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  3. سنتز مکان گزین، دیاستریومرگزین و فضا گزین ترکیبات آلی جدید حاوی اسکلت های ایمینو تیازولیدین، تیازولیدینون، کینوکسالین و اکسیندول
سنتز مکان گزین، دیاستریومرگزین و فضا گزین ترکیبات آلی جدید حاوی اسکلت های ایمینو تیازولیدین، تیازولیدینون، کینوکسالین و اکسیندول
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سنتز مکان گزین، دیاستریومرگزین و فضا گزین ترکیبات آلی جدید حاوی اسکلت های ایمینو تیازولیدین، تیازولیدینون، کینوکسالین و اکسیندول

کاوسی قافی، لیلا Kavoosi Ghafi, Leila

Regio-, Diastereo-, and Stereo-Selective Synthesis of Novel Organic Compounds Containing Imino-Thiazolidine, Thiazolidinone, Quinoxaline, and Oxindole Scaffolds

Kavoosi Ghafi, Leila | 2025

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  1. Type of Document: Ph.D. Dissertation
  2. Language: Farsi
  3. Document No: 58697 (03)
  4. University: Sharif University of Technology
  5. Department: Chemistry
  6. Advisor(s): Matloubi Moghaddam, Firouz
  7. Abstract:
  8. Eco-friendly and efficient methods for synthesis new organic derivatives with potential pharmaceutical and scientific applications have been introduced. Initially, a regioselective coupling reaction between 2-imino-thiazolidin-4-one (pseudothiohydantoin) and oxindole derivatives has been reported, leading to the synthesis of 2-imino-5-(1-alkyl-2-oxoindolin-3-ylidene)thiazolidin-4-one derivatives. This method achieves excellent yields and high purity simply by washing with water and ethanol. it is recognized as the first straightforward protocol for the rapid condensation of pseudothiohydantoin with isatin derivatives. Moreover, the formation of the Z-isomer of the products, i.e., regioselectivity, has been confirmed through computational studies. In another part of the study, a regioselective, diastereoselective, and kinetically controlled reaction for the synthesis of thioxothiazolidin-indolin-2-ones, oxoindoline-carbamodithioate hybrids, and their transformation into dispirocyclopentane-bisoxindoles under base catalysis has been reported. In this reaction, only the kinetic products of thioxothiazolidin-indolin-2-ones were obtained, which were subsequently converted into dispirocyclopentane-bisoxindoles. Significant advantages of this approach include excellent regioselectivity and diastereoselectivity, ease of reaction processing, and a one-step synthetic procedure, which aligns with the principles of green chemistry. Additionally, methods for the synthesis of indeno-quinoxaline-thiazolidin-2-thione hybrids and bis-indeno-quinoxaline-dicarbamodithioates via the reaction of carbon disulfide, various amines, and 2-(11H-indeno[1,2-b]quinoxalin-11-ylidene)-1-phenyl-ethan-1-one derivatives have been reported. This approach provides excellent regio- and diastereoselectivity, high yield, mild reaction conditions, straightforward processing, and a one-step synthetic protocol, all in accordance with the principles of green chemistry. Furthermore, the scalability of this method has been validated for successful gram-scale synthesis. This process is ideal for future pharmaceutical screening, as it minimizes resource consumption and waste production, aligning with the principles of green chemistry. Moreover, bis-indeno-quinoxaline-dicarbamodithioate and indeno-quinoxaline-thiazolidin-2-thione derivatives exhibit photoluminescence (fluorescence) properties. Fluorescent organic compounds have extensive applications, particularly in sensing and bioimaging, prompting an investigation into their potential applications in these fields. Overall, this study highlights efficient and cost-effective synthetic methods in line with green chemistry, demonstrating the possible applications of these compounds in various scientific, pharmaceutical, and industrial fields.
  9. Keywords:
  10. Oxindole ; Thiazolidindione ; Iminothiazolidine ; Quinoxaline ; Diastereoselective ; Stereoselective Synthesis

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