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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  

    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... 

    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.
     

    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... 

    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  

    One-pot synthesis of dispiro[oxindole-3,3′-pyrrolidines] by three-component [3+2] cycloadditions of in situ-generated azomethine ylides with 3-benzylidene-2,3-dihydro-1H-indol-2-ones

    , Article Helvetica Chimica Acta ; Volume 96, Issue 11 , 2013 , Pages 2103-2114 ; 0018019X (ISSN) Matloubia Moghaddam, F ; Kiamehr, M ; Reza Khodabakhshi, M ; Jebeli Javan, M ; Fathi, S ; Villinger, A ; Iaroshenko, V. O ; Langer, P ; Sharif University of Technology
    2013
    Abstract
    An efficient one-pot, three-component synthesis of novel dispiro[oxindole-3,3′-pyrrolidines] by 1,3-dipolar cycloaddition of azomethine ylides, in situ generated by reaction of 1,2-diones with sarcosine and subsequent decarboxylation, with a series of (E)-3-benzylidene-2,3-dihydro- 1H-indol-2-ones is reported. Molecular complexity is generated in only one synthetic step. All reactions proceed with excellent regioselectivity and in good-to-excellent yields. The workup is easy, the reaction times are short, and no catalyst is required. © 2013 Verlag Helvetica Chimica Acta AG, Zürich