The Molecular Diversity Scope of Oxindole Derivatives in Organic Synthesis

Abstract

: The role of oxindole derivatives is discussed as starting materials in diverse organic reactions including two and more components between the years 2014 until 2020. Oxindoles are famous because of their biological properties for instance chromanone-fused polycyclic pyrrolidinyl-dispirooxindoles, functionalized polycyclic spiro-fused carbocyclicoxindole, and 3,3-disubstituted oxindoles have anti-cancer, anti-tumor, and anti-microbial properties, respectively. Therefore, various methods for synthesizing the oxindole structures have received more attention in organic chemistry.

Palladium-catalyzed Heck/aminocarbonylation of alkene-tethered carbamoyl chlorides with nitro compounds for the synthesis of carbamoyl-substituted oxindoles

“…4 In addition, oxindoles can also be widely used as useful intermediates in various organic reactions. 5 Therefore, a series of synthetic methods have been developed for the construction of oxindoles, and some of the most popular methods are based on transition-metal-catalyzed cascade cyclizations. 6 Considering their privileged bioactivities and broad applications, exploring more synthetic methods to access oxindoles is of great interest and has drawn much attention from organic chemists.…”

Synthesis of unsymmetrical diaryl oxindoles/isoquinolinediones using 2-phenoxy-1H-benzo[d]imidazole as an integrated diarylating reagent

“…Moreover, 3,3-disubstituted 2-oxindoles have also been used as key building blocks for the synthesis of indole-related fine chemicals. 2 Due to their importance, a number of reliable methods for their preparation have been developed, which mainly include alkylation/arylation of oxindoles, Michael addition reactions of oxindoles with enones, Mannich type reactions of isatin imines, arylation of cyclic amides, radical cyclization and oxidative coupling reactions of pre-functionalized acyclic substrates, etc. 3,4 Meanwhile, it was also noted that many of the known methods are only suitable for the preparation of symmetrical 3,3-disubstituted 2-oxindoles.…”

Electrochemical Fe-catalysed radical cyclization for the synthesis of oxindoles

“…1,2 In addition, they are also versatile targets in synthetic chemistry and frequently exploited as intermediates in the synthesis of structurally diverse natural products. [3][4][5][6][7] As such, the development of novel strategies to access oxindoles remains of high significance in the synthetic community. In particular, methods for sustainable and efficient preparation of carbonyl-containing oxindoles are extremely attractive as these core structures are found in a wide variety of natural products and can be used as key intermediates in total synthesis of indole alkaloids (Scheme 1A).…”