89096-73-1

Usage

Structure

A derivative of pyrrole, a heterocyclic aromatic organic compound, containing a pyrrole ring with a methoxyphenyl group attached at the 1-position.

Synthesis

Can be synthesized through various methods.

Use

Used in research and development as a building block for the synthesis of other organic compounds.

Value

Unique structure and properties make it valuable for creating new materials and pharmaceuticals.

Upstream product

• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 90-04-0 2-methoxy-phenylamine 
• 6117-80-2 1,4-butenediol 
• 91-23-6 2-Nitroanisole 
• 109-97-7 pyrrole 
• 578-57-4 2-bromoanisole 
• 529-28-2 4-iodoanisol 
• 51-35-4 4R-4-hydroxyproline 

Downstream Products

• 32277-91-1 2-(1H-pyrrol-1-yl)phenol 
• 158966-71-3 3-Chloro-1-(2-methoxy-phenyl)-1H-pyrrole 
• 158966-70-2 2-Chloro-1-(2-methoxy-phenyl)-1H-pyrrole 
• 169036-73-1 1-(2-methoxy-phenyl)-1H-pyrrole-2-carbaldehyde 
• 864547-99-9 1-(2-methoxy-phenyl)-1H-pyrrole-3-carbaldehyde 

Relevant academic research and scientific papers

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.

BN/BO-Ullazines and Bis-BO-Ullazines: Effect of BO Doping on Aromaticity and Optoelectronic Properties

We have achieved substitutional doping of ullazine with either two BO units or with one BO unit and one BN unit. The synthesis of these B-doped ullazines is straightforward, using demethylation and borylative cyclization as the key steps. Ullazine cores o

Cu(II)-catalyzed C-N coupling of (hetero)aryl halides and N-Nucleophiles promoted by α-benzoin oxime

We first reported the new application of a translate metal chelating ligand α-benzoin oxime for improving Cu-catalyzed C-N coupling reactions. The system could catalyse coupling reactions of (hetero)aryl halides with a wide of nucleophiles (e.g., azoles, piperidine, pyrrolidine and amino acids) in moderate to excellent yields. The protocol allows rapid access to the most common scaαolds found in FDA-approved pharmaceuticals.

Methyl-α-d-glucopyranoside as Green Ligand for Selective Copper-Catalyzed N-Arylation

In the selective N-arylation of amines or azoles with aryl halidesa-, methyl-α-d-glucopyranoside (MG) was found to function as a green ligand of copper powder. In addition, nitrogen heterocyclic amine compounds can also undergo the N-arylation coupling with heterocyclic aryl chlorides. This process allows access to a variety of aromatic amines and aryl azoles under mild reaction conditions, has good tolerance, and proceeds in moderate to high yield.

Nickel-Catalyzed Synthesis of N-Substituted Pyrroles Using Diols with Aryl- and Alkylamines

Herein, nickel-catalyzed sustainable strategy for the synthesis of N-substituted pyrroles using butene-1,4-diols and butyne-1,4-diols with a series of aryl-, alkyl-, and heteroarylamines is reported. The catalytic protocol is tolerant of free alcohol, halide, alkyl, alkoxy, oxygen heterocycles, activated benzyl, and the pyridine moiety and resulted in up to 90% yield. Initial mechanistic studies involving defined nickel catalyst, determination of rate, and order of reaction including deuterium-labeling experiments were performed for pyrrole synthesis.

Unveiling the Biocatalytic Aromatizing Activity of Monoamine Oxidases MAO-N and 6-HDNO: Development of Chemoenzymatic Cascades for the Synthesis of Pyrroles

A chemoenzymatic cascade process for the sustainable production of pyrroles has been developed. Pyrroles were synthesized by exploiting the previously unexplored aromatizing activity of monoamine oxidase enzymes (MAO-N and 6-HDNO). MAO-N/6-HDNO whole cell biocatalysts are able to convert 3-pyrrolines into pyrroles under mild conditions and in high yields. Moreover, MAO-N can work in combination with the ruthenium Grubbs catalyst, leading to the synthesis of pyrroles from diallylamines/-anilines in a one-pot cascade metathesis-aromatization sequence.

Sustainable Pathways to Pyrroles through Iron-Catalyzed N-Heterocyclization from Unsaturated Diols and Primary Amines

Pyrroles are prominent scaffolds in pharmaceutically active compounds and play an important role in medicinal chemistry. Therefore, the development of new, atom-economic, and sustainable catalytic strategies to obtain these moieties is highly desired. Direct catalytic pathways that utilize readily available alcohol substrates have been recently established; however, these approaches rely on the use of noble metals such as ruthenium or iridium. Here, we report on the direct synthesis of pyrroles using a catalyst based on the earth-abundant and inexpensive iron. The method uses 2-butyne-1,4-diol or 2-butene-1,4-diol that can be directly coupled with anilines, benzyl amines, and aliphatic amines to obtain a variety of N-substituted pyrroles in moderate-to-excellent isolated yields.

An efficient heterogeneous catalytic method for the N-arylation of pyrrole and other N-heterocycles

Abstract 4 ? molecular sieve modified with copper(0) or copper(II) is an efficient heterogeneous catalyst for the arylation of pyrrole and some other heterocycles with iodo- or bromoarenes, Cs2CO3 base and pyrrole (or DMF) solvent. The catalysts can be easily prepared and are reusable.

L-(+)-Tartaric acid and choline chloride based deep eutectic solvent: An efficient and reusable medium for synthesis of N-substituted pyrroles via Clauson-Kaas reaction

l-(+)-Tartaric acid-choline chloride based deep eutectic solvent has been found to be an effective promoted medium for Clauson-Kaas reaction of aromatic amines and 2,5-dimethoxytetrahydrofuran. Structurally diverse N-substituted pyrroles were obtained in high to excellent yields under mild conditions. The deep eutectic solvent is inexpensive, non-toxic, reusable and biodegradable.

New pyrrole derivatives with potent tubulin polymerization inhibiting activity as anticancer agents including hedgehog-dependent cancer

We synthesized 3-aroyl-1-arylpyrrole (ARAP) derivatives as potential anticancer agents having different substituents at the pendant 1-phenyl ring. Both the 1-phenyl ring and 3-(3,4,5-trimethoxyphenyl)carbonyl moieties were mandatory to achieve potent inhi