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Synthesis and Characterization of some Heterocyclic Compounds Containing Nitrogen Using Oxindole Intermediate Skeleton

Moafi, Atiyeh | 2019

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  1. Type of Document: Ph.D. Dissertation
  2. Language: Farsi
  3. Document No: 52432 (03)
  4. University: Sharif University of Technology
  5. Department: Chemistry
  6. Advisor(s): Matloubi Moghadam, Firouz
  7. Abstract:
  8. In the first part of this thesis provided an efficient and easy method for the synthesis of 3-alkylidin-2-oxindoles containing tetrahydropyrazine structure in the absence of catalysts under green conditions. The oxindole unit represents an important structural motif found in natural products and biologically relevant compounds. On the other hand, pyrazines are important and well-known compounds found in nature and many medicinal compounds. According to the aforementioned, it seems that the oxindole compounds containing the pyrazine rings exhibit high biological activity.In the second chapter of this thesis, an efficient study to synthesize thiopyrano [2,3-b] quinoline containing indole structure is done. Indole is a very important heterocyclic compound that is abundant in nature and is found in a wide range of biologically significant natural compounds. On the other hand, thiopyrano [2,3-b] quinolines are tricyclic ring systems containing a thiopyran moiety condensed with a quinoline nucleus, and are currently found to be associated with some interesting bioactivities. Therefore, the presence of these two structures in one compound seems to increase its biological activity.In the next section, regio and diastereoselective synthesis of pyrrole [2,1-a] isoquinoline containing the quinoxaline skeleton is provided. The importance of this project is not only due to the presence of important pyrrolo [2,1-a] isoquinoline and quinoxaline rings in the product structure, but also for the synthesis of only one diastereomer out of the four contiguous chiral stereocenters bearing the products.In the last section of this thesis, a novel three component synthesize of spiro benzimidazolidine bearing indole scaffold is done. Spiro compounds are very important structures that are found in many natural and pharmaceutical compounds. On the other hand, benzimidazoles are the fused heterocyclic ring systems which form an integral part of vitamin B12. They often play crucial role in numerous diseases via various mechanisms, therefore these products have potential applications in medicinal chemistry and in organic synthesis
  9. Keywords:
  10. Heterocylic Compounds ; Oxindole ; Pyrazin ; Indole Synthesis ; Diastromer Selectivity ; Nitrogen Containing Heterocyclic Rings ; Spiropyran ; Multicomponent Reaction ; Benzimidazol

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