- A new imidazole-functionalized 3D-cobalt metal-organic framework as a high efficiency heterogeneous catalyst for Knoevenagel condensation reaction of furfural
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We have synthesized a new 3D Co(Ⅱ) based metal-organic framework [Co(pytpy)(AIP)·H2O]n(1)(C2/c)(pytpy = 4’-(4-pyridyl)-4,2’:6′,4″-terpyridine,AIP = 5-aminoisophthalic acid) by solvothermal method. Its crystal structure was determined
- Feng, Lixi,Gu, Wen,Liu, Xin,Liu, Zhida,Ning, Liangmin,Wang, Kaiyuan
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- A bi-functional 3D PbII–organic framework for Knoevenagel condensation reaction and highly selective luminescent sensing of Cr2O7 2?
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A novel 3D PbII–organic framework {Pb(AIA)2}n (denoted as 1) can be successfully constructed by the assembly of 5-aminonicotinic acid (HAIA) and PbII cation under hydrothermal condition. The prepared 1 can be in
- Miao, Chaolin
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- A mononuclear Cu(II)-based metal-organic framework as an efficient heterogeneous catalyst for chemical transformation of CO2 and Knoevenagel condensation reaction
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A novel 2D Cu(II) metal-organic framework, [(Cu(L)2·(H2O)2·(NO3)2]n (namely 1), can be synthesized by the self-assemble of 4-(5-methyl-3-pyridine)-1,2,4-triazole (namely L) and Cu(II) ion.
- Guo, Feng
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- A novel 3D MOF with rich lewis basic sites as a base catalysis toward knoevenagel condensation reaction
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A novel 3D MOF with high stability, {[Eu(TATMA)(H2O)·2H2O}n (namely 1), was solvothermally synthesized by a semi-rigid organic ligand 4,4,4″-s-triazine-1,3,5-triyltri-m-aminobenzoic acid (denoted as H3TATMA) and
- Zhao, Shixia
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- Two 3D Metal-Organic Frameworks Based on CoII and ZnII Clusters for Knoevenagel Condensation Reaction and Highly Selective Luminescence Sensing
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Two metal-organic frameworks (MOFs) with 3D structures, {[Co24(BDPO)12(H2O)12]·18DMF·40H2O}n (1) and {[NH2(CH3)2]4[Zn3(HBDPO)2/s
- He, Hongming,Zhu, Qian-Qian,Sun, Fuxing,Zhu, Guangshan
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- A highly stable 3D metal?organic framework for selectively luminescent sensing and knoevenagel condensation reaction
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A 3D metal?organic framework with excellent stability based on ZnII and a neutral linker (namely L), {[ZnL(H2O)]?2NO3?2DEF}n (namely 1), has been constructed under the commonly solvothermal condition. The as-syn
- Guo, Feng,Su, Changhua,Chu, Zepeng,Zhao, Minghui
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- Two PbII-based coordination polymers based on 5-aminonicotinic acid and 5-hydroxynicotinic acid for Knoevenagel condensation reaction and luminescent sensor
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Two new PbII-based coordination polymers based on 5-aminonicotinic acid (namely HL–NH2) and 5-hydroxynicotinic acid (namely HL–OH) are both successfully synthesized under solvothermal synthesis conditions. PbCl2 and HL-NH
- Zhang, Xiuling,Zhang, Ranhui,Jin, Yaoqiang,Li, Tingting
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Read Online
- Nanochannel-based {BaZn}-organic framework for catalytic activity on the cycloaddition reaction of epoxides with CO2and deacetalization-Knoevenagel condensation
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Herein, the rare combination of BaII (5s) and ZnII (3d) in the presence of the structure-oriented TDP6- ligand generated the nanochannel-based hybrid material {[(CH3)2NH2]2[BaZn(TDP)(H2O)]·DMF·5H2O}n (NUC-51, H6TDP = 2,4,6-tri(2,4-dicarboxyphenyl)pyridine), which possesses excellent physicochemical characteristics such as nanoscopic channels, high porosity, large specific surface area, and high heat/water-resistance. To the best of our knowledge, this is the first 3D [BaIIZnII(CO2)6(H2O)]-based nano-porous host framework, whose activated state possesses the coexistence of Lewis acid-base sites including 4-coordinated Zn2+ ions, 7-coordinated Ba2+ ions, uncoordinated carboxyl oxygen atoms, and Npyridine atoms. Catalytic experiments exhibited that activated NUC-51a possesses a high catalytic activity on the cycloaddition reactions of epoxides with CO2 at 55 °C, which can be ascribed to its structural advantages of nanoscale channels and rich bifunctional active sites. Moreover, NUC-51a could significantly accelerate the deacetalization-Knoevenagel condensation reaction in DMSO solvent at 70 °C.
- Chen, Hongtai,Fan, Liming,Gao, Yanpeng,Lv, Hongxiao,Zhang, Xiutang
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p. 3546 - 3556
(2022/03/14)
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- Kinetically Controllable Pd-Catalyzed Decarboxylation Enabled [5 + 2] and [3 + 2] Cycloaddition toward Carbocycles Featuring Quaternary Carbons
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A decarboxylative protocol has been developed toward a range of carbocycles. The key success is based on the use of a batch of newly designed cyclic carbonates as substrates that can provide carbon-carbon zwitterion intermediate under palladium catalysis.
- Yan, Biwei,Zuo, Linhong,Chang, Xiaowei,Liu, Teng,Cui, Manying,Liu, Yang,Sun, Haiyu,Chen, Weipeng,Guo, Wusheng
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supporting information
p. 351 - 357
(2021/01/26)
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- Synthesis of 5H-indeno[1,2-b]pyridine derivatives: Antiproliferative and antimetastatic activities against two human prostate cancer cell lines
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This study describes the direct synthesis of 2-amino-4-(phenylsubstituted)-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives 5–21, through sequential multicomponent reaction of aromatic aldehydes, malononitrile, and 1-indanone in the presence of ammonium acetate and acetic acid (catalytic). The biological study showed that compound 10 significantly impeded proliferation of the cell lines PC-3, LNCaP, and MatLyLu. The antimetastatic effects of compound 10 could be related with inhibition of MMP9 in the PC-3 and LNCaP human cell lines. On the basis of a study of the structure–activity relationship of these compounds, we propose that the presence of two methoxy groups at positions 6 and 7 of the indeno nucleus and a 4-hydroxy-3-methoxy phenyl substitution pattern at position 4 of the pyridine ring is decisive for these types of molecules to exert?very good antiproliferative and antimetastatic activities.
- Charris, Katiuska E.,Rodrigues, Juan R.,Ramírez, Hegira,Fernandez-Moreira, Esteban,ángel, Jorge E.,Charris, Jaime E.
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- Metal-free multicomponent synthesis of novel macrocyclic tetrathiadienes with cyano and amino groups
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The first synthesis of 5,12-diamino-7,14-bis(aryl)-1,4,8,11-tetrathiacyclotetradeca-5,12-diene-6,13-dicarbonitriles was performed as a multicomponent macroheterocyclization of malononitrile, aryl aldehydes, and 1,2-ethanedithiol in the presence of a catal
- Akhmadiev, Nail S.,Akhmetova, Vnira R.,Ibragimov, Askhat G.,Mescheryakova, Ekaterina S.
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p. 18768 - 18775
(2021/06/03)
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- A new type IV DES: a competent green catalyst and solvent for the synthesis of α,β-unsaturated diketones and dicyano compounds by Knoevenagel condensation reaction
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DESs are new and greener alternatives to ionic liquids formed by mixing components that are capable of forming hydrogen bonds between them. The strong hydrogen bond interactions between the constituents make a large depression in the melting points compared to pure constituents. They are emerging as green solvents and have loomed as adorable alternatives to conventional organic solvents and ionic liquids with unique properties. In the present article, four new CeCl3·7H2O-based DESs were developed and their physical properties were studied. Their activities were checked in the Knoevenagel condensation reaction of dimedone/malononitrile with various aldehydes. The recyclability of the catalyst/solvent was achieved up to five runs without much change in the activity.
- Shaibuna,Hiba,Theresa, Letcy V.,Sreekumar
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p. 14723 - 14732
(2020/09/21)
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- Enhanced catalytic activity of bio-fabricated ZnO NPs prepared by ultrasound-assisted route for the synthesis of tetraketone and benzylidenemalonitrile in hydrotropic aqueous medium
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Abstract: Mushroom-like mesoporous and hexagonal ZnO nanoparticles were synthesized from plant extract and chemical method respectively, by co-precipitation method in aqueous medium. Different morphological forms of ZnO NPs were characterized by XRD, TGA, FESEM, EDX, FTIR, UV–Vis and BET. Neem (Azadirachta indica) leaf extract and ultrasound irradiation have a crucial role in the formation of different morphologies of ZnO NPs. ZnO NPs synthesized from plant extract and hydrotrope show a synergistic effect that leads to efficient synthesis of benzylidenemalonitrile and tetraketone derivatives at room temperature in water. Simple preparation of the catalyst, excellent yields, reusability of catalyst with consistent activity and ease of product isolation are the most significant advantages of this green protocol. Graphic abstract: [Figure not available: see fulltext.]
- Attar, Suraj R.,Kamble, Santosh B.,Shinde, Bipin
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- Organocatalytic Cascade Knoevenagel–Michael Addition Reactions: Direct Synthesis of Polysubstituted 2-Amino-4H-Chromene Derivatives
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Abstract: In this report, we documented novel strategy for the synthesis of bioactive polysubstituted 2-amino-4H-chromine derivatives under a heterogeneous Al-MCM-41-LDH@APTES (ALAM) catalysis. A synthetic procedure is developed to prepare Al-MCM-41-LDH@APTES (ALAM) heterogeneous basic catalysts. Mesoporous Al-MCM-41 is functionalized by known grafting chemistry via layered double hydroxide (LDH) nanosheets and (3-aminopropyl)triethoxysilane (APTES) moiety as a basic organocatalyst. The resulting catalysts contain amino group functionality on the external surface as well as inside the layers and the basicity can be tuned by the loading of APTES. The samples were fully characterized by 29Si and 13C CP/MAS NMR, infrared absorption spectroscopy, TEM, XPS, EDX, TGA, XRD, CO2-TPD, N2 adsorption isotherms measurements, and they were successfully examined for the cascade type Knoevenagel–Michael addition reactions. The product yields associated with these substrates were optimized, and key reaction parameters affecting the yields were identified. The present catalytic method is simple and robust for diversity oriented synthesis which proceeds good to excellent yields without generating any hazards waste. The broad substrate scope, excellent functional group compatibility makes this protocol highly useful towards synthesis of polysubstituted α-cyanoacrylates, α-cyanoacrylonitriles and 2-amino-4H-chromenes with an electron-donating or electron-withdrawing group. We have also successfully established a flow reaction system, gram-scale synthesis as well as catalyst recyclability up to six catalytic cycles without appreciable loss of its activity. Graphic Abstract: [Figure not available: see fulltext.].
- Jadhav, Sanjay N.,Patil, Seema P.,Sahoo, Dipti Prava,Rath, Dharitri,Parida, Kulamani,Rode, Chandrashekhar V.
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p. 2331 - 2351
(2020/02/25)
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- An excellently stable heterovalent copper–organic framework based on Cu4I4 and Cu(COO)2N2 SBUs: The catalytic performance for CO2 cycloaddition reaction and Knoevenagel condensation reaction
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A novel 3D heterovalent Cu-based MOF, [Cu2Cu4I4(ANA)4(DMF)4]n (denoted as complex 1), was successfully designed and synthesized by the self-assembly of CuI and 5-aminonicotinic acid (HANA)
- Jin, Feng
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- Synthesis, crystal structure and catalytic property of a highly stable 3D Cu(II)-organic framework
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A three-dimensional (3D) Cu(II)-based MOF, [CuL·Cl]n (namely complex 1), was successfully generated through the in-situ reaction of CuCl2, NaN3, and 4-(4-cyanostyryl)pyridine. Notably, –CN and N3 ? ca
- Chen, Chunyan
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- Assembly of Two Self-Interpenetrating Metal-Organic Frameworks Based on a Trigonal Ligand: Syntheses, Crystal Structures, and Properties
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Two self-interpenetrating metal-organic frameworks (MOFs) 1 and 2 were designed and constructed through the coordination self-assembly of transition metal nodes and a trigonal ligand. They both exhibit interesting three-dimensional constructions with the
- Fan, Yuhang,Guo, Feng,Shi, Wenbing,Su, Changhua,Zhang, Xiuling
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- ADDITIVES FOR ELECTROLYTES IN LI-ION BATTERIES
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Method of improving the performance and safety of a Li-ion battery. The method comprises using a nitrile-based small organic compound of general formula I, V or IX outlined below in association with the electrolyte of the battery.
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Paragraph 0040; 0041
(2020/05/15)
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- Synthesis, biological evaluation, and molecular modeling of nitrile-containing compounds: Exploring multiple activities as anti-Alzheimer agents
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Based on the monoamine oxidase (MAO) inhibition properties of aminoheterocycles with a carbonitrile group we have carried out a systematic exploration to discover new classes of carbonitriles endowed with dual MAO and AChE inhibitory activities, and Aβ anti-aggregating properties. Eighty-three nitrile-containing compounds, 13 of which are new, were synthesized and evaluated. in vitro screening revealed that 31, a new compound, presented the best lead for trifunctional inhibition against MAO A (0.34 μM), MAO B (0.26 μM), and AChE (52 μM), while 32 exhibited a lead for selective MAO A (0.12 μM) inhibition coupled to AChE (48 μM) inhibition. Computational analysis revealed that the malononitrile group can find an advantageous position with the aromatic cleft and FAD of MAO A or MAO B. However, the total binding energy can be handicapped by an internal penalty caused by twisting of the ligand molecule and subsequent disruption of the conjugation (32 in MAO B compared to the conjugated 31). Conjugation is also important for AChE as well as the hydrophilic character of malononitrile that allows this group to be in close contact with the aqueous environment as seen for 83. Although the effect of 31 and 32 against Aβ1–42, was very weak, the effect of 63 and 65, and of the new compound 75, indicated that these compounds were able to disaggregate Aβ1–42 fibrils. The most effective was 63, a (phenylhydrazinylidene)propanedinitrile derivative that also inhibited MAO A (1.65 μM), making it a potential lead for Alzheimer's disease application.
- Silva, Daniel,Mendes, Eduarda,Summers, Eleanor J.,Neca, Ana,Jacinto, Ana C.,Reis, Telma,Agostinho, Paula,Bolea, Irene,Jimeno, M. Luisa,Mateus, M. Luisa,Oliveira-Campos, Ana M. F.,Unzeta, Mercedes,Marco-Contelles, José,Majekova, Magdalena,Ramsay, Rona R.,Carreiras, M. Carmo
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p. 215 - 231
(2019/09/03)
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- Synthesis, in vitro and in silico screening of 2-amino-4-aryl-6-(phenylthio) pyridine-3,5-dicarbonitriles as novel α-glucosidase inhibitors
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Inhibition of α-glucosidase enzyme is of prime importance for the treatment of diabetes mellitus (DM). Apart of many organic scaffolds, pyridine based compounds have previously been reported for wide range of bioactivities. The current study reports a series of pyridine based synthetic analogues for their α-glucosidase inhibitory potential assessed by in vitro, kinetics and in silico studies. For this purpose, 2-amino-4-aryl-6-(phenylthio)pyridine-3,5-dicarbonitriles 1–28 were synthesized and subjected to in vitro screening. Several analogs, including 1–3, 7, 9, 11–14, and 16 showed many folds increased inhibitory potential in comparison to the standard acarbose (IC50 = 750 ± 10 μM). Interestingly, compound 7 (IC50 = 55.6 ± 0.3 μM) exhibited thirteen-folds greater inhibition strength than the standard acarbose. Kinetic studies on most potent molecule 7 revealed a competitive type inhibitory mechanism. In silico studies have been performed to examine the binding mode of ligand (compound 7) with the active site residues of α-glucosidase enzyme.
- Ali, Muhammad,Faramarzi, Mohammad Ali,Jabbar, Abdul,Khan, Khalid Mohammed,Larijani, Bagher,Mahdavi, Mohammad,Perveen, Shahnaz,Salar, Uzma,Shamim, Shahbaz,Taha, Muhammad
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- Method used for preparing substituted 1, 3-malononitrile
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The invention belongs to the field of fine chemical product preparation and medicine intermediate synthesis, and relates to a method used for preparing substituted 1, 3-malononitrile. According to themethod, an aldehyde or a ketone and malononitrile are subjected to condensation reaction to prepare substituted 1, 3-malononitrile, wherein water is taken as a solvent, the aldehyde or the ketone andmalononitrile are subjected to Knoevenagel condensation under catalytic effect of zinc proline so as to obtain the corresponding substituted 1, 3-malononitrile. The method conditions are mild; operation is convenient; water is taken as a reaction solvent, so that the method is friendly to the environment; and the application prospect is promising.
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Paragraph 0022-0023
(2019/08/07)
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- Hypervalent Iodine(III)-Catalyzed Epoxidation of β-Cyanostyrenes
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A convenient approach for the synthesis of β-cyanoepoxides is illustrated by iodine(III)-catalyzed epoxidation of electron-deficient β-cyanostyrenes, wherein the active catalytic iodine(III) species was generated in situ. The epoxidation of β-cyanostyrenes was performed using 10 molpercent PhI as precatalyst in the presence of 2.0 equivalents Oxone as an oxidant and 2.4 equivalents of TFA as an additive at room temperature under ultrasonic radiations. The β-cyanoepoxides were isolated in good to excellent yields in a short reaction time.
- Mangaonkar, Saeesh R.,Singh, Fateh V.
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p. 4473 - 4486
(2019/11/21)
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- Cinnamonitrile adjuvants restore susceptibility to β-lactams against methicillin-resistant staphylococcus aureus
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β-Lactams are used routinely to treat Staphylococcus aureus infections. However, the emergence of methicillin-resistant S. aureus (MRSA) renders them clinically precarious. We describe a class of cinnamonitrile adjuvants that restore the activity of oxacillin (a penicillin member of the β-lactams) against MRSA. The lead adjuvants were tested against six important strains of MRSA, one vancomycin-intermediate S. aureus (VISA) strain, and one linezolid-resistant S. aureus strain. Five compounds out of 84 total compounds showed broad potentiation. At 8 μM (E)-3-(5-(3,4-dichlorobenzyl)-2-(trifluoromethoxy)phenyl)-2-(methylsulfonyl)acrylonitrile (26) potentiated oxacillin with a >4000-fold reduction of its MIC (from 256 to 0.06 mg·L-1). This class of adjuvants holds promise for reversal of the resistance phenotype of MRSA.
- Speri, Enrico,Kim, Choon,De Benedetti, Stefania,Qian, Yuanyuan,Lastochkin, Elena,Fishovitz, Jennifer,Fisher, Jed F.,Mobashery, Shahriar
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supporting information
p. 1148 - 1153
(2019/08/27)
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- Triazole-Pyridine Dicarbonitrile Targets Phosphodiesterase 4 to Induce Cytotoxicity in Lung Carcinoma Cells
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Phosphodiesterase 4 (PDE4) is a key enzyme involved in the hydrolysis of cyclic adenosine monophosphate (cAMP) and widely expressed in several types of cancers. The inhibition of PDE4 results in an increased concentration of intracellular cAMP levels that imparts the anti-inflammatory response in the target cells. In the present report, two series of triazolo-pyridine dicarbonitriles and substituted dihydropyridine dicarbonitriles were synthesized using green protocol (TBAB in refluxed water). We next evaluated the title compounds for their cytotoxicity towards lung cancer (A549) cells and identified 7′-[4-(methylsulfonyl)phenyl]-5′-oxo-1′,5′-dihydrospiro[cyclohexane-1,2′-[1,2,4]triazolo[1,5-a]pyridine]-6′,8′-dicarbonitrile (5h) and 7′-(1-methyl-1H-imidazol-2-yl)-5′-oxo-1′,5′-dihydrospiro[cyclohexane-1,2′-[1,2,4]triazolo[1,5-a]pyridine]-6′,8′-dicarbonitrile (5j) as lead analogs with the IC50 values of 15.2 and 24.1 μm, respectively. Furthermore, all the new compounds were tested for PDE4 inhibitory activity and 5j showed relatively good inhibitory activity towards PDE4 with inhibition of 50.9 % at 10 μm. In silico analysis demonstrated the favorable interaction of the title compounds with the target enzyme. Taken together, the present study introduces a new scaffold for the development of novel PDE4 inhibitors to fight against inflammatory diseases.
- Keerthy, Hosadurga K.,Mohan, Surender,Basappa,Bharathkumar, Hanumantharayappa,Rangappa, Shobith,Svensson, Fredrick,Bender, Andreas,Mohan, Chakrabhavi Dhananjaya,Rangappa, Kanchugarakoppal S.,Bhatnagar, Rakesh
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- An efficient Knoevenagel condensation of aldehydes with active methylene compounds over novel, robust CeZrO4?δ catalyst
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Abstract: In the present work, we explored novel CeZrO4?δ as a catalyst for Knoevenagel condensation of aldehydes with reactive methylene compounds like malononitrile and ethylcyanoacetate. For the present study, ceria, zirconia and CeZrO4
- Sahani, Amber J.,Burange, Anand S.,Jayaram, Radha V.
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p. 7805 - 7814
(2018/09/12)
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- Knoevenagel reaction catalyzed by a reusable Br?nsted acid based on 1-alkyl-1, 2, 4-triazolium tetrafluoroborate
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The Knoevenagel reaction is one of the most useful methods for the synthesis of α, β- unsaturated nitriles. We disclose an efficient protocol for the Knoevenagel reaction of aldehydes with malononitrile catalyzed by 1-alkyl-1, 2, 4-triazolium salts to aff
- Kandasamy, Elango,Nagarajan, Sankaranarayanan,Shaikh, Tanveer M.
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supporting information
p. 133 - 138
(2018/03/06)
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- Ultrasound-assisted rapid synthesis of β-cyanoepoxides using hypervalent iodine reagents
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An elegant approach for the rapid synthesis of β-cyanoepoxides 3 by the epoxidation of β-cyanostyrenes 1 with PIDA 2a is described. The epoxidation of β-cyanostyrenes 1 was performed with 1.2 equiv. of PIDA 2a in MeCN-H2O (1:1) at room temperature in ultrasonic bath. The epoxidation reactions were completed in short reaction time and β-cyanoepoxides 3 were isolated in 69–94% yields.
- Singh, Fateh V.,Mangaonkar, Saeesh R.,Kole, Priyanka B.
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supporting information
p. 2169 - 2176
(2018/07/21)
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- Dihydro-2: H -thiopyran-3(4 H)-one-1,1-dioxide-a versatile building block for the synthesis of new thiopyran-based heterocyclic systems
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Three series of new cyclic sulfones have been prepared by a one-pot multi-component reaction (MCR) starting from the readily available dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide. The in silico screening of the synthesized compounds revealed their high anti-inflammatory, antiarthritic, antiasthmatic and antiallergic potential coupled with the strong probability levels of cystinyl aminopeptidase inhibition. The key structures were confirmed by 2D NMR techniques.
- Palchykov, Vitalii A.,Chabanenko, Roman M.,Konshin, Valeriy V.,Dotsenko, Victor V.,Krivokolysko, Sergey G.,Chigorina, Elena A.,Horak, Yuriy I.,Lytvyn, Roman Z.,Vakhula, Andriy A.,Obushak, Mykola D.,Mazepa, Alexander V.
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p. 1403 - 1412
(2018/02/06)
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- An efficient protocol for the one-pot four-component synthesis of 6-amino-1,4-dihydropyrano[2,3-c]-pyrazole-5-carbonitrile derivatives using starch solution as a reaction media
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An efficient, high-yielding and rapid protocol has been developed for the synthesis of 6-amino-l,4-dihydropyrano [2,3-c]pyrazol-5-carbonitrile derivatives through four-component, one-pot cyclocondensation reaction of ethyl acetoacetate, hydrazine hydrate, aldehydes and malononitrile utilizing starch solution as a highly efficient homogenous catalyst. The use of a nontoxic, reusable and biodegradable catalyst is one of the superior advantagesof this protocol. Short reaction times, mild conditions, excellent product yields, simple work-up procedure and non use of toxic organic solvents are added advantages of this procedure.
- Vekariya, Rajesh H.,Patel, Kinjal D.,Patel, Hitesh D.
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p. 576 - 582
(2019/05/21)
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- Calcium ferrite, an efficient catalyst for knoevenagel condensation(A green approach)
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Calcium ferrite NPs catalyst have been used as a cheaper and highly efficient catalyst for Knoevenagel condensation of active methylene substrate with various carbonyl compounds affording condensed products in excellent yields in shorter reaction time. Th
- Pippal, Parveen,Singh, Prabal Pratap
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p. 1736 - 1743
(2017/10/27)
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- Β-Cyclodextrin as a Biomimetic Catalyst for the Efficient Synthesis of 4-Oxo-pyrido[1,2-a] Pyrimidine-3-Carbonitrile in Aqueous Medium
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Abstract: Supramolecular β-cyclodextrin as a highly efficient, biodegradable, and reusable catalyst for the synthesis of 4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbonitrile derivatives (4a–s) is investigated via a cascade reaction of aldehydes, malanonitrile
- Ghorad, Akash,Mahalle, Sagar,Khillare, Lalit D.,Sangshetti, Jaiprakash N.,Bhosle, Manisha R.
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p. 640 - 648
(2017/03/08)
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- “On-water” catalyst-free, one-pot synthesis of quaternary centered and spiro-tetrahydrothiophene-barbiturate hybrids
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A green and efficient method have been developed for the synthesis of quaternary centered and spiro-barbiturate-tetrahydrothiophene hybrids via Knoevenagel condensation,1,4-thia-Michael and intramolecular Aldol reactions using “on water” concept under catalyst-free conditions. Systematic studies were carried out to find the role of the water and total reaction concentration (0.086?M) to promote the reaction in two steps (one-pot). The use of water as a reaction medium, catalyst-free conditions, broad substrate scope, one-pot approach for the creation of quaternary centered and spiro molecules are the advantages of this method.
- Nagaraju, Sakkani,Sathish, Kota,Paplal, Banoth,Kashinath, Dhurke
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supporting information
p. 2865 - 2871
(2017/06/27)
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- Synthesis of novel 15-aryl-2,3,4,15-tetrahydrochromeno[2′,3′:4,5] pyrimido[6,1-b]quinazoline-1,9-diones
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A new series of 15-aryl-2,3,4,15-tetrahydrochromeno[2′,3′:4,5]pyrimido[6,1-b]quinazoline-1,9-diones was synthesised by the cyclisation of methyl anthranilate with ethyl N-(3-cyano-5-oxo-4-aryl-5,6,7,8-tetrahydro-4H-chromen-2-yl)formimidate derivatives, wh
- Kong, Xiu-Xiu,Cao, Yong-Nan,Xing, Zheng,Chen, Li-Zhuang,Han, Guang-Fan
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- Contemporary development in sequential Knoevenagel, Michael addition multicomponent reaction for the synthesis of 4-Aryl-5-oxo-5H-indeno[1,2-b]pyridine-3-carbonitrile
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An uncatalyzed efficient synthesis of bioactive pyridine derivatives has been investigated for the first time by a three-component sequential multicomponent reaction tackled with aromatic aldehydes, malononitrile, and 1,3-indandione via Knoevenagel condensation followed by Michael addition. The difference between the domino multicomponent and sequential multicomponent reaction is emphasized by this methodology. The reaction proceeds at ambient temperature without frequently useful N-source like ammonium salt for the construction of N-heterocycles, which makes this protocol a novel synthetic route for the preparation of the indenopyridine skeleton.
- Patravale, Ajinkya A.,Gore, Anil H.,Patil, Dipti R.,Kolekar, Govind B.,Deshmukh, Madhukar B.,Choudhari, Prafulla B.,Bhatia, Manish S.,Anbhule, Prashant V.
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p. 2919 - 2935
(2016/04/05)
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- Synthesis of novel ethyl 1-Aryl-3-methyl-8-oxo-1,8-dihydropyrano[2′,3′:4,5] pyrimido[6,1-b]quinazoline-2-carboxylate derivatives
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In this paper, a new series of ethyl 1-Aryl-3-methyl-8-oxo-1,8-dihydropyrano[2′,3′:4,5]pyrimido[6,1-b]quinazoline-2-carboxylate derivatives was synthesised by the cyclisation of methyl anthranilate with ethyl 5-cyano-6-[(ethoxymethylene)amino]-2-methyl-4-
- Shi, Qiu-Zhong,Cao, Yong-Nan,Ma, Shi-Bing,Wang, Guo-Xi,Han, Guang-Fan,Xing, Zheng
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p. 767 - 771
(2017/01/03)
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- Fluorous bispidine: A bifunctional reagent for copper-catalyzed oxidation and knoevenagel condensation reactions in water
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Fluorous bispidine-type ligands have been developed to facilitate its recovery and reusability and to demonstrate its bifunctional property as a ligand and base in copper-catalyzed aerobic oxidation, the Knoevenagel condensation and tandem oxidation/Knoevenagel condensation in water under mild conditions. Application of the fluorous ligand was also extended to the surfactant-free copper-catalyzed allylic and benzylic sp3 C-H oxidation reaction in water. The fluorous ligands could be recovered using F-SPE with recovery ranging from 91-97% and could be reused five times with little loss of activity.
- Ang, Wei Jie,Chng, Yong Sheng,Lam, Yulin
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p. 81415 - 81428
(2015/10/06)
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- Synthesis of two metal-porphyrin frameworks assembled from porphyrin building motifs, 5, 10, 15, 20-tetrapyridylporphyrin and their base catalyzed property
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Opening catalytically active sites in metal organic frameworks is an issue of fundamental importance for the development of effective and efficient catalysts. In this work, we first reported two metal metalloporphyrin-organic frameworks (MMPFs) with unocc
- Zhang, Weijie,Jiang, Pingping,Wang, Ying,Zhang, Jian,Zhang, Pingbo
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p. 100 - 104
(2015/09/28)
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- Synthesis of on resin poly(propylene imine) dendrimer and its use as organocatalyst
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Solid phase synthesis of poly(propylene imine) dendrimer is described. An iterative synthesis including double Michael addition of acrylonitrile to the primary amino groups on crosslinked polystyrene support followed by reduction of nitrile groups to amin
- Gopalakrishna Panicker, Rajesh Krishnan,Krishnapillai, Sreekumar
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supporting information
p. 2352 - 2354
(2014/05/06)
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- Bis-functionalization of 1,3-dienes through 1,4-conjugate addition of amphiphilic bis-π-allyl and related palladium intermediates
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Palladium-catalyzed three-component coupling of allylstannane, allyl chloride and a functionalized diene is described. Regioselective 1,4-functionalization of the Michael acceptor 1,3-diene is accomplished by the amphiphilic bis-π-allylpalladium complex.
- Baiju,Vijayan, Ajesh,Joseph, Nayana,Preethalayam, Preethanuj,Radhakrishnan,Suresh,Yamamoto, Yoshinori
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supporting information
p. 359 - 364
(2014/03/21)
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- Synthesis of novel 9,9-dimethyl-8,12-dihydro-9H-chromeno[3,2-e] [1,2,4] triazolo[1,5-c]pyrimidin-11(10H)-one derivatives
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Novel 9,9-dimethyl-8,12-dihydro-9H-chromeno[3,2-e][1,2,4]triazolo[1,5-c] pyrimidin-11(10H)-one derivatives were synthesised by the reactions of triethyl orthoformate or aromatic aldehydes with chromeno[2,3-d]pyrimidine derivatives, which were prepared by
- Wang, Zhong-Xia,Lia, Bei,Xing, Zheng,Chen, Li-Zhuang,Han, Guang-Fan
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p. 480 - 485
(2014/11/07)
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- Synthesis of Novel 4 H-Chromenes Containing a Pyrimidine-2-Thione Function in the Presence of Fe3O4 Magnetic Nanoparticles and Study of Their Antioxidant Activity
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The aim of the present work was to search for identification of novel reactive oxygen species (ROS) scavengers by testing new fused chromenopyrimidinethiones, which was synthesized using Fe3O4 nanoparticles. The new compounds were also tested for their cytotoxic activity. The obtained results showed that the incorporated pyrimidinethione moiety significantly increase antioxidant activity. In conclusion, the study of the pharmacological properties of the new chromenopyrimidinethiones allowed establishing new structure-activity relationships for splitting antioxidant and cytotoxic activity of these compounds.
- Khoobi, Mehdi,Ramazani, Ali,Hojjati, Zahra,Shakeri, Raheleh,Khoshneviszadeh, Mehdi,Ardestani, Susan Kaboudanian,Shafiee, Abbas,Foroumadi, Alireza,Joo, Sang Woo
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p. 1586 - 1595
(2015/10/29)
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- A highly efficient protocol for the regio- and stereo-selective synthesis of spiro pyrrolidine and pyrrolizidine derivatives by multicomponent reaction
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A series of novel spiro[acenaphthylene-1,2′-pyrrolidine] (4), spiro[acenaphthylene-1,2′-pyrrolizidine] (7), and spiro[indoline-3, 2′-pyrrolidine] derivatives (9) containing cyano group were successfully synthesized via a three-component 1,3-dipolar cycloaddition reaction of acenaphthenequinone or isatin, sarcosine or proline, and Knoevenagel adducts in refluxing aqueous methanol. In this intermolecular three-component combinatorial process it is amazing that three stereogenic centers with one spiro carbon are controlled very well. The structure and relative stereo-chemistry of cycloadducts were carried out by single crystal X-ray diffraction, as well as by the help of 1H, 13C, and HMBC spectroscopy.
- Dandia, Anshu,Jain, Anuj K.,Laxkar, Ashok K.,Bhati, Dharmendra S.
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p. 3180 - 3184
(2013/06/27)
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- Design, synthesis, docking study and biological evaluation of some novel tetrahydrochromeno [3′,4′:5,6]pyrano[2,3-b]quinolin-6(7H)-one derivatives against acetyl- and butyrylcholinesterase
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Novel hybrid derivatives of two known scaffolds; tetrahydroaminoquinoline and coumarin were synthesized and evaluated for both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) activities. By means of an efficient nanocatalyst, the reaction time for the syntheses of the target compounds was reduced. Subsequently, Ellman's modified method was used to evaluate the enzyme inhibitory activity of the synthesized structures. It was observed that most hybrid structures were moderate to potent inhibitors of AChE compared to Tacrine as the reference drug among which 7f with 4-fluorophenyl substituent was the most active compound (IC50 = 5 nM).
- Khoobi, Mehdi,Alipour, Masoumeh,Moradi, Alireza,Sakhteman, Amirhossein,Nadri, Hamid,Razavi, Seyyede Faeze,Ghandi, Mehdi,Foroumadi, Alireza,Shafiee, Abbas
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p. 291 - 300
(2013/10/01)
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- An environmentally friendlier approach - Ionic liquid catalysed, water promoted and grinding induced synthesis of highly functionalised pyrazole derivatives
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Grinding induced synthesis of highly functionalised pyrazoles derivatives by use of malanonitrile, phenyl hydrazine and diversified aldehyde. Ionic liquid is used as a catalyst with water, and no by-products form. A high yield is obtained and simple handl
- Singh, Jagdamba,Srivastava, Madhulika,Rai, Pratibha,Singh, Jaya
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p. 16994 - 16998
(2013/09/24)
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- Solvatochromism of catechol derivatives - Solute/solvent interactions
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The solvatochromism of nine push-pull substituted catechol derivatives has been studied in a set of 39 various solvents. The influence of successive methyl substitution at the catechol OH groups on the extent of the solvatochromic shift has been investiga
- Riedel, Franziska,Spange, Stefan
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p. 1261 - 1268
(2013/08/24)
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- An improved procedure for 2-amino-5-nitro-4,6-diarylcyclohex-1-ene-1,3,3- tricar bonitriles; carbonate on polymer support as mild and reusable catalyst
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A new catalytic system has been developed in the synthesis of 2-amino-5-nitro-4,6-diarylcyclohex-1-ene-1,3,3-tricarbonitriles using carbonate on polymer support (Amberlyst A-26 NaCO3 -). Short reaction time, simplicity of isolation, safe catalyst and high
- Prasanna,Raju, K. Mohana
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experimental part
p. 808 - 811
(2012/01/03)
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- Synthesis and enzyme inhibitory activities of highly functionalized pyridylmethyl-C-β-D-Glycosides
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Several pyridylmethyl-C-β-D-glycosides (3a-3l, 6a, and 6h) were synthesized by refluxing 3-(β-D-glucopyranosyl)/(β-D-cellobiosyl)- propanones and dicyanobenzylidenes with ammonium acetate in anhydrous toluene in moderate to good yields. The reaction invol
- Pandey, Vivek Parashar,Jaiswal, Natasha,Srivastava,Shukla, Sanjeev K.,Tripathi, Rama Pati
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body text
p. 132 - 146
(2012/02/01)
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- Chemoselective reaction of malononitrile with imine-ones and antifungal potential of products
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Condensation of malononitrile with 1-[4-(benzylideneamino.-phenyl]efhanones 1-10, the compounds containing both carbonnitrogen and carbon-oxygen double bonds, in equimolar ratio results in the formation of solid products, identified as-benzylidenemalononitrile and its derivatives 1a-10a on the basis of elemental analysis and spectral studies. The reaction of 1-10 with two moles of malononitrile also yields the same products 1a-10a by a chemoselective attack of malononitrile on carbonnitrogen double bond only rather than on both the reactive centres. The synthesized compounds 1a-10a have been evaluated for antifungal potential against Alternaria alternata, Colletotrichum capsici, Fusarium oxysporum, Myrothecium roridum and Ustilago tritici. Some of the compounds have been found to possess promising antifungal potential against the test fungi.
- Sidhu, Anjali,Sharma,Rai, Mangat
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experimental part
p. 247 - 250
(2010/11/04)
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- Mesoporous titanosilicate Ti-TUD-1 catalyzed Knoevenagel reaction: An efficient green synthesis of trisubstituted electrophilic olefins
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A new, efficient and green methodology has been developed for the Knoevenagel condensation using catalytic amount of mesoporous titanosilicate catalyst Ti-TUD-1, under mild conditions at room temperature. The method generates trisubstituted electrophilic olefins in high yields within short reaction time. The mesoporous nature of the catalyst having high surface area helps in binding the substrate to the active site. The advantage of this catalyst is its reusability with almost consistent reactivity thereby making it viable for industrial applications.
- Karmakar, Bikash,Chowdhury, Biswajit,Banerji, Julie
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experimental part
p. 601 - 605
(2010/11/18)
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- Diastereoselective synthesis of nicotine derivatives via 1,3-dipolar cycloaddition reactions
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(Chemical Equation Presented) A simple diastereoselective route to nicotine derivatives is presented. The one-pot three component 1,3-dipolar cycloaddition reaction of the Knoeevenagel adducts of a number of aromatic aldehydes and malononitrile with an azomethine ylide derived in situ from pyridine-3- carbaldehyde and sarcosine give access to nicotine derivatives in good yields.
- Ghandi, Mehdi,Taheri, Abuzar,Abbasi, Alireza
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body text
p. 611 - 615
(2010/09/05)
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