- An appropriate one-pot synthesis of dihydropyrimidinones catalyzed by heteropoly acid supported on zeolite: An efficient and reusable catalyst for the Biginelli reaction
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A mild and efficient catalytic method has been developed for the synthesis of 3,4-dihydropyrimidin-2 (1H)-ones (DHPM) by a one-pot three-component cyclocondensation reaction using molybdophosphoric acid (MPA) supported on Y zeolite in high to excellent yi
- Moosavifar, Maryam
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- One-pot synthesis of 3,4-dihydro-2(H)-pyrimidinones catalyzed by reusable acidic choline-based ionic liquids
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A series of choline-based ionic liquids (CIL) have been synthesized in this work. The results suggested that both the cations and the anions have significant influences on their properties such as thermostabilities, acidities and their performances for the synthesis of 3,4-dihydro-2(H)-pyrimidinones. The optimized catalytic system based on the CIL [DMEA][HSO4] for the Biginelli reactions benefits from the wide substrates tolerance, benign reaction conditions, easy work-up procedures, and the feasible reusability of the ionic liquid. Graphical Abstract: The thermostabilities, acidities, and the catalytic activities for the Biginelli reactions are all follows the sequence of [DMEA][HSO4] > [Choline] [HSO4] > [DMEA][H 2PO4] > [Choline] [H2PO4][Figure not available: see fulltext.].
- Zhu, Anlian,Li, Qianqian,Li, Lingjun,Wang, Jianji
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- Selectfluor catalyzed one pot synthesis of dihydropyrimidinones: An improved protocol for the Biginelli reaction
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A novel one pot condensation of an aldehyde, β-ketoesters and urea / thiourea in acetonitrile has been performed using selectfluor in both conventional and microwave irradiation method affording dihydropyrimidinones in excellent yields (80-95%) and short
- Kumar, V. Naveen,Kumar, B. Sunil,Reddy, P. Narsimha,Reddy, Y. Thirupathi,Rajitha
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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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- 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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- Biginelli reaction on Fe3O4-MWCNT nanocomposite: Excellent reactivity and facile recyclability of the catalyst combined with ultrasound irradiation
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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
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- An efficient one-pot synthesis of 3,4-dihydropyrimidin-2-ones catalyzed by methanesulfonic acid
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An efficient synthesis of 3,4-dihydropyrimidin-2-ones (DHPMs) from the aldehydes, β-ketoesters, and urea in ethanol using methanesulfonic acid (CH3SO3H) as the catalyst is described. Compared with the classical Biginelli reaction con
- Jin, Tong-Shou,Wang, Huan-Xin,Xing, Chun-Yong,Li, Xiao-Liu,Li, Tong-Shuang
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- Pyridinium-based bronsted acidic ionic liquid as a highly efficient catalyst for one-pot synthesis of dihydropyrimidinones
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In this work, the synthesis and characterization of 3-carboxypyridinium hydrogensulfate ([Hcpy]HSO4) as a new Brnsted acidic ionic liquid are reported. This reusable, inexpensive, and green catalyst was employed for one-pot condensation of 1,3-
- Hajipour, Abdol R.,Seddighi, Mohadeseh
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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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- One-pot, green and efficient synthesis of 3,4-dihydropyrimidin-2(1H)-ones or thiones catalyzed by citric acid
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One-pot three-component condensation of ethyl acetoacetate, aldehyde and urea or thiourea in refluxing ethanol in the presence of catalytic amounts of citric acid afforded the corresponding 3,4-dihydropyrimidin- 2(1H)-ones/thiones in high yields. The cata
- Ghorbani-Choghamarani, Arash,Taghipour, Tahereh,Azadi, Gouhar
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- Bronsted acidic ionic liquid-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1h)-ones and thiones under solvent-free conditions
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An efficient and convenient procedure for the synthesis of 3,4-dihydropyrimidin- 2(1H)-ones and thiones by condensation of ethylacetoacetate, aldehydes, and urea or thiourea in the presence of methylimidazolium hydrogensulfate is described. Aromatic and a
- Hajipour, Abdol R.,Khazdooz, Leila,Zarei, Amin
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- Silica sulfuric acid: An efficient and reusable catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones
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Silica sulfuric acid efficiently catalyzes the three-component Biginelli reaction between an aldehyde, a β-dicarbonyl compound and urea or thiourea in refluxing ethanol to afford the corresponding dihydropyrimidinones in high yields. The catalyst is reusa
- Salehi, Peyman,Dabiri, Minoo,Zolfigol, Mohammad Ali,Bodaghi Fard, Mohammad Ali
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- Synthesis of 3,4-dihydropyrimidin-2(1H)-ones Using Ce(SO4) 2-SiO2 as a heterogeneous and recyclable catalyst
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A simple and efficient synthesis of 3,4-dihydropyrimidinones or thiones is described, using silica-supported ceric sulfate [Ce(SO4) 2-SiO2] as a heterogeneous catalyst from an aldehyde, 1,3-dicarbonyl compound, and urea or
- Pei, Wen,Wang, Qin
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- Imidazolium-based phosphinite ionic liquid as reusable catalyst and solvent for one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-(thio)ones
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A mild and efficient procedure for the synthesis of 3,4-dihydropyrimidin- 2(1H)-(thio)ones in phosphinite ionic liquid is described. This ionic liquid plays a dual role as both the reaction media and also a catalyst, which can be easily recovered and reus
- Valizadeh, Hassan,Shockravi, Abbas
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- 1,3-Disulfonic acid benzimidazolium chloride as an efficient and recyclable ionic liquid catalyst for the synthesis of 3,4-dihydropyrimidine-2-(1H)-ones/thiones
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1,3-Disulfonic acid benzimidazolium chloride ionic liquid ([Dsbim]Cl) was prepared, characterized and applied as an efficient, homogeneous and recyclable catalyst for the synthesis of 3,4-dihydropyrimidine-2-(1H)-ones/thiones through the one-pot three-com
- Abbasi, Mohsen
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- Cellulose sulfuric acid: An efficient biodegradable and recyclable solid acid catalyst for the one-pot synthesis of 3,4-dihydropyrimidine-2(1H)-ones
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Biosupported cellulose sulfuric acid has been found to be an efficient solid acid catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2(1H)- ones. The advantages of this method are avoidance of harsh reaction conditions, ecofriendly chemistry, oper
- Reddy, P. Narsimha,Reddy, Y. Thirupathi,Reddy, M. Nikhil,Rajitha,Crooks, Peter A.
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- A highly efficient one-pot multicomponent synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones catalyzed by strontium pyroarsenate nano-plates
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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
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- One-pot synthesis of dihydropyrimidiones catalyzed by strontium(II) triflate under solvent-free conditions
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A simple, efficient and practical procedure for the Biginelli reaction using strontium(II) triflate [Sr(OTf)2] as a novel catalyst is described under solvent-free conditions in high yields. The catalyst exhibited remarkable reactivity and it is
- Su, Weike,Li, Jianjun,Zheng, Zhiguo,Shen, Yinchu
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- Fe+3-montmorillonite K10: As an effective and reusable catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones and –thiones
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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
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- Combined Role of the Asymmetric Counteranion-Directed Catalysis (ACDC) and Ionic Liquid Effect for the Enantioselective Biginelli Multicomponent Reaction
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This work describes new chiral task-specific ionic liquids bearing chiral anions as the catalysts for the enantioselective multicomponent Biginelli reaction. For the first time, the combined role of asymmetric counteranion-directed catalysis (ACDC) and io
- Alvim, Haline G. O.,Pinheiro, Danielle L. J.,Carvalho-Silva, Valter H.,Fioramonte, Mariana,Gozzo, Fabio C.,Da Silva, Wender A.,Amarante, Giovanni W.,Neto, Brenno A. D.
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- Separation of enantiomers of 4-aryldihydropyrimidines by direct enantioselective HPLC. A critical comparison of chiral stationary phases
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The separation of the enantiomers of 29 racemic 4-aryldihydropyrimidine-5-carboxylates (DHPMs), aza-analogs of nifedipine-type dihydropyridine calcium channel modulators, was evaluated in direct enantioselective HPLC, employing the following commercially available chiral stationary phases (CSPs): Chiralcel OD-H, ChiraDex, Chirobiotic V and T, and Whelk-O1. In addition, a 1,2-diphenyl-1,2-diaminoethane based CSP and two quinine carbamate based chiral ion exchangers were also employed. For all 29 DHPMs separation of individual, enantiomers could be achieved with at least one CSP with α-values ranging from 1.10 to 8.67.
- Kleidernigg, Oliver P.,Kappe, C. Oliver
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- Silica immobilized nickel complex: An efficient and reusable catalyst for microwave-assisted one-pot synthesis of dihydropyrimidinones
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Dihydropyrimidinones (DHPM's) have been prepared by one-pot condensation of aldehydes, urea and 1,3-dicarbonyl compounds in presence of covalently anchored nickel complex on silica as catalyst in microwave under solvent-free conditions. The prepared catal
- Sharma,Rawat, Deepti
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- N-Sulfonic acid poly(4-vinylpyridinium) chloride as a highly efficient and reusable catalyst for the Biginelli reaction
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A mild, simple and efficient procedure for the preparation of 3,4-dihydropyrimidin-2(1H)-ones and -thiones is described using N-sulfonic acid poly(4-vinylpyridinium) chloride (NSPVPC) as a heterogeneous and efficient catalyst under solvent-free conditions
- Shirini, Frahad,Abedini, Masoumeh,Pourhasan-Kisomi, Reyhaneh
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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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- Oxalic acid as a versatile catalyst for one pot facile synthesis of 3,4-dihydropyrimidin-2-(1H)-ones and their thione analogues
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(Chemical Equation Presented) 3,4-Dihydropyrirnidin-2-(1H)-ones and their thione analogues are synthesized from the condensation of aromatic aldehydes, β-dicarbonyl compound and urea or thiourea in presence of 5 mol% of oxalic acid in ethanol-water (1:2 ;
- Sangshetti, Jaiprakash N.,Kokare, Nagnnath D.,Shinde, Devanand B.
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- Efficient and green synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones using imidazol-1-yl-acetic acid as a novel, reusable and water-soluble organocatalyst
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A practical and green chemistry route to the Biginelli multicomponent cyclocondensation reaction using imidazol-1-yl-acetic acid as a novel bifunctional and efficient organocatalyst is described under two different sets of reaction conditions.
- Kargar, Mojgan,Hekmatshoar, Rahim,Mostashari, Abdoljalil,Hashemi, Zahra
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- One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones catalyzed by SO3H@imineZCMNPs as a novel, efficient and reusable acidic nanocatalyst under solvent-free conditions
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The synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives was accomplished efficiently via a three-component reaction between ethyl acetoacetate, various types of aldehydes, and urea in the presence of 10 mg SO3H@imineZCMNPs as a novel, envir
- Abbaspour-Gilandeh, Esmayeel,Yahyazadeh, Asieh,Aghaei-Hashjin, Mehraneh
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- Efficient one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones catalyzed by a new heterogeneous catalyst based on Co-functionalized Na+-montmorillonite
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In the present study, we report a simple, facile and efficient solvent-free protocol for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones by the three component condensation of aldehyde, ethyl acetoacetate and urea through using Co@imine-Na+-MM
- Khorshidi, Alireza,Tabatabaeian, Khalil,Azizi, Hashem,Aghaei-Hashjin, Mehraneh,Abbaspour-Gilandeh, Esmayeel
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- Tungsten-substituted molybdophosphoric acid impregnated with kaolin: effective catalysts for the synthesis of 3,4-dihydropyrimidin-2(1: H)-ones v i a biginelli reaction
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A series of highly reusable heterogeneous catalysts (10-25 wt% PMo7W5/kaolin), consisting of tungsten-substituted molybdophosphoric acid, H3PMo7W5O40·24H2O (PMo7W5) impregnated with acid treated kaolin clay was synthesized by the wetness impregnation meth
- Aher, Dipak S.,Khillare, Kiran R.,Chavan, Laxmikant D.,Shankarwar, Sunil G.
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- Crosslinked poly(ionic liquid) as high loaded dual acidic organocatalyst
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A dual acidic heterogeneous organocatalyst was synthesized by copolymerization of acidic ionic liquid monomer (vinyl-3-(3-sulfopropyl) imidazolium hydrogen sulfate [VSim][HSO4]) and ionic liquid crosslinker (1,4-butanediyl-3,3′-bis-l-vinyl imid
- Pourjavadi, Ali,Hosseini, Seyed Hassan,Soleyman, Rouhollah
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- A green synthesis of 3,4-dihydropyrimidine-2(1H)-one/thione derivatives using nanosilica-supported tin(II) chloride as a heterogeneous nanocatalyst
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Efficient, green, and straightforward synthesis of 3,4-dihydropyrimidine- 2(1H)-one/thione derivatives under favorable conditions has been achieved by reaction of urea/thiourea, aldehydes, and ethyl acetoacetate, using the synthetic potential of nanosilic
- Safaei Ghomi, Javad,Teymuri, Raheleh,Ziarati, Abolfazl
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- 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
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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
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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)
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- Synthesis of dihydropyrimidin-2-one/thione library and cytotoxic activity against the human U138-MG and Rat C6 glioma cell lines
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Two series of 4-aryl-3,4-dihydropyrimidin-2(1H)-(thio)ones including monastrol (1a), have been synthesized by an environment-friendly methodology based on the combined use of citric acid or oxalic acid and TEOF (triethylorthoformate). The library was eval
- Canto, Ro?mulo F.S.,Bernardi, Andressa,Battastini, Ana Maria O.,Russowsky, Dennis,Eifler-Lima, Vera Lucia
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- Highly convenient one-pot conversion of aryl acyals or aryl aldehyde bisulfites into dihydropyrimidones using Bi(NO3)3· 5H2O
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A new, facile, and efficient one-pot deprotection-cyclocondensation method is presented for the Biginelli reaction from aryl acylals or aryl aldehyde bisulfites in the presence of catalytic amounts of Bi(NO3) 3·5H2O under
- Khosropour, Ahmad R.,Khodaei, Mohammad M.,Beygzadeh, Mojtaba
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- Synthesis of 3,4-dihydropyrimidin-2(1H)-ones catalyzed by nafion-H under ultrasound irradiation and solvent-free conditions
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A novel synthesis of 3,4-dihydropyrimidin-2-(1H)-ones by one-pot cyclocondensation of aldehydes, 1,3-dicarbonyl compounds and urea or thiourea using nafion-H as the catalyst under ultrasound irradiation and solvent-free conditions was developed. Compared
- Wang,Pei
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- A green approach to the synthesis of 2,3-dihydropyrimidin-2(1H)-ones by uronium hydrogensulfate under solvent-free conditions
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3,4-Dihydropyrimidin-2(1H)-ones and -thiones are synthesized in high yields by a one-pot condensation of an aldehyde, a β-dicarbonyl compound with hydrogensulfate salt of urea or thiourea under solvent-free conditions.
- Salehi, Peyman,Dabiri, Minoo,Zolfigol, Mohammad Ali,Baghbanzadeh, Mostafa
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- An efficient, high yield protocol for the one-pot synthesis of dihydropyrimidin-2(1H)-ones catalyzed by iodine
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The use of iodine, as a catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones is reported. The use of iodine, as a catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones is reported.
- Bhosale, Rajesh S.,Bhosale, Sidhanath V.,Bhosale, Sheshanath V.,Wang, Tianyu,Zubaidha
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- Ionic liquid effect over the biginelli reaction under homogeneous and heterogeneous catalysis
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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.
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- Dowex-promoted general synthesis of N,N′-disubstituted-4-aryl-3,4-dihydropyrimidinones using a solvent-free Biginelli condensation protocol
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Dowex-50W ion exchange resin-promoted solvent-free heating of an intimate mixture of an aldehyde, an active methylene compound and N,N′-dimethylurea furnished the title compounds in moderate to good yields.
- Singh, Kamaljit,Arora, Divya,Singh, Sukhdeep
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- One-pot construction of dihydropyrimidinones in ionic liquids
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The use of the ionic liquid [bmim]Cl·2AlCl3 for the preparation of dihydropyrimidinones is described.
- Bahekar, Sushilkumar S.,Kotharkar, Sandip A.,Shinde, Devanand B.
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- A one-pot synthesis of 3,4-dihydropyrimidin-2-(IH)-onesfrom primary alcohols promoted by Bi(NO3)3.5H2O in two different media: Organic solvent and ionic liquid
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A new, simple and efficient procedure for the one-pot conversion of alcohols instead of aldehydes to the corresponding 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) with Bi(NO3)3.5H2O as a commercially available, inexpensive, st
- Khosropour, Ahmad R.,Khodaei, Mohammd M.,Beygzadch, Mojtaba,Jokar, Mahbubeh
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- Microwave-induced perchloric acid catalyzed novel solvent-free synthesis of 4-aryl-3,4-dihydropyrimidones via biginelli condensation
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(Chemical Equation Presented) We report here domestic microwave-induced perchloric acid-catalyzed solvent-free synthesis of various 4-aryl-3,4- dihydropyrimidones for the first time. In all the cases the yields are excellent and the mechanism follows a si
- Mukhopadhyay, Chhanda,Datta, Arup,Banik, Bimal K.
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- Titanium(IV) chloride catalyzed one-pot synthesis of 3,4-dihydropyrimidin- 2(1H)-ones and thiones
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Titanium(IV) chloride catalyses efficiently the three-component condensation reaction of an aldehyde, 1,3-dicarbonyl compound and urea or thiourea to afford the corresponding 3,4-dihydropyrimidin-2(1H)-ones and thiones in high yields.
- Nagawade, Rahul R.,Kotharkar, Sandeep A.,Shinde, Devanand B.
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- Synthesis of tetrahydrobenzo[b]pyran and 3,4-dihydropyrimidinone derivatives using glutamic acid as an efficient catalyst
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The efforts to use green catalysts for organic synthesis are undeniable. Natural catalysts are biodegradable and easy to access. Herein, glutamic acid was applied as a natural and green catalyst for the synthesis of tetrahydrobenzo[b]pyran and 3,4-dihydro
- Khandan-Barani, Khatereh,Kangani, Mehrnoosh,Mirbaluchzehi, Maryam,Siroos, Zahra
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- Glycerin and [Iron(III)(salen)]Cl as an efficient catalytic medium for multicomponent reactions
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In this investigation, glycerol and [Fe(III)(salen)]Cl as a green catalyst system were used in multicomponent reactions for the synthesis of bis(indolyl)methanes, 3,4-dihydropyrimidinones, and 1,4-dihydropyridines, respectively. Excellent product yields and short reaction times were achieved.
- Seyedi, Neda
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- A one pot green synthesis of 3,4 dihydropyrimidin-2-(1H)-ones/thiones catalyzed by MgO-ZrO2 under solvent-free conditions
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An efficient green synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones (DHPMs) using MgO/ZrO2 as heterogeneous basic catalyst from an aldehyde, β-keto ester and urea/thiourea under solvent-free conditions is described. A variety of aldehydes
- Gawande, Manoj B.,Nagrik, Deepak M.,Ambhore, Damodar M.
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- General solvent-free ionic liquid catalyzed C-N/C-C coupled cyclization to diverse dihydropyrimidinones and new organic materials: Langmuir-Blodgett film study
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An ionic liquid catalyzed dual C-N/C-C coupled cyclization of a three component assembly is demonstrated to access 3,4-dihydropyrimidin-2(1H)-one (DHPM) analogues under solvent-free green conditions. Innovative new organic materials are introduced with pu
- Majumdar, Swapan,De, Jhinuk,Pal, Ajitesh,Ghosh, Indra,Nath, Ranendu K.,Chowdhury, Sandip,Roy, Dipanwita,Maiti, Dilip K.
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- Novel and Efficient Synthesis of DHPMs Catalyzed by di-DACH-Pyridylamide Ligands
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Di-DACH-pyridylamide ligands, symmetrical bridged bis-Schiff base, and spiro pyrrolizines as catalysts in the synthesis of dihydropyrimidinethiones (DHPMs) using the Biginelli reaction is first reported. This new protocol has the advantages of environment
- Song, Qingbao,An, Xiaoxia,Che, Fengfeng,Shen, Tianhua
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- Water-tolerant and reusable lewis acid catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2-(1h)- ones under solvent-free conditions
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3,4-Dihydropyrimidin-2-(1H)-ones were synthesized in high yields by a one-pot cyclocondensation of an aldehyde, a 1,3-dicarbonyl compound, and urea using copper methanesulfonate (2 mol %) as a recyclable catalyst under solvent-free conditions in short rea
- Wang, Min,Song, Zhiguo,Jiang, Heng,Gong, Hong
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- Eosin Y photocatalyzed access to Biginelli reaction using primary alcohols via domino multicomponent cascade: an approach towards sustainable synthesis of 3,4-dihydropyrimidin-2(1H)-ones
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The Eosin Y photocatalyzed Biginelli protocol has been established by a cascade one-pot three-component reaction of primary alcohols, α-ketoester, and urea to provide pharmacologically promising 3,4-dihydropyrimidin-2(1H)-ones in high yields. The key benefits of the present scheme are the capability to allow operational simplicity, readily available substrates, straightforward workup and high yields. This Eosin Y based photocatalytic approach can permit conquering traditional metal-catalyzed reactions in a sustainable manner, thus delivering economic and environmental rewards. Graphical abstract: An environmentally benign protocol for the synthesis of 3,4-DHPMs has been developed using inexpensive molecular oxygen, visible light as green energy source and eosin Y as photoreceptor-cum-sensitizer. The utilized photoreceptor revealed its unique properties in rapid intersystem crossing, high photo and chemical stability, ease of separation and high catalytic efficiency.[Figure not available: see fulltext.].
- Bhargava, Gaurav,Kumar, Gobind,Kumar, Rupesh,Kumar, Yogesh
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- Magnetic Silica-Coated Picolylamine Copper Complex [Fe3O4@SiO2@GP/Picolylamine-Cu(II)]-Catalyzed Biginelli Annulation Reaction
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An efficient and heterogeneous novel magnetic silica-coated picolylaminecopper complex [Fe3O4@SiO2@GP/Picolylamine-Cu(II)] was synthesized, characterized, and employed as a magnetically recoverable nanocatalyst in Biginelli condensation for the preparatio
- Rezayati, Sobhan,Kalantari, Fatemeh,Ramazani, Ali,Sajjadifar, Sami,Aghahosseini, Hamideh,Rezaei, Aram
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p. 992 - 1010
(2022/01/11)
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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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- RETRACTED ARTICLE: Boric acid in magnetized water: Clean and powerful media for synthesis of 3,4-dihydropyrimidin-2(1: H)-ones
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Water was magnetized via an external magnetic field and employed, for the first time, as a solvent in green preparation of 3,4-dihydropyrimidin-2(1H)-ones by the one-pot three-component condensation reaction using boric acid as a catalyst. Shorter reactio
- Khakyzadeh, Vahid,Moosavi-Zare, Ahmad Reza,Sheikhaleslami, Sahra,Ehsani, Amir,Sediqi, Salbin,Rezaei-Gohar, Mohammad,Jalilian, Zahra
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p. 22751 - 22755
(2021/07/21)
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- CoFe2O4?SiO2-NH2-CoII NPs: An effective magnetically recoverable catalyst for Biginelli reaction
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Biginelli reaction entails acid-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) with simply-accessible initial substances, specifically, aldehyde, urea, and active methylene compound. DHPMs have stimulated a resurgence of attention in the previous two decades because of their broad-ranging pharmacological actions and the existence of varied all-natural products. Currently, green methods to asymmetric Biginelli reaction have been researched for anti-inflammatory DHPMs. In materials chemistry, DHPMs are increasingly decision applications in the creation of materials like polymers, adhesives, fabric dyes, etc. In light of the simplicity by which the Biginelli reaction is conducted, numerous interesting prospects expect its exploitation in variety fields. CoFe2O4?SiO2-NH2-CoII is herein turned out to be an effective catalyst at a three-component Biginelli reaction. The yield of the corresponding DHPMs was rather large (20 cases; average 92 percent). Finally, we herein suggest a procedure that shows lots of advantages and benefits such as the whole lack of solvents, mild reaction conditions, comparatively short reaction times. Also, CoFe2O4?SiO2-NH2-CoII NPs catalyst has been readily recovered from the reaction combination and reused, without the decrease of catalytic action.
- Allahresani, Ali,Hemmat, Kaveh,Nasseri, Mohammad Ali,Sangani, Mehri Mohammadpour
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- Synthesis and characterization of the immobilized polythiophene on magnetic carbon nanotube as a prominent catalyst for the synthesis of dihydropyrimidinone and octahydroquinazolinone derivatives
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Abstract: In this work, the immobilized polythiophene on magnetic carbon nanotube (CNT–Fe3O4–PTh) was synthesized and introduced as a novel and recoverable catalytic system. The prepared magnetic heterogeneous nanocatalyst was characterized by FT-IR, TGA, EDX, VSM, XRD, TEM, and FE-SEM. Next, the catalytic efficiency of CNT–Fe3O4–PTh was evaluated through the green synthesis of a variety of dihydropyrimidinone and octahydroquinazolinone through Biginelli reaction between aromatic aldehydes, urea/thiourea, and β-dicarbonyl compounds under solvent-free conditions. The catalyst was magnetically recovered and recycled for five cycles without a discernible loss in its catalytic activity. Simple workup, affordability, short reaction times, mild reaction conditions, and the high yield of products are the interesting features of this project. Graphic abstract: An environmentally benign nanocomposite was prepared using carbon nanotube as an inexpensive, nontoxic, and stable support in the preparation of CNT–Fe3O4–PTh, which was efficiently used as catalyst for the green synthesis of dihydropyrimidinone and octahydroquinazolinone derivatives through Biginelli reaction under solvent-free conditions.[Figure not available: see fulltext.].
- Akbarzadeh, Parisa,Koukabi, Nadiya
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p. 4955 - 4969
(2020/08/19)
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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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- 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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- BiCl3-modified perlite as an effective catalyst for selective organic transformations: a green protocol
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A new perlite supported Bismuth Chloride (BiCl3) was used as an efficient heterogeneous catalyst for the synthesis of heterocyclic compounds viz., quinoxalines and dihydropyrimidinones. Fourier-transform infrared spectroscopy (FT–IR), scanning
- Brindha, Kannan,Amutha, Parasuraman,Krishnakumar, Balu,do Nascimento Sobral, Abílio José Fraga
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p. 4367 - 4381
(2019/05/15)
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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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- 2-oxo-1,2,3,4-tetrahydropyrimidines ethyl esters as potent β-glucuronidase inhibitors: One-pot synthesis, in vitro and in silico studies
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Background: Glucuronidation is essential for the metabolism and excretion of toxic substances. β-Glucuronidase enzyme slows down the process of glucuronidation, and thus plays an important role in the on-set of colorectal carcinoma, and many other disease
- Iqbal, Sarosh,Shaikh, Nimra N.,Khan, Khalid M.,Naz, Sehrish,Ul-Haq, Zaheer,Perveen, Shahnaz,Choudhary, Muhammad I.
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p. 818 - 830
(2018/11/30)
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- A 3, 4 - dihydro pyrimidone/thioketone of heterocyclic compound synthetic method
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The present invention belongs to the technical field of organic synthesis, and discloses a synthesis method of a 3,4-dihydropyrimidin/thinatoheterocyclic compound. According to the synthesis method, an xylose acid is used as a catalyst to catalyze a reaction among aromatic aldehyde, a beta-carbonyl compound and urea or thiourea, thereby producing the 3,4-dihydropyrimidin/thinatoheterocyclic compound. According to the synthesis method provided by the prevent invention, the xylose acid is used as the catalyst, and the reaction is performed without a solvent. The method has advantages of being high in availability of raw materials, simple in process, mild in reaction condition, high in yield, and green and environmentally friendly. Furthermore, the synthesis method provided by the prevent invention is wide in substrate applicability, can synthesize a plurality of 3,4-dihydropyrimidin/thinatoheterocyclic compounds by using different substrates, and has a wide application prospect.
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Paragraph 0020; 0031-0033
(2017/12/29)
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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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- 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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- Towards Enzyme-like, Sustainable Catalysis: Switchable, Highly Efficient Asymmetric Synthesis of Enantiopure Biginelli Dihydropyrimidinones or Hexahydropyrimidinones
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Organocatalysts displaying a network of cooperative hydrogen bonds (NCHB) have been employed in an enzyme-like manner for a direct, switchable synthesis of enantiopure hexahydropyrimidinones (HHPMs) or dihydropyrimidinones (DHPMs), which starts at a common, easily accessible α-ureidosulfone stage. The NCHB organocatalyst exploits all its potential as a pure hydrogen-bond biomimetic catalyst even in the presence of organic bases. This one-pot, diastereo- and enantioselective synthetic procedure has been proven to be robust, scalable, highly efficient, and environmentally benign. A straightforward and truly practical entry to enantiopure HHPMs is reported for the first time.
- Lillo,Saá
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p. 17182 - 17186
(2016/11/23)
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- 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
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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
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p. 406 - 413
(2016/10/18)
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- Solid-Supported Synthesis of Flexible Dimeric Pyridinium Salts and Their Catalytic Activities
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The synthesis of flexible dimeric pyridinium ionic liquids by both conventional and solid-supported approaches are described. We have optimized the Biginelli reaction with various concentrations of our synthesized ionic liquids with various counter ions.
- Manikandan, Chitrarasu,Ganesan, Kilivelu
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supporting information
p. 1527 - 1530
(2016/06/14)
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- PEG-SANM nanocomposite: A new catalytic application towards clean and highly efficient Biginelli-like reaction under solvent-free conditions
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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
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p. 67072 - 67085
(2016/07/30)
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- Organosilane sulfonated graphene oxide in the Biginelli and Biginelli-like reactions
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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
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p. 512 - 520
(2016/01/12)
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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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- Double catalytic effect of (PhNH3)2CuCl4in a novel, highly efficient synthesis of 2-oxo- and thioxo-1,2,3,4-tetrahydropyrimidines
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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
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p. 595 - 604
(2015/08/24)
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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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- Design, synthesis, in Silico and in vitro studies of substituted 1, 2, 3, 4-Tetrahydro pyrimidine phosphorus derivatives
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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
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p. 862 - 871
(2015/11/17)
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- Solvent-free efficient one-pot synthesis of Biginelli and Hantzsch compounds catalyzed by potassium phthalimide as a green and reusable organocatalyst
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The usage of potassium phthalimide (PPI) for the simple and green one-step multicomponent synthesis of Hantzsch 1,4-dihydropyridines, polyhydroquinolines, 3,4-dihydropyrimidin-2(1H)-ones/thiones, and octahydroquinazolinones under solventless conditions at 120°C is reported. The method is operationally simple, environmentally benign, and has relatively high yields. The other merits of this method include efficient, clean, green, and catalyst reusability.
- Kiyani, Hamzeh,Ghiasi, Maryam
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p. 5177 - 5203
(2015/07/08)
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- Bronsted acidic ionic liquid based magnetic nanoparticles: A new promoter for the Biginelli synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones
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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
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p. 358 - 365
(2014/01/06)
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- Sulphated silica tungstic acid as a highly efficient and recyclable solid acid catalyst for the synthesis of tetrahydropyrimidines and dihydropyrimidines
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For the first time sulphated silica tungstic acid (SSTA) has been synthesized and used as an acidic catalyst in organic synthesis. The catalyst was prepared by a simple method based on the reaction of silica with SOCl 2 followed by addition of
- Ahmed, Nayeem,Siddiqui, Zeba N.
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- 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
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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
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p. 469 - 473
(2014/03/21)
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- Efficient and green catalytic synthesis of dihydropyrimidinone (thione) derivatives using cobalt nitrate in solvent-free conditions
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A series of 3,4-dihydropyrimidin-2(1H)-one(thione) derivatives was synthesized using Co(NO3)2.6H2O in solvent-free condition. Avoiding organic solvents during the chemical reactions leading to an economic approach is effective. The reaction is characteriz
- Nasr-Esfahani, Masoud,Montazerozohori, Morteza,Aghel-Mirrezaee, Maryam,Kashi, Hassan
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p. 2311 - 2314
(2014/07/22)
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- Development and efficient 1-glycyl-3-methyl imidazolium chloride-copper(II) complex catalyzed highly enantioselective synthesis of 3, 4-dihydropyrimidin- 2(1H)-ones
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A novel, effective asymmetric 1-glycyl-3-methyl imidazolium chloride-copper(II) complex [[Gmim]Cl-Cu(II)] was synthesized and studied as organocatalyst for enantioselective Biginelli reaction under solvent free condition at 25°C. The hydrophobic group on
- Karthikeyan, Parasuraman,Aswar, Sachin Arunrao,Muskawar, Prashant Narayan,Bhagat, Pundlik Rambhau,Senthil Kumar
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p. 154 - 162
(2013/02/23)
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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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