Recent advances in organocatalytic methods for the synthesis of disubstituted 2- and 3-indolinones

Abstract

In recent years, organocatalysis has enhanced its importance as a tool for the synthesis of enantiomerically enriched compounds. Among the candidates for organocatalysis, the construction of asymmetric quaternary carbons is regarded as a challenging problem in organic synthesis. In particular, 3,3'-disubstituted oxindoles have one or more asymmetric quaternary carbon atoms and they represent a large family of bioactive compounds and synthetic derivatives that mimicry natural products. Therefore they are good targets for drug candidates and in the last two years many papers have appeared on organocatalytic methods for the synthesis of 3,3'-disubstituted oxindoles. Moreover, in the last few years 2-substituted and 2,2'-disubtituted 3-indolinones have also attracted the interest of chemists. This review aims to cover the literature on these topics from its origin to the end of 2011.

Molecular diversity of spirooxindoles. Synthesis and biological activity

“…However, only the Michael addition leads to the formation of spirolinked 2 -thiopyrrolidonyl fragments. Thus 3,3 -and 3,2 -thiopyrrolidonyl spirooxindoles can be formed depending on the structure of the 2-oxindolic core [120,121] (Scheme 58).…”

Palladium(0)-Catalyzed Benzylic C(<i>sp</i>³)–H Functionalization for the Concise Synthesis of Heterocycles and Its Applications

“…Spirooxindole natural products, which are characterized by the fused spiro-structure of their oxindole core bearing various rings at its C3 position, have attracted considerable attention from numerous synthetic chemistry groups because of their complex structures and their pronounced biological activities [44][45][46][47][48][49][50][51][52][53] (Fig. 1).…”

Theoretical Studies of Colvent Effect for Oxindole Derivatives Using Polarizable Continuum Model

“…Oxindole frameworks are found in many bioactive compounds and natural products. Due to this synthetic methods and transformations of oxindole skeletons have been extensively investigated [2][3][4][5] . The naturally occurring oxindole derivative convolutamydine has been found to exhibit potent activity in the differentiation of HL-60 human plomyelocyticleukemic cells.…”