3335-90-8

Usage

Chemical compound

3-(4-chlorobenzylidene)-1,3-dihydro-2H-indol-2-one

Physical properties

yellow to brown crystalline powder

Uses

synthesis of pharmaceuticals and organic compounds

Properties

potential antitumor and antimicrobial properties

Applications

key intermediate in the development of bioactive compounds
Versatile reactivity and structural features
Used as a building block in the synthesis of heterocyclic compounds
Potential applications in the pharmaceutical and chemical industries

Upstream product

• 59-48-3 2-oxoindole 
• 104-88-1 4-chlorobenzaldehyde 
• 16327-29-0 2-indolinone 
• 91-56-5 indole-2,3-dione 

Downstream Products

• 1286738-51-9 (2'R,3S,4'R,5'R)-methyl 2',4'-bis(4-chlorophenyl)-2-oxospiro[indoline-3,3'-pyrrolidine]-5'-carboxylate 
• 3335-91-9 (E)-ethyl 2-(1-methyl-2-oxoindolin-3-ylidene)acetate 
• 3335-91-9 (Z)-3-(4-chlorobenzylidene)-1-methylindolin-2-one 
• 3335-89-5 3-(4-chlorobenzyl)-1-methylindolin-2-one 
• 3335-91-9 3-(4-chloro-benzylidene)-1-methyl-1,3-dihydro-indol-2-one 

Relevant academic research and scientific papers

Organocatalyzed one-pot three-component synthesis of novel 2-((2-hydroxy-1H-indol-3-yl)(phenyl)methyl)-2,3-dihydrophthalazine-1,4-diones

A new, simple and efficient one-pot three-component synthesis of oxindole derivatives has been developed by the reaction of phthalhydrazide, aldehydes and indoline-2-one under reflux conditions. This protocol avoids the use of expensive catalysts, toxic solvents and chromatographic techniques. Excellent yields, shorter reaction time, readily available starting materials and mild reaction condition are the advantages of this method. All synthesized compounds were characterized by 1H NMR, 13C NMR and mass spectroscopy.

Oxidative electro-organic synthesis of dimeric hexahydropyrrolo-[2,3-: B] indole alkaloids involving PCET: Total synthesis of (±)-folicanthine

An efficient electrochemical oxidation strategy for the total synthesis of a dimeric hexahydropyrrolo[2,3-b]indole alkaloid, (±)-folicanthine (1b), has been envisioned. Control experiments suggest that a PCET pathway involving stepwise electron transfer f

A facile synthesis of novel polycyclic spiropyrrolidine oxindoles incorporating the 1,3-dipolar cycloaddition of azomethine ylides

This study describes the synthesis of novel polycyclic spiropyrrolidine oxindoles through the 1,3-dipolar cycloaddition of azomethine ylides generated in situ with 3-(arylmethylene)-indolin-2-ones. Effect of substituents of azomethine ylides and various d

Photoredox asymmetric catalytic enantioconvergent substitution of 3-chlorooxindoles

An enantioconvergent substitution of 3-substituted 3-chlorooxindoles with N-aryl glycines under visible light irradiation is reported. A transition-metal-free cooperative catalysis platform with a dicyanopyrazine-derived chromophore (DPZ) as a photoredox catalyst and a chiral Br?nsted acid catalyst is effective for these transformations, which involve a single-electron transfer redox step and an enantioselective radical coupling. A variety of valuable chiral 3-aminomethylene-3-substituted oxindoles can be directly synthesized with high yields and enantioselectivities.

Facile synthesis of pyrroloindoles: Via a rhodium(II)-catalyzed annulation of 3-benzylidene-indolin-2-ones and α-imino carbenes

The annulation of 3-benzylidene-indolin-2-ones with α-imino rhodium carbenes generated in situ from N-sulfonyl-1,2,3-triazoles is presented. Through the appropriate choice of catalyst, the reactions can be reasonably modulated, and consequently, a number of pyrroloindole derivatives were constructed in moderate to excellent yields.

Synthesis of new class of spirocarbocycle derivatives by multicomponent domino reaction and their evaluation for antimicrobial, anticancer activity and molecular docking studies

A series of 25 new spirocarbocycles were synthesized by a three component reaction that involves few cyclic nucleophiles, vinyl malononitriles and aldehydes with variable substitution patterns. All the synthesized compounds were evaluated for their antimi

One-step synthesis of highly functionalized monofluorinated cyclopropanes from electron-deficient alkenes

The unique combination of Zn/LiCl allowed generation of reactive zinc enolate from ethyl dibromofluoroacetate. This fluorinated enolate reacts efficiently with a wide range of functionalized electron-deficient alkenes to afford the corresponding monofluorinated cyclopropylcarboxylates in good yields.

A Facile Method for the Synthesis of 3-Alkyloxindole

Benzylamine in combination with acetic acid was identified as a powerful catalyst for the condensation of oxindole with aldehydes, acetone or cyclic ketones. A variety of 3-alkyloxindoles could be readily prepared in 10 mmol scale via the sequential benzylamine acetate catalyzed condensation of oxindoles with aldehydes (or ketones) and conjugate reduction by NaBH4.

Identification of indoline-2-thione analogs as novel potent inhibitors of α-melanocyte stimulating hormone induced melanogenesis

Based on the hits, 3,4-dihydroquinazoline-2-thione (1) and benzimidazole-2-thione (2), a series of indole-2-thione (3) and indole-2-thiol inhibitors (4) of melanogenesis were designed, synthesized and evaluated in melanoma B16 cells under the stimulant of α-melanocyte stimulating hormone (α-MSH). The indole-2-thione compounds (3a-g) exhibited an effective inhibitory activity on melanin synthesis. The Structure-Activity Relationship (SAR) studies of 2 have revealed that in potent inhibitor 3a (>100% inhibition at 30μM, IC50=1.40μM) the role of nitrogen (3-N) at 3-position is insignificance. In addition, the hydrophobic substituents of 3 were better than the hydrophilic one. However, conversion of thione (-C=S, 3) to thiol (-C-SH, 4) led to decrease in the potency.

Highly enantioselective and organocatalytic α-amination of 2-Oxindoles

Figur Presented An effective method for the asymmetric synthesis of 3-amino-2-oxindoles was developed. The tetrasubstituted chiral carbon center was generated by asymmetric amination of N-unprotected 2-oxindoles with azodicarboxylate catalyzed by commercial biscinchona alkaloids in good to excellent yields with high enantioselectivities.