Approaches towards 3‐Substituted‐3‐hydroxyoxindole and Spirooxindole‐Pyran Derivatives in a Reaction of Isatin with Acetylacetone in Aqueous Media

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.

Copper-Catalyzed Thiolation of Terminal Alkynes Employing Thiocyanate as the Sulfur Source Leading to Enaminone-Based Alkynyl Sulfides under Ambient Conditions

“…Thiocyanated enaminones, preferably, offer tremendous synthetic potential, and hence, functionalization of the C­(sp 2 )–H bond of enaminone to the C­(sp 2 )–S bond has been successfully developed . We became interested in exploring the synthetic ability of underutilized thiocyanated enaminones based on our experience with enaminone-based multicomponent reactions . Herein, we report the α-thiocyanation of enaminones and consequential copper-catalyzed C­(sp)–S bond formation of thiocyanate with terminal alkynes under ambient conditions (Figure E).…”