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

• Published in: Synthetic communications Vol. 53; no. 14; pp. 1153 - 1163
• Main Authors: Matloubi Moghaddam, F., Kavoosi, Leila, Aghamiri, Bagher
• Format: Journal Article
• Language: English
• Published: PHILADELPHIA Taylor & Francis 18.07.2023; Taylor & Francis Ltd
• Subjects: 2-imino-5-(1-alkyl-2-oxoindolin-3-ylidene) thiazolidin-4-one; Cascade chemical reactions; Chemical reactions; Chemical synthesis; Chemistry; Chemistry, Organic; Condensates; Eco-friendly; Ethanol; medicinal scaffolds; Physical Sciences; Science & Technology; Substitutes; 2-imino-5-(1-alkyl-2-oxoindolin-3-ylidene) thiazolidin-4-one; ANTICANCER; Eco-friendly; CONDENSATION; INHIBITORS; medicinal scaffolds; HYBRIDS
• ISSN: 0039-7911; 1532-2432
• DOI: 10.1080/00397911.2023.2213360

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.