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

Abstract

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.

Graphical Abstract

Keywords:

• Eco-friendly
• medicinal scaffolds
• 2-imino-5-(1-alkyl-2-oxoindolin-3-ylidene) thiazolidin-4-one

Acknowledgments

The authors would like to thank the Sharif University of Technology Research Council for partial financial support. The authors are also so grateful to Dr. Alireza Fattahi from the Sharif University of Technology for his help in computational analysis.