70487-19-3

Usage

Uses

Used in Pharmaceutical Development:
3-(4-methoxyphenyl)-2,5-diphenyl-1H-pyrrole is utilized as a key intermediate in the synthesis of pharmaceuticals due to its potential biological activities. Its unique structure allows for the development of new drugs targeting various therapeutic areas, including but not limited to cardiovascular, neurological, and anti-inflammatory applications.
Used in Material Science:
In the field of material science, 3-(4-methoxyphenyl)-2,5-diphenyl-1H-pyrrole is employed as a component in the creation of advanced materials. Its chemical properties make it suitable for use in the development of organic materials with specific electronic, optical, or mechanical properties, contributing to innovations in areas such as organic electronics, sensors, and polymers.
Used in Medicinal Chemistry Research:
3-(4-methoxyphenyl)-2,5-diphenyl-1H-pyrrole serves as a valuable compound in medicinal chemistry research. It is used as a starting material or a building block in the design and synthesis of novel bioactive molecules. Its presence in various drug discovery programs underscores its importance in the search for new therapeutic agents with improved efficacy and safety profiles.
Used in Chemical Synthesis:
As a versatile chemical intermediate, 3-(4-methoxyphenyl)-2,5-diphenyl-1H-pyrrole is used in the synthesis of a wide range of organic compounds. Its reactivity and functional groups make it an ideal candidate for various chemical reactions, facilitating the production of complex organic molecules for use in pharmaceuticals, agrochemicals, and other specialty chemicals.

Upstream product

• 959-33-1 3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 838-40-4 2,5-diphenyl-1H-pyrrole 
• 3179-10-0 1-methoxy-4-(2-nitro-vinyl)-benzene 
• 16483-98-0 2,3-diphenyl-2H-azirine 
• 495-71-6 phenacylacetophenone 
• 70-11-1 α-bromoacetophenone 
• 623-12-1 4-chloromethoxybenzene 
• 100-46-9 benzylamine 
• 16616-43-6 1-(4-methoxy-phenyl)-3-phenyl-propynone 
• 7380-78-1 4-(phenylethynyl)anisole 
• 57957-24-1 N-(1-phenylvinyl)acetamide 
• 29670-63-1 N-benzoyl-2-phenylglycine 
• 98-88-4 benzoyl chloride 

Downstream Products

• 51860-30-1 3-(4-methoxyphenyl)-3,5-diphenyl-1H-pyrrol-2(3H)-one 

Relevant academic research and scientific papers

Visible Light-Induced, Metal-Free Denitrative [3+2] Cycloaddition for Trisubstituted Pyrrole Synthesis

A metal-free, regioselective synthesis of trisubstituted pyrroles has been developed through a formal [3+2] cycloaddition reaction between 2H-azirines and nitroalkenes under visible light/photoredox-catalyzed conditions. The reaction proceeds through 2H-a

Synthesis of 2,2,5-Trisubstituted 2 H-Pyrroles and 2,3,5-Trisubstituted 1 H-Pyrroles by Ligand-Controlled Site-Selective Dearomative C2-Arylation and Direct C3-Arylation

Palladium-catalyzed site-selective dearomative C2-arylation of 2,5-diaryl-1H-pyrroles with aryl chlorides was accomplished, and a series of 2,2,5-triaryl-2H-pyrroles were synthesized. In addition, the site selectivity of the reaction was switched by simply changing the ligand, and the direct C3-arylated 2,3,5-triaryl-1H-pyrroles were prepared. The obtained 2,2,5-triaryl-2H-pyrroles could be further transformed into 2,2,5,5-tetraarylpyrrolidines.

Base-Promoted Oxidative Dearomatization of Pyrroles to 4-Pyrrolin-2-ones

A base-promoted oxidative dearomatization of substituted pyrroles for the synthesis of 3,3-disubstituted 4-pyrrolin-2-ones under mild reaction conditions is described. A cascade aerobic oxidation/semipinacol rearrangement reaction was involved, and the desired products bearing a quaternary carbon center were efficiently prepared using molecular oxygen (O2) as an ideal oxidant. (Figure presented.).

Dearomatization Strategy for the Synthesis of Arylated 2H-Pyrroles and 2,3,5-Trisubstituted 1H-Pyrroles

The first high-yielding route to arylated 2H-pyrroles was developed. The methodology utilizes 2,5-disubstituted pyrroles that are metalated, and the aryl substituents are introduced by a palladium-catalyzed cross-coupling reaction. The prepared pyrroles can be rearranged to 2,3,5-trisubstituted pyrroles under acidic conditions. Attempts to convert the 2,3,5-trisubstituted pyrroles to 2,3,4,5-tetrasubstituted pyrroles by the dearomatization rearrangement strategy were unsuccessful.

Synthesis of multi-substituted pyrroles using enamides and alkynes catalyzed by Pd(OAc)2 with molecular oxygen as an oxidant

A cyclization reaction between enamides and alkynes catalyzed by palladium(ii) acetate is described. In this method, the molecular oxygen serves as an efficient oxidant for the Pd(ii)/Pd(0) catalytic cycle. The simple reaction conditions permit this methodology to be used as a general tool for the preparation of multi-substituted pyrroles.

Isothiazoles. Part IV. Cycloaddition reactions of diaryl-oxazolones and munchnones to 3-diethylamino-4-(4-methoxyphenyl)-isothiazole 1,1-dioxide: A new synthesis of triarylpyrroles

3-Diethylamino-4-(4-methoxyphenyl)-isothiazole 1,1-dioxide (3) readily reacts with oxazolones 2 and munchnones 7 affording with satisfactory yield 3-diethylamino-4,6-diaryl-3a,4-dihydro-3a-(4-methoxyphenyl)-6aH-pyrrol o[3,4-d]isothiazole 1,1-dioxides 4 an

The Diverse Carbenic and Cationic Chemistry of 3-Diazo-2,5-diphenylpyrrole

3-Diazo-2,5-diphenylpyrrole (1) thermolyzes and photolyzes to 2,5-diphenyl-3H-pyrrolylidene (3), which inserts into methylene hydrogen of cyclohexane and methyne hydrogen of cumene.Hydrogen abstraction to give 2,5-diphenylpyrrole (7) occurs competitively in these systems.Carbene 3 reacts with cyclohexene, allylbenzene, and 2,3-dimethyl-2-butene to give 3-(allylically substituted)-2,5-diphenylpyrroles (15, 20, 21, and 29) as the only products of olefin incorporation along with 7.The initial position of the double bond in the olefin may be altered in the overall insertion process, and cyclopropanes are not isolable.The apparent behavior of 3 with saturated and olefinic hydrocarbons is as singlet 8s and triplet 9t.Reactions of 3 with anisole (31a) and with toluene (31b), benzenes substituted by electron-donor groups, result in selective ortho and/or para substitution to give 2,5-diphenyl-3-(substituted-phenyl)pyrroles (38a, 35, and 38b) and in hydrogen abstraction to 7.Insertion into the methyl groups and hydrogen abstraction also occur in reactions of 3 with 31b, yielding 3-benzyl-2,5-diphenylpyrrole (39) and 1,2-diphenylethane (40).Benzene (42a), however, reacts thermally or photolytically with 1 to form 1,3-diphenyl-2H-cyclooctapyrrole (46a), a member of a new heterocyclic system.Ring expansions to 4-, 5-, and 6-cyano-1,3-diphenyl-2H-cyclooctapyrroles (46b, 46b', and 46b'') and 4-, 5-, and 6-nitro-1,3-diphenyl-2H-cyclooctapyrroles (46c, 46c', and 46c'') are the principal reactions of 3 with benzonitrile (42b) and nitrobenzene (42c). 3-(m-Nitrophenyl)-2,5-diphenylpyrrole (47b) is also formed from 1 and 42c at 170 deg C.Thermolysis and photolysis of 1 to effect substitution and ringexpansion of benzenes may involve electrophilic attack of 8s to form spiropyrrolonorcaradienes (32).Directed heterolytic ring opening of 32 and (1,5 sigmatropic) rearrangements of hydrogen will rationalize the selective ortho and/or para substitution processes.Cyclooctapyrroles may arise from (electrocyclic) isomerization of 32 to spirocycloheptatrienes 44, (1,5 sigmatropic) rearrangement involving ring expansion to 45, and then hydrogen migration.Triplet photosensitization of 1 in 42a and 42b leads to 2,3,5-triphenylpyrrole (47a) and 3-(o-cyanophenyl)-2,5-diphenylpyrrole (47c), products of aromatic substitution rather than ring expansion.Such photolytic processes may involve generation and then addition of 9t to 42a and 42b, spin inversion of the triplet to singlet diradical intermediates, and successive hydrogen migrations.Aniline (59a), N-methylaniline (59b), and N,N-dimethylaniline are nucleophiles in that they are pyrrylated on nitrogen by 1 at 180 deg C.Primary and secondary alcohols and 1 undergo oxidation/reduction to carbonyls and 7; conversion to 3-alkoxy-2,5-diphenylpyrroles is minor except in the presence of ...