Catalytic Stereoselective Synthesis of Diverse Oxindoles and Spirooxindoles from Isatins

Abstract

A strategy for the efficient two-step synthesis of triazole derivatives of oxindoles and spirooxindoles is presented. Using a common set of N-propargylated isatins, a series of mechanistically-distinct stereoselective reactions with different combinations of nucleophiles and catalysts provide access to diverse hydroxy-oxindoles, spiroindolones, and spirocyclic oxazoline structures. The resulting N-propargylated oxindoles are then converted to triazoles using copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions. Overall, this strategy affords a 64-member pilot-scale library of diverse oxindoles and spirooxindoles.

Eco‐friendly Polyethylene Glycol‐400 as a Rapid and Efficient Recyclable Reaction Medium for the Synthesis of Anticancer Isatin‐linked Chalcones and Their 3‐Hydroxy Precursor

“…All compounds, 3f – j , were synthesized in a similar manner with slight variation in reaction time as reported in Table . Physical and spectral data of compounds, 3a – e , were comparable with earlier reported compounds in our published paper .…”

Synthesis, characterization and thermal decomposition of 2’-amino-6’-(1H-indol-3-yl)-1-methyl-2-oxospiro-[indoline-3,4’-pyran]-3’,5’-dicarbonitrile under non-isothermal condition in nitrogen atmosphere

“…The heterocyclic spirooxindoles are attractive targets of medicinal chemistry due to the wide range of pharmacological activities such as anticancer, anti-microbial, anti-malarial,anti-mycobacterium, anti-oxidant and anti-fungal activities [3]. Catalytic stereo-selective synthesis of diverse oxindoles and spirooxindoles were obtained from isatins [4]. Their preparative methods suffer from tedious synthetic routes, longer reaction time, drastic reaction conditions, as well as narrow substrate scope [5].…”

Catalyst‐Free One‐Pot Tandem Reduction of Oxo and Ene/Yne Functionalities by Hydrazine: Synthesis of Substituted Oxindoles from Isatins

“…[1] Substituted and unsubstituted oxindoles also serve as crucial synthetic precursors for the synthesis of highly desirable indole-based heterocycles and alkaloids. [1] Substituted and unsubstituted oxindoles also serve as crucial synthetic precursors for the synthesis of highly desirable indole-based heterocycles and alkaloids.…”