Approaches towards 3‐Substituted‐3‐hydroxyoxindole and Spirooxindole‐Pyran Derivatives in a Reaction of Isatin with Acetylacetone in Aqueous Media. Issue 43 (26th November 2019)

• Record Type: Journal Article
• Authors: Chandran, R.; Prabhakaran, S. M.; Kumar, Vaneet; Thakar, Snehal Rajendra; Tiwari, Keshri Nath
• Is Part Of: ChemistrySelect. Volume 4:Issue 43(2019)
• Page Start: 12757
• Page End: 12761
• Publication Date: 2019-11-26
• Subjects: acetylacetone -- DABCO -- 3-hydroxyoxindole -- spirooxindole-pyran -- water; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201903301
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: The synthetic utility of C1 and C3 nucleophilic behavior of acetylacetone in a reaction with isatin for two distinct pharmaceutically relevant scaffolds 3‐substituted 3‐hydroxyoxindole and spirooxindole‐pyran in water is presented. The protocol offers environmentally benign conditions, wide substrate scope, and good to the very good chemical yield of products. The developed methodology has the potential to generate a library of useful synthetic compounds that are of pharmaceutical interest. A plausible mechanism for the formation of products based on the outcome of the reaction is also rationalized. Abstract : 3‐substituted 3‐hydroxyoxindole and spirooxindole‐pyran derivatives were synthesized by utilizing C1 and C3 nucleophilic behavior of acetylacetone with isatin in water. The developed methodology has the potential to generate a library of useful synthetic compounds that are of pharmaceutical interest. Mild reaction conditions, broad functional group tolerance and operationally simple workup procedures are advantages of protocol. A plausible mechanism for the formation of products based on the outcome of reaction was also rationalized.