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Synthesis of Polycyclic Heterocycles using Benzofuranone Scaffolds via 1,3-Dipolar Cycloaddition Reactions under Green Chemistry Conditions

Hosseinzadeh, Nouraddin | 2023

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  1. Type of Document: Ph.D. Dissertation
  2. Language: Farsi
  3. Document No: 55803 (03)
  4. University: Sharif University of Technology
  5. Department: Chemistry
  6. Advisor(s): Matloubi Moghaddam, Firouz; Foroumadi, Alireza
  7. Abstract:
  8. Spirooxindole compounds are naturally occurring compounds and have significant biological activities due to their unique spatial structure. Spirooxindole compounds, especially spiro oxindoles containing acyclic ring at C-3 position of oxindole, have high interaction capability with large productions. Therefore, these compounds are important in medicinal chemistry. The method used for the synthesis of spirooxindole compounds has been introduced. In general, for the synthesis of these compounds, isatin derivatives are used in 1 and 3 dipolar reactions in the presence of various solvents and catalysts. Due to the presence of quaternary spiro carbon with sp3 hybridization in the structure of spirooxindole compounds, the reported methods have one or less disadvantages: complex reaction conditions, use of toxic and dangerous solvents, use of reflux conditions, high reaction time and low efficiency. It is possible to introduce simple and easy methods for the synthesis of these very important compounds. Considering the spiro compounds and the interest of our research group to investigate the methods of synthesis of this group of compounds, in this treatise, the synthesis of spirooxindole is made through a new environmentally friendly process using benzofuranone, isatin and sarcosine derivatives in the presence of phosphoric ionic liquid under are affected. They were synthesized under ultrasonic and microwave conditions. In these new processes, spiroscindol compounds were synthesized in the environment in a short reaction time with high efficiency. The methods used were simple and easy. All compounds were isolated in analytical form and, the synthesized products were obtained by simple filtration and elution with diethyl ether without the need for additional purification steps including column chromatography and recrystallization. X-ray, NMR, FT-IR analyzes were used to determine the final products
  9. Keywords:
  10. Isatin ; Spirooxindole ; 1,3-Dipolar-Cycloaddition Reaction ; Green Chemistry ; Ionic Liquids ; Ultrasonic Waves ; Microwave Radiation ; Benzofuranone

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