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Synthesis of Pd-based Magnetic Nanocatalyst and its Application on C-F Activation in Coupling Reactions, Using Sm for Cyanation Reacion and Diastereoselective Synthesis of Novel Hit Compounds and Their Pharmacological Evaluation

Karimi, Ashkan | 2017

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  1. Type of Document: M.Sc. Thesis
  2. Language: Farsi
  3. Document No: 49811 (03)
  4. University: Sharif University of Technology
  5. Department: Chemistry
  6. Advisor(s): Matloubi Moghaddam, Firouz
  7. Abstract:
  8. Formation of C-C and C-hetero atom bonds in coupling reactions is among the most important organic chemistry reactions, which is useful for achieving the complex molecules from simple ones. The goal of this thesis, was using the organometallic and also metal free methods in coupling reactions and getting the advantage of them in the synthesis of novel hit compounds. In this way, some novel reactions were designed and some novel catalysts were synthesised and identified. Finally, computational quantum chemistry and computational drug design were used as powerful tools for supporting the reaction mechanism, electronic and structural studies and pharmacological evaluation. C-X bond activation in aryl halides is a class of coupling reactions. In the first chapter of this thesis, Palladium was immobilised on a nanomagnetic supported 2-amino pyridine ligand. This novel catalyst with the average size of 15nm was identified and used in amination, Suzuki and homocoupling reaction of aryl halides and C-F bond was activated effectively in a very mild condition. In the second section, the double Michael addition of dibenzyl ketone on thio-oxindoles and oxindoles, which result in the diastereoselective synthesis of spiro compounds, was studied. The selectivity of this reactions was studied by Gaussian computations and the solvent effect was checked out. Their pharmacological activities of the products were evaluated by docking and QSAR methods. In the other part, a report describes the first use of samarium powder in the cyanataion reaction of aryl halides in a ligand-free, aqueous media and very mild condition. Another kinds of coupling reactions belong to C-H activation of aryl halides. In these cases, there is an ortho directing group usually. In the fourth chapter, the first mechanistic study on para C-H activation was described by Density Functional Theory (DFT). Also, all the transition states and intermediates were identified. The pharmacological activities of para olefination of the tertiary anilines products were evaluated by QSAR and docking. One of the C-C bond formation reactions is intramolecular cyclopropanation. In the last section of this thesis, the reaction of amides and thioamides containing olefin group in a novel position, with a complex of titanium and Grignard reagent was studied. From this selective reaction, in some cases, novel bicyclic compounds with high diastereoselectivity were obtained and in the other cases, reduction alkylation occurred. The high selectivity of these reactions was studied by quantum computations. In this projects, a novel multi-component reaction and a novel elimination reaction was introduced. Also, the pharmacological activities of the reaction products were evaluated by QSAR method
  9. Keywords:
  10. Docking ; Coupling Reactions ; Cyclopentadiene ; Reductive N-Alkylation ; Spirooxindole ; Quantitative Structure-Activity Relationship (QSAR)Model ; Double Micheal Reaction ; Nanomagnetic Catalyst ; C-F Bond Activation

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