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Usage

Heterocyclic compound

A compound that contains a five-membered ring with four carbon atoms and one nitrogen atom.

Contains phenyl and 4-methoxyphenyl groups

The presence of these groups makes the compound important for pharmaceutical and chemical applications.

Potential biological activities

The compound has been studied for its potential medicinal properties and is used in research for the development of new drugs and pharmaceuticals.

Valuable building block for synthesizing complex organic molecules

The unique chemical structure of the compound makes it useful for creating complex organic molecules.

Upstream product

• 104-94-9 4-methoxy-aniline 
• 495-71-6 phenacylacetophenone 
• 72867-36-8 (N-benzoyl-p-anisidino)-phenyl-acetonitrile 
• 5044-52-0 vinyltriphenylphosphonium bromide 
• 886-66-8 1,4-diphenyl-1,3-butadiyne 
• 536-74-3 phenylacetylene 
• 98-86-2 acetophenone 
• 2743-00-2 (E)-4-methoxy-N-(1-phenylethylidene)benzenamine 

Downstream Products

• 188483-20-7 5-benzoyl-3-phenylisothiazole 
• 853-38-3 1-(4-hydroxyphenyl)-2,5-diphenyl-1H-pyrrole 
• 877-68-9 4-trimethylsilylanisole 
• 13132-25-7 4-(trimethylsilyl)phenol 
• 1456622-60-8 1,1'-bis(4-methoxyphenyl)-2,2',5,5'-tetraphenyl-3,3'-bipyrrole 

Relevant academic research and scientific papers

Generation of Aryllithium Reagents from N -Arylpyrroles Using Lithium

Treatment of 1-aryl-2,5-diphenylpyrroles with lithium powder in tetrahydrofuran at 0 °C results in the generation of the corresponding aryllithium reagents through reductive C-N bond cleavage.

The Paal-Knorr reaction revisited. A catalyst and solvent-free synthesis of underivatized and N-substituted pyrroles

A new, modified synthesis of pyrroles is described. The reaction of 2,5-hexandione with a variety of amines yielded the expected pyrrole analogues in excellent yields. The reactions were carried out under the ultimate green conditions excluding both catalyst and solvent applying simple stirring at room temperature. The variety of amines include aqueous ammonium hydroxide for the synthesis of pyrroles with a free NH group, and benzylamines, anilines and phenylene-diamines for the synthesis of several N-derivatized pyrroles. The reaction also occurs efficiently with a variety of 1,4-diketones, although the reaction rates and yields are lower for the diketones that do not possess terminal methyl group(s). This journal is

A general approach to arylated furans, pyrroles, and thiophenes

A general and practical synthetic method for aryl-substituted five-membered heterocycles has been developed. In the presence of KOH (30%), 1,4-diaryl-1,3-butadiynes undergo the cyclocondensation reaction with water, primary amines, and Na2S·9H2O in DMSO at 80 °C to afford 2,5-diarylfurans, 1,2,5-trisubstituted pyrroles, and 2,5-diarylthiophenes in good to high yields. Further studies have disclosed that aryl-substituted five-membered heterocycles can be also synthesized by a one-pot, two-step strategy from the terminal alkynes in DMSO firstly catalyzed by CuCl, and then via addition of KOH to promote the cyclocondensation of 1,3-butadiynes generated in situ.

Diaryl- and triaryl-pyrrole derivatives: Inhibitors of the MDM2-p53 and MDMX-p53 protein-protein interactions

Screening identified 2-(3-((4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)- ylidene)methyl)-2,5-dimethyl-1H-pyrrol-1-yl)-4,5,6,7-tetrahydrobenzo[b] thiophene-3-carbonitrile as an MDM2-p53 inhibitor (IC50 = 12.3 μM). MDM2-p53 and MDMX-p53 activity was seen for 5-((1-(4-chlorophenyl)-2,5- diphenyl-1H-pyrrol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (MDM2 IC50 = 0.11 μM; MDMX IC50 = 4.2 μM) and 5-((1-(4-nitrophenyl)-2,5-diphenyl-1H-pyrrol-3-yl)methylene)pyrimidine-2,4,6(1H, 3H,5H)-trione (MDM2 IC50 = 0.15 μM; MDMX IC50 = 4.2 μM), and cellular activity consistent with p53 activation in MDM2 amplified cells. Further SAR studies demonstrated the requirement for the triarylpyrrole moiety for MDMX-p53 activity but not for MDM2-p53 inhibition. The Royal Society of Chemistry.

CuCl-catalyzed cycloaddition of 1,3-butadiynes with primary amines: An atom-economic process for synthesis of 1,2,5-trisubsituted pyrroles

1,3-Butadiynes underwent inter- and intramolecular double hydroamination with primary amines in the presence of CuCl at 100°C to afford 1,2,5-trisubsituted pyrroles in good to high yields.

A straightforward highly efficient Paal-Knorr synthesis of pyrroles

A straightforward simple synthesis of substituted pyrroles using bismuth nitrate-catalyzed modified Paal-Knorr method has been accomplished with an excellent yield. This method produces pyrroles with multicyclic aromatic amines.

Conversion of pyrroles into bi-1,2,5-thiadiazoles: A new route to biheterocycles

Trithiazyl trichloride 1 converts 1,2,5-triphenylpyrrole 5 into its 3,4-dichloro derivative together with the isothiazole imine 6 and the imine hydrolysis product, the ketone 3. The best yield of the isothiazole 6 is obtained in the presence of 4 A molecular sieves (Table 1). Conversion of the pyrrole 5 into the isothiazole 6 is exactly analogous to the reaction of 1 with 2,5-diphenyl-furan and -thiophene. Other N-aryl and the related 2,5-diphenylpyrroles 8 give similar results (Table 2). However, 1-methyl-2,5-diphenylpyrrole 11 reacts with 1 in an entirely different way to give 4,4′-diphenyl-3,3′-bi-1,2,5-thiadiazole 12, in which two thiadiazole rings have been fused onto the pyrrole and the CH3N unit has been excised as HCN. The same product 12 is formed, in similar yields, by reaction of 1 with 1,4-diphenylbuta-1, 3-diyne and 1,4-diphenylbut-1-en-3-yne. Other N-alkyl 2,5-diphenylpyrroles 16 react similarly (Table 3), giving the best yield (70%) of bi-thiadiazole 12 in the presence of 4 A molecular sieves (Table 4). 1-Methyl- and 1-ethyl-3,4-dibromo-2,5-diphenylpyrrole also give 12, together with 3-(benzoyldichloromethyl)-4-phenyl-1,2,5-thiadiazole 21 in high combined yield. The formation of bi-1,2,5-thiadiazole 12 from N-alkylpyrroles represents a new dissection of the pyrrole ring and a new and very short route to an aromatic biheterocyclic system. Mechanisms which rationalise the different pathways observed are proposed for all of these reactions.

Synthesis of Substituted Pyrroles by Intramolecular Condensation of a Wittig Reagent with the Carbonyl Group of a Tertiary Amide

1,2,5-Trisubstituted pyrroles are obtained in 50-100percent yields by addition of the conjugate bases of open-chain analogues of Reissert compounds to the vinyltriphenylphosphonium cation, with subsequent cyclization by an intramolecular Wittig reaction and base-catalyzed elimination of hydrogen cyanide.