75833-70-4

Upstream product

• 120-72-9 indole 
• 91-56-5 indole-2,3-dione 

Downstream Products

• 13637-37-1 1H,1'H-[3,3']biindolyl 

Relevant academic research and scientific papers

Indium Catalyzed Sequential Regioselective Remote C?H Indolylation and Rearrangement Reaction of Peroxyoxindole

Indium-catalyzed sequential remote C?H functionalization (C-6 position) and C3-indolylation of peroxyoxindole using indole is described for the synthesis of terindolinone derivatives. Whereas, N-substituted 3-phenyl peroxyoxindole derivatives undergoes consecutive skeletal rearrangement to generate transient carbocation, which has been trapped with indole nucleophile to generate 2-(1H-indol-3-yl)-4-alkyl-benzo[b][1,4]oxazin-3(4H)-one derivatives. In contrast with Indium (III) Chloride, FeCl3 ? 6H2O facilitates oxidative cleavage of the peroxyoxindole (Hock cleavage) and further reaction with indole to afford biologically important trisindoline derivatives. A plausible mechanism has been proposed for these reactions with experimental evidences. (Figure presented.).

Lambert Salt-Initiated Development of Friedel–Crafts Reaction on Isatin to Access Distinct Derivatives of Oxindoles

Herein, a mild metal-free and efficacious route for the synthesis of biologically important 3-aryl oxindole derivatives is described. Using Lambert salt-initiated hydroarylation of isatin, a diverse array of monoarylated products, symmetrical/unsymmetrical double-arylated products, and deoxygenated hydroarylated products could be synthesized from the single starting substrate in good to excellent yields. A preliminary mechanistic study revealed that the reaction proceeds via a monoarylated product followed by a nucleophilic attack by another electron-rich arene nucleophile under mild conditions. The potential of newly synthesized symmetric/unsymmetric 3,3-disubstituted oxindole, 3-substituted 3-hydroxy oxindoles, 3,3-di(indolyl)indolin-2-ones, and α-aryl oxindoles as valuable building blocks is further illustrated.

3-Hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-one as a versatile intermediate for retro-Henry and Friedel-Crafts alkylation reactions in aqueous medium

The first example of a retro-Henry type reaction is reported using 3-hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-ones which are prepared via catalyst-free Henry reaction of 3,5-dimethyl-4-nitroisoxazole and isatin. These compounds were used

2D-2D Nanocomposite of MoS2-Graphitic Carbon Nitride as Multifunctional Catalyst for Sustainable Synthesis of C3-Functionalized Indoles

A nanocomposite of two-dimensional MoS2 supported on graphitic C3N4 nanosheets has been prepared by a facile ultrasonication method followed by demonstrating its ability to catalyze the synthesis of several indole derivatives. The as-prepared nanocomposite catalyst was characterized in detail by using different microscopic and spectroscopic techniques to understand its structure and physicochemical properties. Subsequently, this nanocomposite catalyst was used as a heterogeneous multifunctional catalyst to synthesize several C3-functionalized indoles in the aqueous medium. The employed strategy also provided very good catalyst recyclability and versatility for the synthesis of various precursors of medicinally significant indoles, such as serotonin, melatonin, and various β-carboline alkaloids. In addition, a natural product derivate has been prepared on the gram-scale by using this methodology. Furthermore, high atom economy (100 %) and lower E-factor (0.042) makes this strategy a sustainable approach for the synthesis of C3-functionalized indoles.

An efficient Friedel-Crafts alkylation for the synthesis of 3-indolyl-3-hydroxy oxindoles and unsymmetrical 3,3-diaryl oxindoles catalyzed by Dabco-based ionic liquids in water

A convenient and rapid method for the syntheses of 3-indolyl-3-hydroxy oxindoles and unsymmetrical 3,3-diaryl oxindoles has been developed by using Dabco-based ionic liquid catalysts. The two ionic liquid catalysts, [Dabco-H][BF4] and [Dabco-H][HSO4] were found to be highly efficient catalysts for controlled 3-indolylation of isatins in water. When [Dabco-H][BF4] was employed as the catalyst in water at 55 °C, the reaction between isatins and indoles stops at the step of addition of the two components and afforded 3-indolyl-3-hydroxy oxindoles. While increasing the reaction temperature to 90 °C, the catalyst [Dabco-H][HSO4] could drive the reaction further and afford symmetrical 3,3-diindolyl oxindoles. By using the two kinds of ionic liquids, a two-step protocol for the efficient synthesis of unsymmetrical 3,3-diaryl oxindoles has also been developed. The use of water as the reaction medium makes the process environmentally benign. The catalysts can be recycled five times without activity loss.

Synthesis of symmetrical and unsymmetrical 3,3-di(indolyl)indolin-2-ones under controlled catalysis of ionic liquids

Three ionic liquids, [BMIM][BF4] doped with 60 mol % of LiCl ([BMIM][BF4]-LiCl), N,N,N,N-tetramethylguanidinium trifluoroacetate (TMGT), and N,N,N,N-tetramethylguanidinium triflate (TMGTf) were found useful as catalyst solvents for controlled 3-indolylation of isatins. Our investigation revealed that the reaction between isatin and indoles in [BMIM][BF4]-LiCl or TMGTf media stops at the step of addition of the two components providing 3-indolyl-3-hydroxyindolin-2-ones while the ionic liquid TMGT runs the reaction further through accompanying Friedel-Crafts substitution to afford symmetrical 3,3-di(indol-3-yl)indolin-2-ones. To take advantage of the difference between the effects of these ionic liquids on?the reaction progress, we planned a two-step protocol for the efficient synthesis of unsymmetrical 3,3-di(indol-3-yl)indolin-2-ones.