59816-56-7

Usage

Derivative of indole

Heterocyclic organic compound
2-(3,4-Dimethoxy-phenyl)-1H-indole is derived from the base structure of indole, which is a heterocyclic organic compound containing a benzene ring attached to a pyrrole ring.

Presence of phenyl ring

Aromatic structure
The compound contains a phenyl ring, which is a six-membered carbon ring with alternating single and double bonds, known for its stability and aromatic properties.

Methoxy groups at positions 3 and 4

Substitution on phenyl ring
Two methoxy groups (-OCH3) are attached to the phenyl ring at the 3rd and 4th positions, which can influence the compound's chemical reactivity and properties.

Indole ring system

Bicyclic structure
The compound features an indole ring system, which consists of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Use in scientific research

Precursor in synthesis
2-(3,4-Dimethoxy-phenyl)-1H-indole is used as a starting material or precursor in the synthesis of other organic compounds, allowing for the creation of various derivatives with different properties and applications.

Potential applications in pharmaceutical and medicinal chemistry

Unique structural properties
Due to its distinct structure, 2-(3,4-dimethoxy-phenyl)-1H-indole may have potential uses in the development of pharmaceuticals and medicines, although further research is needed to explore these possibilities.

Upstream product

• 58697-62-4 N-[1-(3,4-dimethoxy-phenyl)-ethylidene]-N'-phenyl-hydrazine 
• 615-43-0 2-iodophenylamine 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 59-88-1 phenylhydrazine hydrochloride 
• 610-66-2 2-nitro-benzeneacetonitrile 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 1314247-90-9 4-((2-bromophenyl)ethynyl)-1,2-dimethoxybenzene 
• 100-63-0 phenylhydrazine 

Downstream Products

• 1463045-57-9 3-(3,4-dimethoxyphenyl)-3-hydroxy-1,3-dihydro-2H-indol-2-one 
• 1402604-37-8 2-(3,4-dimethoxyphenyl)-3,3-difluoro-3H-indole 
• 94005-26-2 1-[2-(3,4-dimethoxy-phenyl)-indol-3-yl]-ethanone 
• 1309945-79-6 C₃₄H₃₀N₂O₄ 
• 74625-86-8 2-(3,4-dimethoxyphenyl)-1-oxy-indol-3-one 
• 94309-18-9 [2-(3,4-dimethoxy-phenyl)-indol-3-ylmethyl]-dimethyl-amine 

Relevant academic research and scientific papers

Modular counter-Fischer?indole synthesis through radical-enolate coupling

A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.

Nickel-Catalyzed Intramolecular Direct Arylation of Imines toward Diverse Indoles

An efficient nickel-catalyzed intramolecular direct arylation of imines with challenging aryl chlorides has been developed. The versatile nickel catalysis made use of easily accessible imines and delivered diversely decorated 2-arylindoles of considerable importance to biological and medicinal chemistry.

Nickel-Catalyzed Intramolecular Direct Arylation of Imines toward Diverse Indoles

An efficient nickel-catalyzed intramolecular direct arylation of imines with challenging aryl chlorides has been developed. The versatile nickel catalysis made use of easily accessible imines and delivered diversely decorated 2-arylindoles of considerable importance to biological and medicinal chemistry.

Synthesis and biological evaluation of 2-(2'/3'/4'/6'-substituted phenyl)-1hindoles

Objective: Indole derivatives were reported to a wide range of biological activities. Thus it was our aim to synthesize a series of 2-(2'/3'/4'/6'- substituted phenyl) -1H-indoles using clayzic catalyst and screen for their in vitro anti-inflammatory, antioxidant and antimicrobial activities. Methods: Various substituted acetophenones were reacted with phenylhydrazine in the presence of modified clayzic catalyst and obtained 2- (2'/3'/4'/6'-substituted phenyl)-1H-indoles in a one pot reaction. The cyclized compounds were characterized by FT-IR, NMR, UV-Vis and mass spectral analyses and screened for anti-inflammatory activity against cytokines tumor necrosis factor (TNF-α) and interleukin-6 (IL-6) by measuring cytokine production by performing sandwich ELISA model, antioxidant activity by DPPH assay method and antimicrobial activity by well-diffusion method. Results: An eco-friendly route with better yields for the synthesis of 2-(2'/3'/4'/6'-substituted phenyl)-1H-indoles in the presence of clayzic catalyst was achieved. The biological activity results suggested that compounds (2d, 2e and 2i) have excellent anti-inflammatory activity, compounds (2a-2d and 2j) possessing better antioxidant property and compounds (2b, 2i, 2k and 2m) have promising antibacterial and antifungal activities when compared to the standard drugs. Conclusion: Synthesis of 2-(2'/3'/4'/6'-substituted phenyl)-1H-indoles was successfully achieved in the presence of clayzic catalyst. Compounds bearing amino, methyl, methoxy, hydroxyl and fluoro groups have shown better anti-inflammatory, antioxidant and antimicrobial activities when compared to the other compounds and 1H-indole.

Synthesis and antioxidant properties of substituted 2-phenyl-1H-indoles

In this study, we report the design, synthesis and antioxidant activity of a series of substituted 2-(4-aminophenyl)-1H-indoles and 2-(methoxyphenyl)-1H- indoles. The new compounds are structurally related to the known indole-based antioxidant lead compou

Pd-Catalyzed cascade reaction for the synthesis of 2-substituted indoles

An efficient cascade methodology toward the synthesis of 2-substituted indoles has been developed. The transformation proceeds via a palladium-catalyzed cross-coupling reaction of o-nitrobenzyl cyanides with boronic acids. The use of Fe as co-catalyst during the course of reaction employs significant enhancement in reaction rates. The developed protocol allows for the unprecedented use of arylboronic acids as coupling partners for constructing 2-substituted indoles.

Pd-Catalyzed cascade reaction for the synthesis of 2-substituted indoles

An efficient cascade methodology toward the synthesis of 2-substituted indoles has been developed. The transformation proceeds via a palladium-catalyzed cross-coupling reaction of o-nitrobenzyl cyanides with boronic acids. The use of Fe as co-catalyst during the course of reaction employs significant enhancement in reaction rates. The developed protocol allows for the unprecedented use of arylboronic acids as coupling partners for constructing 2-substituted indoles. Georg Thieme Verlag Stuttgart · New York.

Palladium-catalyzed synthesis of indoles via ammonia cross-coupling-alkyne cyclization

The synthesis of indoles via the metal-catalyzed cross-coupling of ammonia is reported for the first time; the developed protocol also allows for the unprecedented use of methylamine or hydrazine as coupling partners. These Pd/Josiphos-catalyzed reactions proceed under relatively mild conditions for a range of 2-alkynylbromoarenes.

Oxygenation of 2,3-dihydroindoles

Isatogens (3-oxo-3H-indole 1-oxides) possess interesting biological properties and development of a general method to construct these derivatives has now been developed. Indolines (2,3-dihydroindoles) and isatogens have been prepared in an efficient route starting from indoles substituted in position 2. Reduction of the 2-substituted indoles was performed with tin and hydrochloric acid to give racemic indolines, which were converted to isatogens by 3-chloroperoxybenzoic acid (m-CPBA).