851-33-2

Usage

Class

Aromatic compounds

Subclass

Pyrroles

Characterization

Five-membered ring containing four carbon atoms and one nitrogen atom

Color

Dark red-brown

Solubility

Insoluble in water

Usage

Building block in the synthesis of organic materials

Applications

Conducting polymers, optical materials, optoelectronic devices, pharmaceuticals

Additional properties

Antimicrobial and antifungal properties

Potential applications

Medical and agricultural uses

Upstream product

• 142-04-1 aniline hydrochloride 
• 62-53-3 aniline 
• 495-71-6 phenacylacetophenone 
• 14062-91-0 (N-benzoyl-anilino)-phenyl-acetonitrile 
• 5044-52-0 vinyltriphenylphosphonium bromide 
• 1749-19-5 N-(1-phenylethylidene)aniline 
• 952009-23-3 2,5-bis-(2-carboxy-phenyl)-1-phenyl-pyrrole 
• 5883-81-8 2-anilinoacetophenone 
• 63302-05-6 phenylammonium formate 
• 959-28-4 1,4-diphenylbut-2-ene-1,4-dione 
• 1087-09-8 1,4-diphenyl-but-2-yne-1,4-dione 
• 113385-73-2 N,N-bis(phenacyl)-4-methylaniline 
• 98-86-2 acetophenone 
• 536-74-3 phenylacetylene 

Downstream Products

• 111029-28-8 3-nitro-1,2,5-triphenyl-1H-pyrrole 
• 102662-56-6 3,4-dinitro-1,2,5-triphenyl-pyrrole 
• 188483-20-7 5-benzoyl-3-phenylisothiazole 
• 2987-77-1 triethylphenylsilane 
• 1456622-55-1 1,1',2,2',5,5'-hexaphenyl-1H,1'H-3,3'-bipyrrole 
• 130850-69-0 3,4-Dibromo-1,2,5-triphenyl-1H-pyrrole 
• 15345-47-8 1,2,3,5-tetraphenyl-pyrrole 
• 1259363-45-5 C₂₂H₁₆BrN 

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.

Cascade Synthesis of Pyrroles from Nitroarenes with Benign Reductants Using a Heterogeneous Cobalt Catalyst

A bifunctional 3d-metal catalyst for the cascade synthesis of diverse pyrroles from nitroarenes is presented. The optimal catalytic system Co/NGr-C@SiO2-L is obtained by pyrolysis of a cobalt-impregnated composite followed by subsequent selective leaching. In the presence of this material, (transfer) hydrogenation of easily available nitroarenes and subsequent Paal–Knorr/Clauson-Kass condensation provides >40 pyrroles in good to high yields using dihydrogen, formic acid, or a CO/H2O mixture (WGSR conditions) as reductant. In addition to the favorable step economy, this straightforward domino process does not require any solvents or external co-catalysts. The general synthetic utility of this methodology was demonstrated on a variety of functionalized substrates including the preparation of biologically active and pharmaceutically relevant compounds, for example, (+)-Isamoltane.

Copper-catalyzed pyrrole synthesis from 3,6-dihydro-1,2-oxazines

Highly-functionalized pyrroles could be effectively synthesized from 3,6-dihydro-1,2-oxazines using a heterogeneous copper on carbon (Cu/C) under neat heating conditions. Furthermore, the in situ formation of 3,6-dihydro-1,2-oxazines via the hetero Diels-Alder reaction between nitroso dienophiles and 1,3-dienes and the following Cu/C-catalyzed pyrrole synthesis also provided the corresponding pyrrole derivatives in a one-pot manner.

s-Block-Metal-Mediated Hydroamination of Diphenylbutadiyne with Primary Arylamines Using a Dipotassium Tetrakis(amino)calciate Precatalyst

(Chemical Equation Presented). The hydroamination of diphenylbutadiyne with primary arylamines requires a reactive catalyst. In the presence of heterobimetallic K2[Ca{N(H)Dipp}4] (Dipp = 2,6-diisopropylphenyl) the performance of this

Copper(II)-Promoted, One-Pot Conversion of 1-Alkynes with Anhydrides or Primary Amines to the Respective 2,5-Disubstituted Furans or Pyrroles under Microwave Irradiation Conditions

Furans and pyrroles are prepared from 1-alkynes by using a Cu(II)-promoted, one-pot, microwave irradiation method. Glaser coupling of 1-alkynes and cyclization of the resulting 1,3-diyne in the presence of an anhydride or a primary amine results in the formation of the respective 2,5-diaryl- or 2,5-dialkyl-substituted furans and pyrroles.

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.

Organic synthesis in deep eutectic solvents: Paal-Knorr reactions

Deep eutectic solvents (the combination of either urea or glycerol with choline chloride) are effective solvents/catalysts for Paal-Knorr reactions to form pyrroles of furans. The reaction conditions are quite mild and do not require the addition of an additional Bronsted or Lewis acid catalyst. Given the inexpensive, non-toxic, and recyclable nature of the DES, these reaction conditions are simple and highly environmentally friendly.

Synthesis of 2,5-diarylpyrroles by ligand-free palladium-catalyzed ch activation of pyrroles in ionic liquids

The palladium-catalyzed CH activation and arylation of N-methylpyrrole and N-phenylpyrrole allowed a convenient synthesis of diarylpyrroles. The reactions were performed by using tetrabutylammonium acetate as an ionic solvent, which allowed for the application of a ligand-free catalytic system by using simple palladium salts or polyvinylpyrrolidone-stabilized palladium nanoparticles as the catalyst.

Xanthan sulfuric acid as an efficient, green, biodegradable, and recyclable solid acid catalyst for one-pot synthesis of N-substituted pyrroles under solvent-free conditions at room temperature

A new, green, and efficient method for synthesis of a variety of N-substituted pyrroles from condensation reactions of 2,5-hexanedione with amines or diamines using xanthan sulfuric acid as a biosupported and reusable ecofriendly catalyst under solvent-free conditions at room temperature is described. The use of a nontoxic, inexpensive, easily available, and reusable biosupported proton source catalyst under solvent-free conditions makes this protocol practical, environmentally friendly, and economically attractive.

Polystyrene-supported GaCl3 as a highly efficient and recyclable heterogeneous Lewis acid catalyst for one-pot synthesis of N-substituted pyrroles

A new and environmentally benign method for the preparation of N-substituted pyrroles from one-pot condensation reaction of 2,5-hexanedione with amines and diamines in the presence of polystyrene-supported gallium trichloride (PS/GaCl3) as a highly active and reusable heterogeneous Lewis acid catalyst is presented. This new protocol has the advantages of easy availability, stability, reusability and eco-friendly of the catalyst, high to excellent yields, simple experimental and work-up procedure.