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    Synthesis of Spiro Polycyclic Heterocycles Using Isatin and Designing Iron Oxide-based Heterogeneous Nano Catalyst for Organic Transformations under Green Chemistry Conditions

    , Ph.D. Dissertation Sharif University of Technology Eslami, Mohammad (Author) ; Matloubi Moghaddam, Firouz (Supervisor) ; Balalai, Saeed (Co-Supervisor)
    Abstract
    Spirocycles have been employed both as core structures and appended to the periphery of molecules in drug discovery. The major advantage that spirocycles offer as core structures is their inherent three-dimensional nature and concomitant ability to project functionality in all three dimensions. Spirocycles have been employed both as core structures and appended to the periphery of molecules in drug discovery. The major advantage that spiro cyclesoffer as core structures is their inherent three-dimensional nature and concomitant ability to project functionality in all three dimensions. However, to take full advantage of spirocycles, the ability to control stereochemistry at multiple positions... 

    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  

    Diastereoselective construction of a functionalized dihydro-pyridazine-based spirooxindole scaffold: Via C-3 umpolung of isatin N, N ′-cyclic azomethine imine

    , Article New Journal of Chemistry ; Volume 43, Issue 26 , 2019 , Pages 10318-10323 ; 11440546 (ISSN) Matloubi Moghaddam, F ; Eslami, M ; Siahpoosh, A ; Hoda, G ; Sharif University of Technology
    Royal Society of Chemistry  2019
    Abstract
    Herein, functionalized spiro[indoline-3,5′-pyrazolo[1,2-a]pyridazine]-7′-carbonitrile containing two contiguous chiral stereocenters was efficiently synthesized in a satisfactory yield (up to 91% yield) and with excellent diastereoselectivity. We have reached this satisfactory yield by DABCO-catalyzed [3+3] annulation reactions of an isatin N,N′-cyclic azomethine imine 1,3-dipole with a Knoevenagel intermediate in dichloromethane (DCM) as solvent at ambient temperature; this was an entirely new strategy for creating one quaternary stereogenic center at the position-3 of an oxindole structure using an abnormal tandem Michael addition, N-cyclization, and a unique approach via the azomethine... 

    Diastereoselective construction of a functionalized dihydro-pyridazine-based spirooxindole scaffold: via C-3 umpolung of isatin N, N ′-cyclic azomethine imine

    , Article New Journal of Chemistry ; Volume 43, Issue 26 , 2019 , Pages 10318-10323 ; 11440546 (ISSN) Matloubi Moghaddam, F ; Eslami, M ; Siahpoosh, A ; Hoda, G ; Sharif University of Technology
    Royal Society of Chemistry  2019
    Abstract
    Herein, functionalized spiro[indoline-3,5′-pyrazolo[1,2-a]pyridazine]-7′-carbonitrile containing two contiguous chiral stereocenters was efficiently synthesized in a satisfactory yield (up to 91% yield) and with excellent diastereoselectivity. We have reached this satisfactory yield by DABCO-catalyzed [3+3] annulation reactions of an isatin N,N′-cyclic azomethine imine 1,3-dipole with a Knoevenagel intermediate in dichloromethane (DCM) as solvent at ambient temperature; this was an entirely new strategy for creating one quaternary stereogenic center at the position-3 of an oxindole structure using an abnormal tandem Michael addition, N-cyclization, and a unique approach via the azomethine...