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Facile one-pot, domino reaction to synthesize (Z)-2-imino-5-(1-alkyl-2-oxoindolin-3-ylidene)thiazolidin-4-one derivatives and its DFT study for the E/Z confirmation structure

Matloubi Moghaddam, F ; Sharif University of Technology | 2023

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  1. Type of Document: Article
  2. DOI: 10.1080/00397911.2023.2213360
  3. Publisher: Taylor and Francis Ltd , 2023
  4. Abstract:
  5. In this publication, we reported an eco-friendly procedure for the efficient synthesis of 2-imino-5-(1-alkyl-2-oxoindolin-3-ylidene) thiazolidin-4-one derivatives with a stereospecific coupling reaction between 2-imino-thiazolidin-4-one (pseudothiohydantoin) and cyano-substituted oxindole derivatives. Thus, a variety of new thiazolidin-oxindole derivatives with potential medicinal applications have been synthesized with an effective and economical method, focusing on sustainable chemistry. The final products have been obtained in excellent yields together with high purity after washing with water and ethanol. This publication is the first easy protocol to be reported for the rapid condensation of pseudothiohydantoin with substituted isatins. In addition, the stereospecificity, which led to the formation of the Z- isomer of the products is validated using computational calculations. © 2023 Taylor & Francis Group, LLC
  6. Keywords:
  7. 2-imino-5-(1-alkyl-2-oxoindolin-3-ylidene) thiazolidin-4-one ; Eco-friendly ; Medicinal scaffolds
  8. Source: Synthetic Communications ; Volume 53, Issue 14 , 2023 , Pages 1153-1163 ; 00397911 (ISSN)
  9. URL: https://www.tandfonline.com/doi/full/10.1080/00397911.2023.2213360