188953-77-7

Usage

Structure

A heterocyclic compound with a five-membered ring containing one nitrogen atom and a 3-methoxyphenyl group as a substituent.

Derivative

Of pyrrole.

Aromatic ring

Present due to the 3-methoxyphenyl group.

Methoxy substituent

Adds unique chemical and physical properties to the compound.

Potential applications

Pharmaceutical and agrochemical industries as a building block for the synthesis of biologically active molecules.

Research and development

Used as a reference standard for analytical techniques such as mass spectrometry and NMR spectroscopy.

Organic dyes and pigments

Aromatic nature may make it useful as a component in their synthesis.

Upstream product

• 109-97-7 pyrrole 
• 2398-37-0 3-methoxyphenyl bromide 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 536-90-3 m-Anisidine 
• 766-85-8 3-methoxy-1-iodobenzene 
• 51-35-4 4R-4-hydroxyproline 
• 555-03-3 3-nitroanisole 
• 3908-66-5 tris(3-methoxyphenyl) phosphate 
• 6117-80-2 1,4-butenediol 

Relevant academic research and scientific papers

Copper-catalysed N-arylation of pyrrole with aryl iodides under ligand-free conditions

A simple, inexpensive and ligand-free copper-catalysed N-arylation of pyrrole with aryl iodides has been developed giving N-arylated products in moderate to excellent yields. The catalyst loading is relative low (5 mol%) and the catalyst system was stable in air.

A facile synthesis of diaryl pyrroles led to the discovery of potent colchicine site antimitotic agents

Three different series of cis-restricted analogues of combretastatin A-4 (CA-4), corresponding to thirty-nine molecules that contained a pyrrole nucleus interposed between the two aryl rings, were prepared by a palladium-mediated coupling approach and evaluated for their antiproliferative activity against six human cancer cell lines. In the two series of 1,2-diaryl pyrrole derivatives, results suggested that the presence of the 3′,4′,5′-trimethoxyphenyl moiety at the N-1 position of the pyrrole ring was more favorable for antiproliferative activity. In the series of 3,4-diarylpyrrole analogues, three compounds (11i-k) exhibited maximal antiproliferative activity, showing excellent antiproliferative activity against the CA-4 resistant HT-29 cells. Inhibition of tubulin polymerization of selected 1,2 pyrrole derivatives (9a, 9c, 9o and 10a) was similar to that observed with CA-4, while the isomeric 3,4-pyrrole analogues 11i-k were generally from 1.5- to 2-fold more active than CA-4. Compounds 11j and 11k were the only compounds that showed activity as inhibitors of colchicine binding comparable to that CA-4. Compound 11j had biological properties consistent with its intracellular target being tubulin. This compound was able to block the cell cycle in metaphase and to induce significant apoptosis at a concentration of 25 nM, following the mitochondrial pathway, with low toxicity for normal cells. More importantly, compound 11j exerted activity in vivo superior to that of CA-4P, being able to significantly reduce tumor growth in a syngeneic murine tumor model even at the lower dose tested (5.0 mg/kg).

Functionalized multi-walled carbon nanotubes as an efficient reusable heterogeneous catalyst for green synthesis of N-substituted pyrroles in water

In this protocol, the functionalization of multi-walled carbon nanotubes (MWCNTs) was carried out and the resulting sulfonated MWCNTs were characterized by FT-IR, XRD, SEM, BET, EDX, XPS and Raman spectroscopy that are each discussed separately in the text. Then, the MWCNT-SO3H composite was applied as an efficient, recyclable heterogeneous catalyst for the synthesis of N-substituted pyrroles via the reaction of 2,5-dimethoxy tetrahydrofuran with primary amines under clean and mild conditions. In this reaction, the N-substituted pyrroles were obtained as beneficial and significant products in short reaction times (30-65 min) and good to excellent yields (40-92%) with high purity. The products were obtained through a simple work up procedure and characterized by FT-IR, 1H NMR and 13C NMR. After the end of the reaction, the nanocatalyst was recovered and reused several times without efficient loss of its activity for the preparation of N-substituted pyrroles.

Pd/Cu-catalyzed dual C-H bond carbonylation towards the synthesis of fluorazones

Pd/Cu catalyzed oxidative dual C-H bond activation/carbonylation still remains a great challenge due to the generation of by-products via C-C bond formation. Herein we developed a straightforward Pd/Cu-catalyzed oxidative dual C-H bond carbonylation process to access biologically and pharmaceutically important fluorazones from easily available N-aryl pyrroles and CO. A wide range of functional groups were well tolerated in this transformation, and O2 could be utilized as the only terminal oxidant to promote the oxidative carbonylation process.

Utilization of caffeine carbon supported cobalt catalyst in the tandem synthesis of pyrroles from nitroarenes and alkenyl diols

Employing bio-waste caffeine carbon-supported heterogeneous cobalt catalyst, synthesis of various substituted pyrrole derivatives is reported. In this methodology, pyrroles were synthesized through coupling between nitroarenes and alkenyl diols in a tandem manner. Among all the heterogeneous catalysts Co(OAc)2-CC-800 displayed the highest catalytic activity. Preparative scale synthesis of pyrroles and synthesis of anti-tubercular agent 5-(4-(1H-pyrrol-1-yl)phenyl)-1,3,4-oxadiazole-2-thiol revealed the practical applicability of this protocol. Several kinetic experiments and Hammett studies were conducted to understand the probable mechanism and electronic effects on this transformation.

Lactam derivatives and preparation method and application thereof

The invention relates to lactam derivatives and a preparation method and application thereof. Compared with the prior art, the invention provides lactam compounds with a novel structure. The compoundsand compositions thereof have remarkable activity in inhibition of the proliferation of cancer cells (including, but not limited to, the liver cancer cell line HepG2 and the lung cancer cell line A549), and the activity of multiple compounds is in the same order of magnitude as the activity of the commercial drug adriamycin or superior to the activity of adriamycin. The compounds of the inventioncan be prepared from N-substituted pyrrole compounds through a reaction, and the preparation method is convenient, rapid and efficient.

Palladium-catalyzed c(sp2)-n bond cross-coupling with triaryl phosphates

The first general palladium-catalyzed amination of aryl phosphates is described. The combination of MorDalPhos with [Pd(-cinnamyl)Cl]2 enables the amination of electron-rich, electron-neutral, and electron-poor aryl phosphates with a board range of aromatic, aliphatic, and heterocyclic amines. Common functional groups such as ether, keto, ester, and nitrile show an excellent compatibility in this reaction condition. The solvent-free amination reactions are also successful in both solid coupling partners. The gram-scale cross-coupling is achieved by this catalytic system.

Palladium-Catalyzed C(sp2)-N Bond Cross-Coupling with Triaryl Phosphates

The first general palladium-catalyzed amination of aryl phosphates is described. The combination of MorDalPhos with [Pd(?-cinnamyl)Cl]2 enables the amination of electron-rich, electron-neutral, and electron-poor aryl phosphates with a board range of aromatic, aliphatic, and heterocyclic amines. Common functional groups such as ether, keto, ester, and nitrile show an excellent compatibility in this reaction condition. The solvent-free amination reactions are also successful in both solid coupling partners. The gram-scale cross-coupling is achieved by this catalytic system.

Efficient and Mild Ullmann-Type N-Arylation of Amides, Carbamates, and Azoles in Water

A simple, sustainable, efficient, mild, and low-cost protocol was developed for d-glucose-assisted Cu-catalyzed Ullmann reactions in water for amides, carbamates, and nitrogen-containing heterocycles. The reaction was compatible with diverse aryl/heteroaryl iodides, giving highly substituted pyridine, indole, or indazole rings. This method offers an attractive alternative to existing protocols, because the reaction proceeds in aqueous media, occurs at or near ambient temperature, and provides the N-arylated products in good to high yields.

An elegant protocol for the synthesis of N-substituted pyrroles through C-N cross coupling/aromatization process using CuFe2O4 nanoparticles as catalyst under ligand-free conditions

A simple and efficient, ligand-free C-N cross-coupling of aryl halides/benzyl bromides with trans-4-hydroxy-l-proline has been developed to produce aromatized N-substituted pyrroles, using a catalytic amount of magnetically separable and recyclable CuFe2O4 nanoparticles, in the presence of Cs2CO3 in DMSO at 100 °C.