Recent Advances in Green Synthesis of 3,3′‐Spirooxindoles via Isatin–based One–pot Multicomponent Cascade Reactions in Aqueous Medium

Abstract

3,3′‐spirooxindoles are important synthetic target compounds and play special role in organic chemistry because of their extensive biological activities and applications of pharmaceutical lead discovery. In recent years, there has been a significant increase in design of new, atom economical and eco‐friendly isatin‐based one‐pot multicomponent cascade reactions in aqueous medium for the green synthesis of 3,3′‐spirooxindoles. In this review, the recent advances in this area were summarized and classified according to catalyst‐free, organic‐catalyzed, inorganic‐catalyzed, nanometer‐silica‐catalyzed and enzyme‐catalyzed reaction systems. These reviewed methods provide important inspiration for the synthesis of novel 3,3′‐spirooxindoles and design of new pharmaceutical compounds.

Zinc(II)‐poly(urea‐formaldehyde) supported on magnetic nanoparticles: A hybrid nanocatalyst for green synthesis of spiropyrans, spiroxanthenes, and spiropyrimidines

“…The use of green solvents or solvent‐free conditions instead of hazardous solvents in organic reactions, to avoid pollution from the environment, is enormously important in organic synthesis and water is an ideal choice. [ 35,36 ] Previous studies merely confirmed that the hydrogen bonds between water and substrates may accelerate many organic reactions. [ 37,38 ] Hence, herein we describe the green synthesis of spirooxindolopyrans, spirooxindoloxanthenes, and spirooxindolopyrimidines in the presence of a newly prepared organic–inorganic hybrid nanostructure (MNPs@SiO 2 @PUF@Zn) in aqueous conditions.…”

Cu (II)‐β‐cyclodextrin complex stabilized on magnetic nanoparticles: A retrievable hybrid promoter for green synthesis of spiropyrans

“…According to the principals of green chemistry, designing the green reaction conditions has become an important subject for the elimination of pollution from the environment in recent years. In this regard, the use of solvent‐free conditions or green solvents in organic reactions instead of hazardous solvents has been developed enormously in organic synthesis . Multi‐component reactions (MCRs) are powerful tools in organic synthesis because of short time, clean and high yield, and atom economy .…”

“…Multi‐component reactions (MCRs) are powerful tools in organic synthesis because of short time, clean and high yield, and atom economy . These advantages have encouraged scientists to use MCRs for synthesis of natural products including spiropyrans, which show a variety of biological activities, such as anti‐cancer, anti‐HIV, anti‐microbial, anti‐tubercular, anti‐viral and anti‐fungus . Some examples of 3,3‐spirooxindole cores with inhibited activity have been presented in Scheme .…”

Synthesis of Isoxazolopyridines and Spirooxindoles under Ultrasonic Irradiation and Evaluation of Their Antioxidant Activity

“…Consequently, several protocols for the synthesis of isoxazoles and spirooxindoles have been reported [19][20][21][22][23][24][25][26][27][28].…”