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Synthesis of Nanoparticles and Application of the Prepared Catalyst for Some Organic Reactions, Efficient Synthesis of New Thiophene Derivatives and Asymmetric Synthesis of Sulfonic Acid Derivatives

Saeidian, Hamdollah | 2009

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  1. Type of Document: Ph.D. Dissertation
  2. Language: Farsi
  3. Document No: 40005 (03)
  4. University: Sharif University of Technology
  5. Department: Chemistry
  6. Advisor(s): Matloubi Moghaddam, Firouz
  7. Abstract:
  8. ZnO nanopowder has been successfully synthesized by a microwave-assisted solution approach using Zn(CH3CO2)2.2H2O and NaOH. The results obtained from XRD, SEM and TEM show that the mean particle size is 30 nm. SEM and TEM micrographs of ZnO nanopowder also reveal that nanoparticles have spherical shape. A convenient one-pot multi-component reaction of aromatic aldehydes, enolizable ketones or β-keto esters and acetonitrile in the presence of acetyl chloride and 10 mol % ZnO nanoparticles for the synthesis of β-acetamido ketones/esters at room temperature is described. Catalytic activity of ZnO nanopowder for o-acylation of alcohol and phenol has also been investigated. On the other hand, the synthesis of pure α-Fe2O3 nanoparticles (30 nm) using a superabsorbent polymer (SAP) by the thermal decomposition is reported. The applicability of this nanostructure material was assessed by its catalytic effect on the Friedel-Crafts acylation. We have reported a new and efficient one-pot synthesis of thieno[2,3-b]indoles from various indoline-2- thiones and α-halocarbonyl compounds. The present procedure has advantage that, not only good functional group tolerance and high yields, but also the reaction can be preformed under mild conditions. In this part the synthesis of 2-Amino-3-aryl-5-substituted thiophenes as anti-inflammatory agents and fully substituted new indeno- and naphtho- fused thiophenes catalyzed by KF–Al2O3 under microwave irradiation are also reported. we have developed an efficient asymmetric synthesis of α,β-disubstituted γ-bisalkoxycarbonyl sulfonates via Michael addition of a lithiated sulfonate bearing 1,2:5,6-di-O-isopropylidene-α-D-allofuranose as a chiral auxiliary to Knoevenagel acceptors with one exception in good yields (62-79%) and excellent diastereoselectivities (ds = 69-96%). The cleavage of the chiral sugar auxiliary demonstrated in typical case proceeded without any epimerization or racemization to form the corresponding isopropyl sulfonate in good overall yield (48%) and excellent diastereomeric and enantiomeric excess (de, ee ≥ 98%).

  9. Keywords:
  10. Zinc Oxide ; Hematite ; Thioamides ; Nanoparticles ; Sulfonic Acid ; Ferrugineol ; Allofuranose

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