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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

Eslami, Mohammad | 2019

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  1. Type of Document: Ph.D. Dissertation
  2. Language: Farsi
  3. Document No: 51915 (03)
  4. University: Sharif University of Technology
  5. Department: Chemistry
  6. Advisor(s): Matloubi Moghaddam, Firouz; Balalai, Saeed
  7. Abstract:
  8. 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 on spirocycles of interest is required. On the other hand, spirocycles have been considered difficult to synthesize due to the presence of a quaternary carbon. In this regard and given our ongoing interest in the synthesis of spirooxindole compounds, we envisioned a direct pathway to access spirooxindole six-membered heterocycles. It is noteworthy that, the synthetic protocols avoids traditional chromatography and recrystallization purifications by washing away crude products with cold diethyl ether so that the pure product can be obtained shortly and easily after the experiment. The X-ray, HRMS, 1HNMR, 13CNMR, and FT-IR analysis data confirmed the structure of a typical products.In the next section, heterogenous catalysts based on magnetic nanoparticles were synthesized. In these catalysts, magnetic nanoparticles were coated with defferent fuctional groups to produce a catalyst with magnetic properties which is easily separated from the reaction medium. The structure of synthesized catalyst was characterized using techniques such as transmission electron microscopy (TEM), scanning electron microscope (SEM), Fourier transform infrared spectroscopy (FTIR), and CHNS elemental analysis. Easy preparation, low cost, biodegradability and high thermal stability are advantages of these catalysts. At the end, catalytic properties of resulted catalyst were investigated in many types of organic reaction such as Click reaction, ullmann coupling, multicomponent reaction and reduction of nitro arenes
  9. Keywords:
  10. Isatin ; Spirooxindole ; Spirodihydropyrane ; Spiropyridazine ; Magnetic Nanodot ; Click Chemistry ; Green Chemistry ; Arylamine ; Diaryl Ether

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