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    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  

    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... 

    , 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.
     

    1, 3- Dipolar Cycloaddition Reactions of Azomethine Ylides of Ninhydrin with Chalcones and Investigation of Asymmetric Addition of TMSCN to Imines

    , M.Sc. Thesis Sharif University of Technology Assempour, Nazanin (Author) ; Saidi, Mohammad Reza (Supervisor) ; Jadidi, Khosrow (Supervisor) ; Mehrdad, Morteza (Co-Advisor)
    Abstract
    Part 1
    1,3-dipolar cycloaddition reactions offer convenient routes for the construction of a variety of five-membered heterocycles. This thesis represents a simple synthetic method via 1,3-dipolar cycloaddition reaction to prepare a novel class of spiro pyrrolidines and spiro pyrrolizidines which exhibit many biological activities. Non-stabilized azomethine ylides which generated in situ by the decarboxylative condensation of ninhydrin with proline and sarcosine were used as a 1,3-dipoles. On the other hand, chalcone and its derivatives with an impressive array of pharmacological activities were the dipolarophiles in these reactions. The reactions were carried out through reflax... 

    , 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... 

    Synthesis of Polycyclic Heterocycles using Benzofuranone Scaffolds via 1,3-Dipolar Cycloaddition Reactions under Green Chemistry Conditions

    , Ph.D. Dissertation Sharif University of Technology Hosseinzadeh, Nouraddin (Author) ; Matloubi Moghaddam, Firouz (Supervisor) ; Foroumadi, Alireza (Co-Supervisor)
    Abstract
    Spirooxindole compounds are naturally occurring compounds and have significant biological activities due to their unique spatial structure. Spirooxindole compounds, especially spiro oxindoles containing acyclic ring at C-3 position of oxindole, have high interaction capability with large productions. Therefore, these compounds are important in medicinal chemistry. The method used for the synthesis of spirooxindole compounds has been introduced. In general, for the synthesis of these compounds, isatin derivatives are used in 1 and 3 dipolar reactions in the presence of various solvents and catalysts. Due to the presence of quaternary spiro carbon with sp3 hybridization in the structure of... 

    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  

    Copper nanoparticles supported on CeO2 as an efficient catalyst for click reactions of azides with alkynes

    , Article Catalysis Communications ; Volume 85 , 2016 , Pages 13-16 ; 15667367 (ISSN) Amini, M ; Hassandoost, R ; Bagherzadeh, M ; Gautam, S ; Chae, K. H ; Sharif University of Technology
    Elsevier  2016
    Abstract
    Readily prepared copper nanoparticles supported on CeO2 have been found to effectively catalyse the 1,3-dipolar cycloaddition (CuAAC) of a variety terminal alkynes and organic azides generated in situ from sodium azide and different organic halides furnishing the corresponding 1,2,3-triazoles in excellent yields. Cu nanoparticles supported on CeO2 have been characterized by X-ray diffraction analysis, energy dispersive X-ray analysis, scanning electron microscope and transmission electron microscope. The salient features of the present protocol are shorter reaction time, mild reaction conditions, reusability of the catalyst, and applicability to a wide range of substrates. © 2016 Elsevier... 

    Regio- and diastereoselective synthesis of novel polycyclic pyrrolo[2,1- a]isoquinolines bearing indeno[1,2- b]quinoxaline moieties by a three-component [3+2]-cycloaddition reaction

    , Article Synlett ; Volume 31, Issue 3 , 2020 , Pages 267-271 Matloubi Moghaddam, F ; Moafi, A ; Jafari, B ; Vilinger, A ; Langer, P ; Sharif University of Technology
    Georg Thieme Verlag  2020
    Abstract
    A regio- and diastereoselective synthesis of 2,3-dihydro-10b′ H -spiro[indeno[1,2- b ]quinoxaline-11,1′-pyrrolo[2,1- a ]isoquinoline]-2′,3′-diylbis(phenylmethanone) derivatives containing four contiguous chiral stereocenters was achieved through 1,3-dipolar cycloaddition of isoquinolinium N -ylides in a one-pot three-component reaction. The desired products were obtained in short reaction times and in moderate to high yields (up to 92%) under relatively mild reaction conditions. The structure and relative stereochemistry of the desired product was confirmed by X-ray diffraction analysis. © 2020 Georg Thieme Verlag. All rights reserved