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Phytochemical and 2DNMR Investigation of Iranian Endemic Plants and Synthesis of Fused Polycyclic Heterocycles

Taheri, Salman | 2010

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  1. Type of Document: Ph.D. Dissertation
  2. Language: Farsi
  3. Document No: 40627 (03)
  4. University: Sharif University of Technology
  5. Department: Chemistry
  6. Advisor(s): Matloubi Moghaddam, Firouz; Tafazzoli, Mohsen; Amin, Gholamreza
  7. Abstract:
  8. Members of Centaurea species are common traditional medicines throughout the world. For this reason medicinal plants are the targets of intense Phytochemical studies. In this research we have investigated Centautea Golestanica which are members of this genus and endemic of Iran. In this research, One Flavonoid, two Sesquiterpenelactones and two triterpenoides were elucidated by advanced spectroscopic techniques such as IR, MS, 1H NMR, 13C NMR and 2D NMR. In continuation of this research, we have reported new and efficient methods for the synthesis of hitherto unknown indole-annulated pentacyclic indolylhydroisoquino lines and naphthooxazocines via tandem dinucleophilic addition of indolin-2-thiones and 2-naphtholes to N-alkylisoquinolinium and N- alkylquinolinum salts. This new approach provides a powerful entry into polycyclic structures containing nitrogen and sulfur related to alkaloids. We also prepared three important class of fused polycyclic indole heterocycles, thiopyrano [2, 3-b] indoles and Thiopyranocoumarin via Hetero Diels-Alder reaction of thioindoles with various aldehydes and thieno [2, 3-b] indoles via Condensation of Isocyanide and Indolin-2-thiones.

  9. Keywords:
  10. Fused Heterocycle ; Indoline-2-Thion ; Diels Alder Reaction ; Centaurea Golestanica ; Thieno (2,3-b)Indole ; Indolyltetrahydroisoquinoline ; Naphthooxazocine ; Thiopyranocoumarine

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