, Zahra
p. 34553 - 34563
(2016/05/09)

PEG-SANM nanocomposite: A new catalytic application towards clean and highly efficient Biginelli-like reaction under solvent-free conditions
A series of pyrimidinone derivatives were efficiently synthesized using PEG-SANM nanocomposite as the solid acid nanocatalyst under mild and solvent-free conditions. The generality of the process was successfully demonstrated by variation of the starting
Dalil Heirati, Seyedeh Zahra,Shirini, Farhad,Shojaei, Abdollah Fallah
p. 67072 - 67085
(2016/07/30)

Sulfated polyborate: a new and eco-friendly catalyst for one-pot multi-component synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones via Biginelli reaction
In this report, an efficient high-yield method for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones via a three-component Biginelli reaction with various aldehydes, β-ketoesters/β-diketones and urea/thiourea is described. The reaction was catalyze
Khatri, Chetan K.,Rekunge, Deelip S.,Chaturbhuj, Ganesh U.
supporting information
p. 10412 - 10417
(2016/12/07)

Calix[8]arene sulfonic acid catalyzed three-component reaction for convenient synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones under ultrasonic irradiation
In this work, the catalytic activity of calix[8]arene sulfonic acid was successfully investigated for the famous Biginelli reaction. Under ultrasonic irradiation, calix[8]arene sulfonic acid could efficiently catalyzed the three-component reaction of alde
An, Lin,Han, Li-Li,Wang, Zu-Jian,Huang, Tong-Hui,Zhu, Hui-Dong
p. 267 - 271
(2017/02/15)

Synthesis and antitumor evaluation of novel dihydropyrimidine, thiazolo [3,2-a]pyrimidine and pyrano [2,3-d]pyrimidine derivatives
A simple and efficient method has been developed for the synthesis of 4,5-dihydro-2-mercapto-4-oxo-6-substituted arylpyrimidine derivatives 2a-e and their fused rings 3b, 4b, 5b, 6b and also 1,4-dihydro-2-mercaptopyrimidine derivatives 7a-e, 9a-e using triethylamine as a catalyst. The structure of the newly synthesized compounds was confirmed on the basis of their spectral data and elemental analyses. All the synthesized compounds were evaluated for their in vitro anticancer activity against six human cancer cell lines and normal fibroblasts. Nine of the tested compounds (i.e. 2a, 2c, 2d, 3b, 4b, 5b, 8, 9a and 9c) exhibited significant cytotoxicity against most cell lines. Among these derivatives compounds 2a, 3b and 9c are the most potent, they exhibited cytotoxic effect against the six cancer cell lines with IC50 values a much lesser extent (IC50 >10,000 nM). Toxicity of the most potent compounds was measured against shrimp larvae; the results showed that compounds 2a and 3b are not toxic towards the tested organisms.
Megally Abdo, Nadia Y.
p. 168 - 180
(2015/04/22)

The Biginelli reaction under batch and continuous flow conditions: Catalysis, mechanism and antitumoral activity
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.
p. 48506 - 48515
(2015/06/16)

Cobalt manganese oxide nano catalysts as a recyclable catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones-thiones
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
p. 271 - 276
(2015/08/11)

An efficient synthesis of 3,4-Dihydropyrimidin-2(1H)-Ones and thiones catalyzed by a novel br?nsted acidic ionic liquid under solvent-free conditions
We report here an efficient and green method for Biginelli condensation reaction of aldehydes, β-ketoesters and urea or thiourea catalyzed by Br?nsted acidic ionic liquid [Btto][p-TSA] under solvent-free conditions. Compared to the classical Biginelli rea
Zhang, Yonghong,Wang, Bin,Zhang, Xiaomei,Huang, Jianbin,Liu, Chenjiang
p. 3811 - 3820
(2016/08/31)

Double catalytic effect of (PhNH3)2CuCl4in a novel, highly efficient synthesis of 2-oxo- and thioxo-1,2,3,4-tetrahydropyrimidines
An innovative route for the construction of 2-oxo- and thioxo-1,2,3,4-tetrahydropyrimidines was delineated through a multicomponent reaction under Biginelli conditions, starting from different aromatic aldehydes, β-keto esters and urea or thiourea. The pr
Jankovi, Nenad,Bugari, Zorica,Markovi, Svetlana
p. 595 - 604
(2015/08/24)

Design, synthesis, in Silico and in vitro studies of substituted 1, 2, 3, 4-Tetrahydro pyrimidine phosphorus derivatives
Molecular docking studies of the designed two series (4a-l, 6a-l, 9 and 10) of novel substituted phosphorylated 1, 4-dihydropyridine and 1,2,3,4-Tetrahydropyrimidine derivatives against the drug targets of DHFR from Bacillus cereus, LpxC from Pseudomonas aeruginosa, IDH from E. coli and MurB from Staphylococcus aureus were encouraged for their synthesis. These compounds were synthesized from substituted aromatic aldehydes, thiourea/urea and ethyl acetoacetate in the presence of polyphosphoric acid (PPA). These were further phosphorylated with diethyl (2-chloroethoxy) methyl phosphonate to get the desired products. In vitro anti-bacterial activity against the specified bacterial strains related to docked protein exhibited good inhibitory activity at different dose concentrations. Quantitative Structure Activity Relationship (QSAR) descriptors of the designed structures have demonstrated their satisfactory drug like properties. The results from Molecular Docking, QSAR descriptors and in vitro anti-bacterial activities led to the identification of safer and potential antibacterial agents of the title compounds screened. Compounds 4a, 4d, 4i, 6a, 6d, 9 and 10 were found to be potent antibacterial agents.
Babu, Kilaru Ravendra,Kumar, Yellapu Nanda,Raghavendra, Aminedi,Phanindra, Venukadasula,Madhava, Golla,Ravi, Nuchu,Bhaskar, Matcha,Raju, Chamarthi Naga
p. 862 - 871
(2015/11/17)

Preparation of iron-containing schiff base and ionic liquid based bifunctional periodic mesoporous organosilica and its application in the synthesis of 3,4-dihydropyrimidinones
A novel iron-containing Schiff base and ionic liquid based bifunctional periodic mesoporous organosilica (Fe@SBIL-BPMO) was prepared, characterized, and its catalytic application was developed. The SBIL-BPMO was first prepared by the grafting of 3-aminopr
Elhamifar, Dawood,Nazari, Elham
p. 820 - 826
(2015/05/13)

B(C6F5)3 catalyzed one-pot three-component Biginelli reaction: An efficient and environmentally benign protocol for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones
Tris(pentafluorophenyl)borane catalyzed, one-pot, simple, efficient and environmentally benign protocol for the synthesis of dihydropyrimidinones/thiones via Biginelli reaction has been described. The main highlights of the present protocol is low catalys
Prajapti, Santosh Kumar,Gupta, Keshav Kumar,Babu, Bathini Nagendra
p. 1047 - 1052
(2015/09/07)

Efficient and Green Microwave-Assisted Multicomponent Biginelli Reaction for the Synthesis of Dihydropyrimidinones Catalyzed by Heteropolyanion-Based Ionic Liquids under Solvent-Free Conditions
An efficient and green route for the synthesis of dihydropyrimidinones via microwave-assisted Biginelli reaction catalyzed by 3 mol% of heteropolyanion-based ionic liquids under solvent-free conditions has been reported. The practical reaction was found t
Fu, Renzhong,Yang, Yang,Lai, Wenchen,Ma, Yongfeng,Chen, Zhikai,Zhou, Jian,Chai, Wen,Wang, Quan,Yuan, Rongxin
supporting information
p. 477 - 487
(2015/10/29)

Boehmite nanoparticle catalyst for the one-pot multicomponent synthesis of 3,4-dihydropyrimidin-2-(1H)-ones and thiones under solvent-free conditions
A simple, green, and efficient synthesis protocol for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones using boehmite nanoparticles as catalyst was developed. It did not use any toxic metal catalysts or corrosive acidic reagents. The method gave good to excellent yields and has short reaction time, operational simplicity, and a recyclable catalyst.
Keivanloo, Ali,Mirzaee, Mahdi,Bakherad, Mohammad,Soozani, Atena
p. 362 - 367
(2014/04/03)

Bronsted acidic ionic liquid based magnetic nanoparticles: A new promoter for the Biginelli synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones
The Bronsted acidic ionic liquid 1-methyl-3-(3- trimethoxysilylpropyl) imidazolium hydrogen sulfate was immobilized on magnetic Fe3O4 nanoparticles (MNPs-IL-HSO4). The properties of the magnetic nanocatalyst were character
Safari, Javad,Zarnegar, Zohre
p. 358 - 365
(2014/01/06)

Graphite catalyzed solvent free synthesis of dihydropyrimidin-2(1H)-ones/ thiones and their antidiabetic activity
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.
p. 2897 - 2899
(2014/06/10)

Silica-bonded N-propyl sulfamic acid as an efficient recyclable catalyst for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones under heterogeneous conditions
Silica-bonded N-propyl sulfamic acid (SBNPSA) catalyzed one-pot three component Biginelli condensation of different substituted aromatic aldehydes with ethyl acetoacetate and urea/thoiurea to the respective 3,4- dihydropyrimidin-2-(1H)-ones and thiones in
Jetti, Srinivasa Rao,Bhatewara, Anjna,Kadre, Tanuja,Jain, Shubha
p. 469 - 473
(2014/03/21)

Phytic acid: A biogenic organocatalyst for one-pot Biginelli reactions to 3,4-dihydropyrimidin-2(1H)-ones/thiones
The natural organocatalyst phytic acid catalyzed one-pot Biginelli reactions by coupling β-ketoesters, aldehydes, and (thio)ureas to afford 3,4-dihydropyrimidin-2(1H)-ones/thiones. This phytic acid catalysis featured good to excellent isolated yields, sol
Zhang, Qiguo,Wang, Xin,Li, Zhenjiang,Wu, Wenzhuo,Liu, Jingjing,Wu, Hao,Cui, Saide,Guo, Kai
p. 19710 - 19715
(2014/05/20)

Ionic liquid effect over the biginelli reaction under homogeneous and heterogeneous catalysis
Bronsted and Lewis acid catalysts with ionic tags under homogeneous and heterogeneous conditions have been tested to perform the Biginelli synthesis of 3,4-dihydropyrimidin-2(1H)-one (DHPMs). Metal-containing ionic liquids were evaluated as the catalysts
Alvim, Haline G. O.,De Lima, Tatiani B.,De Oliveira, Heibbe C. B.,Gozzo, Fabio C.,De MacEdo, Julio L.,Abdelnur, Patricia V.,Silva, Wender A.,Neto, Brenno A. D.
p. 1420 - 1430
(2013/07/26)

One-pot and solvent-free synthesis of 1,4-dihydropyridines and 3,4-dihydropyrimidine-2-ones using new synthetic recyclable catalyst via Biginelli and Hantzsch reactions
Pyridine dicarboxylic acid guanidine-cobalt complex (PDAG-Co) (3) catalyzes one-pot, three-component coupling of aldehydes, b-dicarbonyl compounds, and ammonium acetate to afford the corresponding 1,4-dihydropyridines (1,4-DHPs) via Hantzsch reaction. 3,4
Shockravi, Abbas,Kamali, Mahmood,Sharifi, Negar,Nategholeslam, Mahdieh,Moghanlo, Somayeh Pahlavan
supporting information
p. 1477 - 1483
(2013/05/21)

Ultrasound-mediated synthesis of 3,4-dihydropyrimidin-2-(1H)-ones (or Thiones) with NaHSO4·H 2O
A fast and efficient Biginelli synthesis of 3,4-dihydropyrimidin-2-(1H)- ones (or thiones) by the reaction of aromatic aldehydes, β-dicarbonyls, and urea/thiourea using NaHSO4·H2O/ultrasound system is presented. The reactions were ca
Dilmaghani, Karim Akbari,Zeynizadeh, Behzad,Amirpoor, Maryam
p. 1634 - 1642
(2013/10/21)

The biginelli reaction with an imidazolium-tagged recyclable iron catalyst: Kinetics, mechanism, and antitumoral activity
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.
supporting information
p. 4156 - 4168
(2013/05/08)

Vanadatesulfuric acid: A novel, recyclable, and heterogeneous catalyst for the one-pot synthesis of dihydropyrimidinones and dihydropyrimidinthiones under solvent-free conditions
Vanadatesulfuric acid (VSA), as a novel and heterogeneous catalyst, was used for an efficient synthesis of 3,4-dihydropyrimidin-2(1H)-ones (thiones) using an aldehyde, urea, or thiourea and an acyclic β-dicarbonyl compound under solvent-free conditions. V
Nasr-Esfahani, Masoud,Abdizadeh, Tooba
p. 596 - 608
(2013/07/25)

Biginelli reaction on Fe3O4-MWCNT nanocomposite: Excellent reactivity and facile recyclability of the catalyst combined with ultrasound irradiation
A highly efficient and improved synthetic methodology for the preparation of dihydropyrimidinone derivatives using β-dicarbonyl compounds, urea/thiourea and aromatic aldehydes using Fe3O4-MWCNT as a nanocatalyst under ultrasound irra
Safari, Javad,Zarnegar, Zohre
p. 17962 - 17967
(2013/10/01)