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    Cu2O nanocrystals with various morphology: Synthesis, characterization and catalytic properties

    , Article Chinese Chemical Letters ; 2017 ; 10018417 (ISSN) Bagherzadeh, M ; Mousavi, N. A ; Amini, M ; Gautam, S ; Singh, J. P ; Chae, K. H ; Sharif University of Technology
    Elsevier B.V  2017
    Abstract
    Cu2O nanocubes, octahedra, spheres and truncated rhombic dodecahedral were prepared and their structural, morphological, and electronic properties were investigated by X-ray diffraction analysis, X-ray absorption near edge structure, scanning electron microscope and transmission electron microscope and X-ray absorption near edge structure. Cu2O nanocrystals were successfully employed to catalyze the 1,3-dipolar cycloaddition reaction for the synthesis of 1,4-disubstituted triazoles. Cu2O nanocubes and octahedral showed the superior catalytic performance in the cycloaddition reaction. These results reveal that crystal-plane engineering of oxide catalysts is a useful strategy for developing... 

    Cu2O nanocrystals with various morphology: synthesis, characterization and catalytic properties

    , Article Chinese Chemical Letters ; Volume 28, Issue 5 , 2017 , Pages 1125-1130 ; 10018417 (ISSN) Bagherzadeh, M ; Mousavi, N. A ; Amini, M ; Gautam, S ; Singh, J. P ; Chae, K. H ; Sharif University of Technology
    Elsevier B.V  2017
    Abstract
    Cu2O nanocubes, octahedra, spheres and truncated rhombic dodecahedral were prepared and their structural, morphological, and electronic properties were investigated by X-ray diffraction analysis, X-ray absorption near edge structure, scanning electron microscope and transmission electron microscope and X-ray absorption near edge structure. Cu2O nanocrystals were successfully employed to catalyze the 1,3-dipolar cycloaddition reaction for the synthesis of 1,4-disubstituted triazoles. Cu2O nanocubes and octahedral showed the superior catalytic performance in the cycloaddition reaction. These results reveal that crystal-plane engineering of oxide catalysts is a useful strategy for developing... 

    Site-selective and regioselective Diels-Alder reaction of allenyl aryl ethers

    , Article Monatshefte fur Chemie ; Volume 141, Issue 12 , 2010 , Pages 1333-1337 ; 00269247 (ISSN) Matloubi Moghaddam, F ; Kiamehr, M ; Sharif University of Technology
    2010
    Abstract
    The site-selectivity and regioselectivity of Diels-Alder reactions of allenyl aryl ethers with cyclopentadiene and acrolein were studied. While cyclopentadiene (as an electron-rich diene) only reacted with the external double bond of allenyl aryl ethers to provide the site-selective normal electron demand Diels-Alder cycloadducts, acrolein (as an electron-deficient diene) reacted with the C1-C2 π bond of allenyl aryl ethers to provide the site- and regioselective hetero-Diels-Alder cycloadducts as exclusive products  

    Two new copper(II) complexes with chelating N,O-type bidentate ligands: synthesis, characterization, crystal structure and catalytic activity in azide–alkyne cycloaddition reaction

    , Article Inorganica Chimica Acta ; Volume 466 , 2017 , Pages 398-404 ; 00201693 (ISSN) Bagherzadeh, M ; Bayrami, A ; Kia, R ; Amini, M ; Kershaw Cook, L. J ; Raithby, P. R ; Sharif University of Technology
    Abstract
    Tetra-coordinated copper(II) complexes, [CuL2] and [Cu(phox)2], were synthesized by reaction of 1-((4-bromophenylimino)methyl)naphthalen-2-ol, HL, and 2-(2′-hydroxyphenyl)-2-oxazoline, Hphox, ligands with copper acetate, respectively. The complexes were characterized using FT-IR spectroscopy, elemental analyses, and their solid state structures were confirmed by single crystal X-ray diffraction. The catalytic activity of the complexes was evaluated in one-pot azide–alkyne cycloaddition (AAC) click reaction in water without need of any additional agent. The [CuL2] complex showed high catalytic activity in this reaction‌‌‌ and 1,2,3-triazole derivatives were produced in moderate to good... 

    Ultrasound-assisted, ZnBr2-catalyzed regio-and stereoselective synthesis of novel 3,3′-dispiropyrrolidine bisoxindole derivatives via 1,3-dipolar cycloaddition reaction of an azomethine ylide

    , Article Arkivoc ; Volume 2017, Issue 5 , 2017 , Pages 20-31 ; 15517004 (ISSN) Kiamehr, M ; Khodabakhshi, M. R ; Moghaddam, F. M ; Villinger, A ; Langer, P ; Sharif University of Technology
    Arkat  2017
    Abstract
    Ultrasound irradiation in presence of 20% ZnBr2 effectively promotes regio-and stereo-selective cycloaddition reaction of azomethine ylide with a series of (E)-3-benzylideneindolin-2-ones to afford 3,3′-dispiropyrrolidine bisoxindole derivatives in excellent yields in methanol at room temperature. The factors affecting the cycloaddition reaction, for example solvent, catalyst, ultrasonic irradiation, are examined in detail to find the mildest conditions and highest reaction yields. The structure and stereochemistry of cycloadducts were determined by spectroscopic data and confirmed by X-ray crystallographic analysis. © ARKAT USA, Inc  

    Ab initio study of solvent effects on rate of 1,3-dipolar cycloadditions of benzonitrile oxide and various dipolarophiles

    , Article Journal of Chemical Research - Part S ; Issue 2 , 2003 , Pages 91-95 ; 03082342 (ISSN) Rajaeian, E ; Monajjemi, M ; Gholami, M. R ; Sharif University of Technology
    2003
    Abstract
    Ab initio molecular orbital calculations have been used to investigate the structures and the transition states of 1,3-dipolar cycloadditions between benzonitrile oxide with ethylene, cyclopentene, acrylonitrile and tetracyanoethylene in heptane and water: calculations reveal enhanced hydrogen bonding of a water molecule to the transition states for the cycloaddition 1,3-dipolar of reaction of benzonitrile oxide with cyclopentene, the optimal interaction energies being 0.7 kcal/mol more favourable for hydrogen bonding to the oxygen atom in the transition states than for the reactants  

    Gas-phase diels-alder cycloaddition reaction in the presence of methanol and water vapor

    , Article Journal of Physical Organic Chemistry ; Volume 16, Issue 1 , 2003 , Pages 79-83 ; 08943230 (ISSN) Gholami, M. R ; Talebi, B. A ; Sharif University of Technology
    2003
    Abstract
    Hydrogen bonding effects of protic solvents, apart from bulk properties, on the reaction rate of the cycloaddition of cylopentadiene and vinyl acetate in the presence of water and methanol in the gas phase were investigated. The results showed that methanol increases the reaction rate in the gas phase more than the water. This is attributed to the stronger hydrogen bonding effect of methanol in this phase. Ab initio and semi-empirical calculations show that methanol stabilizes the transition state of the reaction more than water. This arises from two different origins, distribution of charge and geometry of the hydrogen bond. Copyright © 2002 John Wiley & Sons, Ltd  

    Multiparameter correlation of the rate of a [2 + 2] cycloaddition reaction versus solvophobicity parameter and normalized polarity parameter in aqueous solutions

    , Article Journal of Physical Organic Chemistry ; Volume 13, Issue 8 , 2000 , Pages 468-472 ; 08943230 (ISSN) Gholami, M. R ; Habibi Yangjeh, A ; Sharif University of Technology
    John Wiley and Sons Ltd  2000
    Abstract
    The second-order rate constants of the [2 + 2] cycloaddition reaction between diethyl azodicarboxylate and ethyl vinyl ether were obtained spectrophotometrically in various solvents and aqueous solutions of 1,4-dioxane and methanol at 30 ± 0.1 °C. In all media except aqueous solutions, a very good linear correlation of logk2 vs ETN (normalized polarity parameter) was obtained (n = 11, r = 0.991, s = 0.086). Because of the higher polarity of the activated complex relative to the reactants, the rate of the reaction increase with increasing solvent polarity parameter. Dual-parameter correlation of logk2 vs π* (dipolarity/polarizability) and a (hydrogen bonding acidity) also gives good results... 

    , M.Sc. Thesis Sharif University of Technology Khodabakhshi, Mohammad Reza (Author) ; Matloubi Moghaddam, Firouz (Supervisor)
    Abstract
    1,3-Dipolar cycloaddition reactions constitute one of the most fundamental reactions for construction of five-membered heterocyclic compounds Spiro and dispirooxindoles have become important synthetic targets as these structural frameworks form the core units of many naturally occurring molecules that possess abundant biological activities .In this report we used (E)-Aryl ideneindolinones as unusual dipolarophiles for synthesis of dispirooxindoles. In follow different bifunctional nucleophiles for example 1,3-dicarbonyl, phenol, thioindole can be used in synthesis of benzoxazocines We have reported a new and efficient synthesis of benzoxazocines via unique tandem 1,3-dinucleophilic addition... 

    Highly efficient synthesis of pyrimido[4,5-d]pyrimidine-2,4-dione derivatives catalyzed by iodine

    , Article Tetrahedron Letters ; 2014 , p. 4720-4723 Moghaddam, F. M ; Khodabakhshi, M. R ; Aminaee, M ; Sharif University of Technology
    Abstract
    A new and efficient synthesis of pyrimido[4,5-d]pyrimidine-2,4-dione derivatives through the reaction of 6-aminouracils and N,N′-bis(arylmethylidene) arylmethane in the presence of molecular iodine as a readily available and feasible catalyst  

    A one-pot, three-component regiospecific synthesis of dispiropyrrolidines containing a thiophenone ring via 1,3-dipolar cycloaddition reactions of azomethine ylides

    , Article Tetrahedron Letters ; Volume 54, Issue 20 , May , 2013 , Pages 2520-2524 ; 00404039 (ISSN) Moghaddam, F. M ; Khodabakhshi, M. R ; Ghahremannejad, Z ; Foroushani, B. K ; Ng, S. W ; Sharif University of Technology
    2013
    Abstract
    The synthesis of new dispiropyrrolidines containing a thiophenone ring has been achieved by a one-pot, three-component 1,3-dipolar cycloaddition reaction. Unsaturated thiophenone dipolarophiles were reacted with azomethine ylides, generated in situ from sarcosine and cycloketone derivatives (isatin, ninhydrin, acenaphthoquinone), to produce the corresponding cycloadducts in good yields (70-90%). The cycloaddition reaction was found to be highly regio- and diastereoselective  

    SBA-15-supported Cu (II)/Schiff-base complex as an efficient and recyclable catalyst for one-pot azide-alkyne cycloaddition reaction

    , Article Journal of Porous Materials ; Volume 26, Issue 5 , 2019 , Pages 1427-1433 ; 13802224 (ISSN) Banan, A ; Nikbakht, F ; Ataie, S ; Sharif University of Technology
    Springer New York LLC  2019
    Abstract
    A new complex of copper (II) was synthesized through the reaction of a Schiff-base, 4-(((2-hydroxyethyl)imino)methyl)phenol, with CuCl2·2H2O and, then, immobilization on SBA-15 support. Both immobilized and free copper complexes were characterized using different techniques such as FT-IR, elemental analysis (CHN), SEM, XRD and TEM, and were utilized as catalysts in one-pot azide-alkyne cycloaddition (AAC) reaction. Both catalysts showed high activity in conversion of various substrates to corresponding triazole compounds. The reaction was performed in water under mild condition and without any extra additives. The prepared catalyst was recovered and reused in 5 runs without any significant... 

    Kinetics study of a Diels-Alder reaction in mixtures of an ionic liquid with molecular solvents

    , Article Journal of Physical Organic Chemistry ; Volume 21, Issue 9 , 2008 , Pages 783-788 ; 08943230 (ISSN) Harifi Mood, A. R ; Habibi Yangjeh, A ; Gholami, M. R ; Sharif University of Technology
    2008
    Abstract
    The second-order rate constants for cycloaddition reaction of cyclopentadiene with naphthoquinone were determined spectrophotometrically in various compositions of 1-(1-butyl)-3-methylimidazolium terafluoroborate ([bmim]BF4) with water and methanol at 25°C. Rate constants of the reaction in pure solvents are in the order of water > [bmim]BF 4 > methanol. Rate constants of the reaction decrease sharply with mole fraction of the ionic liquid in aqueous solutions and increase slightly to a maximum in alcoholic mixtures. Multi-parameter correlation of logk 2 versus solute-solvent interaction parameters demonstrated that solvophobicity parameter (Sp), hydrogen-bond donor acidity (α) and... 

    Study of Catalytic Activity of Zirconium-Based Metal-Organic Frameworks in the Epoxide Ring-Opening Reactions

    , M.Sc. Thesis Sharif University of Technology Chegeni, Mohsen (Author) ; Bagherzadeh, Mojtaba (Supervisor)
    Abstract
    In current research, two zirconium-based metal-organic frameworks, MIP-202 (Zr) and UIO-66(CO2H)2 were employed as catalysts in the epoxy ring-opening reactions by amino and alcoholic nucleophiles. Firstly, these metal-organic frameworks were prepared under mild synthetic conditions and then characterized by means of spectral techniques such as X-ray diffraction (XRD), nuclear magnetic resonance spectroscopy (NMR), Fourier transform infrared spectroscopy (FT-IR), electron microscopy Scanning (SEM) and X-ray energy diffraction (EDAX) spectroscopy were confirmed. Finally, their catalytic activity in epoxy ring-opening reactions was investigated and in to determine optimal conditions, the... 

    Synthesis of 1,4-disubstituted 1,2,3-triazoles from aromatic α-bromoketones, sodium azide and terminal acetylenes via Cu/Cu(OTf)2-catalyzed click reaction under microwave irradiation

    , Article Zeitschrift fur Naturforschung - Section C Journal of Biosciences ; Volume 68, Issue 4 , Apr , 2013 , Pages 391-396 ; 09395075 (ISSN) Fazeli, A ; Oskooie, H. A ; Beheshtiha, Y. S ; Heravi, M. M ; Matloubi Moghaddam, F ; Koushki Foroushani, B ; Sharif University of Technology
    2013
    Abstract
    Reaction of aromatic α-bromoketones, sodium azide and aromatic or aliphatic terminal acetylenes in the presence of Cu/Cu(OTf)2following the classical method (aqueous acetonitrile at room temperature) and under microwave irradiation (H2O at 85 °C) leads to 1,4-disubstituted 1,2,3-triazoles as the final products after simple filtration  

    Synthesis of Thiopyrano Indole Annulated Benzo -δ-Sultones Via Domino Knoevenagele Hetero-Dielse Alder Reaction& Synthesis of Dispiro Compounds Via On-Pot Three Componet 1,3- Dipolar Cycloaddition

    , M.Sc. Thesis Sharif University of Technology Qahremannjad, Zahra (Author) ; Moghaddam, Matloubi (Supervisor)
    Abstract
    The domino-Knoevenagele hetero-Dielse Alder reaction is an efficient synthesis of complex compounds like natural products from simple substrates and highly diverse molecules. In the first chapter, synthesis of pyran, pyranopyran, pyrano-thiopyran heterocycles and [6,5] pyranopyrrole derivatives are achieved via domino Knoevenagele hetero-Dielse Alder reaction of O-acrylated and o- propargylated salicylaldehyde derivatives with thiooxindole and 4- hydroxyl dithiocoumarin. We discovered a new and efficient synthesis of a great variety of thiopyrano indole annulated benzo -δ-sultones via domino Knoevenagele hetero-Dielse Alder reaction of thiooxindole derivatives and (E)-2-formylphenyl... 

    Synthesis of Spiro Heterocyclic Compounds by Using Isatin Based 1,3-Dipolar

    , M.Sc. Thesis Sharif University of Technology Aghamiri, Bagher (Author) ; Matloubi Moghaddam, Firouz (Supervisor)
    Abstract
    Today, heterocycle compounds have become increasingly important in organic chemistry syntheses. Many extracellular compounds have a confirmed biological property. Due to the high bioactivity of these compounds, the development of their synthetic methods has received considerable attention and numerous reports have been published on their synthesis. One of the most commonly used examples is terazosin. It was first marketed as a blood pressure lowering drug but was later used in the treatment of benign prostate gland.Another important class of these compounds may be the different derivatives of the pyrimidine molecule used in the treatment of cancer. The use of hetero- cyclic compounds is not... 

    Synthesis and Characterization of Cu(II) Complexes with an Bidentate N,O-type Schiff Base Ligands and Study of the Catalytic Properties in Click Reactions

    , M.Sc. Thesis Sharif University of Technology Bayrami, Arshad (Author) ; Bagherzadeh, Mojtaba (Supervisor)
    Abstract
    Two new copper(II) complexes, [CuL2] and [Cu(phox)2], were synthesized by reaction of 1-((4-bromophenylimino)methyl)naphthalen-2-ol, HL, and 2-(2′-hydroxyphenyl)-2-oxazoline, Hphox, as ligands and copper(II) acetate mono-hydrate with the ratio 2:1 (ligand:metal), respectively. For characterization and structure determination of synthesized complexes, different techniques were performed such as FT-IR, elemental analyses (CHN), and X-ray crystallography. The geometry around Cu atom is almost square planar in both complexes. The catalytic activity of the complexes was evaluated in azide–alkyne cycloaddition reaction in water without need of any additional agent. The reaction conditions for the... 

    Use of Suitable Methods in Synthesis of Spiropyrrolididne Oxindole, Polysubstituted Thiophene, Thiopyrano Benzosultone and Pyrimidines by Cycloaddition Reactions

    , Ph.D. Dissertation Sharif University of Technology Khodabakhshi, Mohammad Reza (Author) ; Matloubi Moghaddam, Firouz (Supervisor)
    Abstract
    We have reported a new and efficient synthesis of a broad spectrum of heterotetracyclic thiopyranoindole via knovenagel hetero diels alder reaction.Fused pyrimidines have attracted considerable attention in synthetic organic chemistry because of their wide range of biological activities pharmaceutical and therapeutic properties, and antibacterial, antiviral, antitumor, and anti-inflammatory activities. We have reported a new efficient method for synthesis of pyrimidines fused to coumarine, uracile, cyclohexane and triamino pyrimidine structures. The major benefits of the current study are high yields, short reaction times, mild reaction conditions and available materials..We have also... 

    , M.Sc. Thesis Sharif University of Technology Fathi, Shaghayegh (Author) ; Mtlobi Moghadam, Firouz (Supervisor)
    Abstract
    The one pot, three component 1,3-dipolar cycloaddition reaction of azomethine ylides with a series of new dipolarophiles (E)-3 -benzylidene- indolin-2 -ones in methanol under the reflux condition yields ,3′-dispiropyrrolidine oxindole library. The product is produced with high regioselectivity. Catalyst free, excellent yield , easy workup process, short reaction time, and convenient operation are the characteristics of this procedure. NMR and X-ray are used to determine the structure and stereochemistry of cycloadduct products.