23694-49-7

Upstream product

• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 2393-23-9 4-methoxy-benzylamine 
• 109-96-6 3-Pyrroline 
• 123-11-5 4-methoxy-benzaldehyde 
• 618-28-0 trans-4-hydroxy-D,L-proline 
• 122439-15-0 N-(4-methoxybenzyl)pyrrolidine 
• 51-35-4 4R-4-hydroxyproline 
• 623-12-1 4-chloromethoxybenzene 
• 2746-25-0 p-Methoxybenzyl bromide 
• 110-65-6 1,4-dihydroxybut-2-yne 
• 821-11-4 trans-butene-1,4-diol 
• 6117-80-2 1,4-butenediol 
• 110-63-4 Butane-1,4-diol 
• 109-97-7 pyrrole 

Downstream Products

• 1256844-80-0 (1-(4-methoxybenzyl)-1H-pyrrol-2-yl)(phenyl)methanone 
• 1476783-13-7 C₂₅H₂₆N₂O₂ 
• 199986-93-1 1-(4-methoxybenzyl)-2,5-diphenyl-pyrrole 

Relevant academic research and scientific papers

An enantioselective synthesis of α-alkylated pyrroles: Via cooperative isothiourea/palladium catalysis

Herein we describe the direct enantioselective Lewis base/Pd catalysed α-allylation of pyrrole acetic acid esters. This provides high isolated yields of highly enantioenriched products and exhibits broad reaction scope with respect to both reaction partners. The products can be readily elaborated in a manner which points towards potential applications in target directed synthesis.

Sustainable Manganese-Catalyzed Solvent-Free Synthesis of Pyrroles from 1,4-Diols and Primary Amines

A general and selective metal-catalyzed conversion of biomass-derived primary diols and amines to the highly valuable 2,5-unsubstituted pyrroles has been developed. The reaction is catalyzed by a stable nonprecious manganese complex (1 mol %) in the absence of organic solvents whereby water and molecular hydrogen are the only side products. The manganese catalyst shows unprecedented selectivity, avoiding the formation of pyrrolidines, cyclic imides, and lactones.

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.

Iron-catalyzed sustainable synthesis of pyrrole

Efficient, sustainable, highly regiospecific substituted pyrroles were synthesized using a well-defined, air stable, molecular iron(0) complex. The developed methodology is broadly applicable and tolerates a variety of functional groups. C-2, C-3, and C-2 & C-4 substituted pyrroles were synthesized in good yield. Symmetrical bis-pyrroles were accessible for the first time using an iron catalyst. On the basis of the experimental observation, we propose that the reaction proceeds through a hydrogen autotransfer process followed by second oxidation/ intramolecular dehydrative condensation to provide the pyrrole.

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.

Suzuki-miyaura cross-coupling of potassium trifluoro(N -methylheteroaryl) borates with aryl and heteroaryl halides

The synthesis of potassium trifluoro(N-methylheteroaryl)borates and their use in cross-coupling reactions with various aryl and heteroaryl halides to construct N-methyl heteroaryl-substituted aromatic and heteroaromatic compounds are reported.

A new facile approach to N-alkylpyrroles from direct redox reaction of 4-hydroxy-l-proline with aldehydes

An unprecedented acetic acid-catalyzed efficient access to N-alkylpyrroles from reaction of 4-hydroxy-l-proline with a variety of aldehydes has been achieved in good to excellent yields under mild reaction conditions.

Decarboxylative formation of N-alkyl pyrroles from 4-hydroxyproline

N-Alkyl pyrroles are obtained in a single step from 4-hydroxyproline and aldehydes in just 15 min under microwave irradiation.

O-Iodoxybenzoic acid (IBX): A versatile reagent for the synthesis of N-substituted pyrroles mediated by β-cyclodextrin in water

O-Iodoxybenzoic acid (IBX), a very mild and efficient hypervalent iodine(V) reagent, aromatizes diversely substituted 1-benzylpyrrolidines and N-substituted l-proline analogues to the corresponding substituted pyrroles in good to excellent yields under mild conditions mediated by β-cyclodextrin in water at room temperature. To the best of our knowledge, this is the first report on IBX, promoting complete aromatization leading to N-benzylpyrroles from the corresponding saturated five membered heterocyclic derivatives in water medium.

Friedel - Crafts acylation of pyrroles and indoles using 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) as a nucleophilic catalyst

1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) has been shown to be an effective catalyst for the regioselective Friedel - Crafts C-acylation of pyrroles and indoles in high yields. A detailed mechanistic study implies that DBN is acting as a nucleophilic organocatalyst, with the X-ray crystal structure of a key N-acyl-amidine intermediate having been determined for the first time.