54582-33-1

Upstream product

• 16199-06-7 potassium pyrrolide 
• 75-44-5 phosgene 
• 102-09-0 bis(phenyl) carbonate 
• 109-97-7 pyrrole 
• 530-62-1 1,1'-carbonyldiimidazole 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 497147-39-4 phenyl-di-pyrrol-1-yl-methanol 
• 627546-31-0 1-(1H-pyrrol-1-yl)-2-(triphenylphosphoranylidene)ethanone 
• 736140-81-1 (E)-3-cyclohexyl-1-(1H-pyrrol-1-yl)prop-2-en-1-one 
• 736140-97-9 (2Z)-5-phenyl-1-pyrrol-1-yl-pent-2-en-1-one 
• 736140-79-7 (E)-5-phenyl-1-(1H-pyrrol-1-yl)pent-2-en-1-one 
• 627546-38-7 (2S,3R)-trans-2,3-epoxy-5-phenyl-1-pyrrol-1-yl-pentan-1-one 
• 864953-68-4 ((2S,3R)-3-phenethylaziridin-2-yl)(1H-pyrrol-1-yl)methanone 
• 864953-61-7 (R)-3-methoxyamino-5-phenyl-1-pyrrol-1-yl-pentan-1-one 
• 949013-80-3 3-phenyl-1-pyrrol-1-yl-2-propen-1-one 
• 627546-30-9 (2S,3R)-trans-2,3-epoxy-3-phenyl-1-pyrrol-1-yl-propan-1-one 
• 736140-74-2 (2E)-3-(2-chlorophenyl)-1-pyrrol-1-yl-2-propen-1-one 

Relevant academic research and scientific papers

Aluminum(III)-Catalyzed, Formal Homo-Nazarov-Type Ring-Opening Cyclizations toward the Synthesis of Functionalized Tetrahydroindolizines

A general approach to functionalized 5,6,7,8-tetrahydroindolizines (THIs) is disclosed. The THIs are directly formed from Al(OTf)3-catalyzed, formal homo-Nazarov-type ring-opening cyclizations of N-pyrrolyl cyclopropyl malonamides. The THI products were stable to silica gel chromatography and isolated in up to 97% yield with diastereomeric ratios up to 4.0:1. The cyclization demonstrates good substrate scope as aryl, heteroaryl, gem-dialkyl, heteroatomic, and silylmethyl donor groups on the cyclopropane are tolerated. Moreover, the protocol is both pharmaceutically relevant and environmentally friendly as a cheap, earth-abundant metal catalyst is used along with acetonitrile as a greener solvent.

Conformationally Driven Two- and Three-Photon Cascade Processes in the Stereoselective Photorearrangement of Pyrroles

A TBSO group has been shown to exert a high degree of stereocontrol during the two-photon photocycloaddition/rearrangement of N-butenylpyrroles to complex tricyclic aziridines. Moreover, this and other bulky groups have been shown to change the outcome of the reaction, promoting a new two-photon sequence to tricyclic imines and an unprecedented stereoselective three-photon sequence to azabicyclo[3.3.1]nonanes.

Tetrakis-(N-pyrrolyl)methane: Structurally Important Member of the C(NR2)4 Family

The structural motif C(NR2)4 is rare in chemistry. The formation, NMR spectroscopic characteristics, and X-ray structure are reported for a structurally interesting member of this family, namely tetrakis-(N-pyrrolyl)methane.

Dual emission channels for sensitive discrimination of Cys/Hcy and GSH in plasma and cells

A new selective fluorescent and colorimetric chemosensor for the detection of GSH was developed. The discrimination of GSH from Cys and Hcy is achieved through two emission channel detection. The detection limit of probe 1 for GSH reached 10 nM (3 ppb). The excellent sensitivity and selectivity of probe 1 allow the selective detection of GSH over Cys and Hcy, which can be visualized colorimetrically and/or fluorescently. The sensitive detection of GSH allowed for convenient measurement of the GSH content in human plasma. The presence of GSH in cells was demonstrated through cell imaging.

Carbonic acid diester activation by polymer-bound DBU and its relevance to catalytic N-carbonylation of N-heteroaromatics: Direct evidence for an elusive N-carboxy-substituted amidinium cation intermediate

Polymer-bound DBU (PS-DBU, DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene) is an effective and selective catalyst for solventless N-phenoxycarbonylation of N-heteroaromatics (pyrrole (1), indole (2), and carbazole (3)) with diphenyl carbonate (DPC), used as an

A copper(II)-catalyzed, sequential Michael-aldol reaction for the preparation of 1,2-dihydroquinolines

A copper(II)-catalyzed, sequential Michael addition-aldol condensation reaction of N-carboxybenzyl-protected aminobenzaldehyde with various α,β-unsaturated N-acyl pyrroles is described. Substrate scope was found to include both aryl and aliphatic N-acyl p

Solventless selective phosgene-free N-carbonylation of N-heteroaromatics (pyrrole, indole, carbazole) under mild conditions

N-Heteroaromatics HetNH, such as pyrrole (1), indole (2) and carbazole (3), have been selectively N-carbonylated by a direct reaction with diphenyl carbonate (DPC), used as an environmental friendly carbonyl active species in place of toxic and hazardous phosgene. The carbonylation reaction can be effectively catalyzed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), which can act as a base catalyst by activating the HetNH substrate, and as a nucleophile catalyst by activating the organic carbonate. The influence of reaction parameters (temperature, reaction time, DBU load, DPC/HetNH molar ratio) on the productivity of the process has been also investigated. The synthetic methodology does not require severe temperature conditions, is solventless, simple (only one step), efficient and selective, and offers a new solution to the synthesis of synthetically versatile HetNCO2Ph derivatives through a route alternative to the current traditional phosgenation methods.

α,β-unsaturated N-Acylpyrrole peptidyl derivatives: New proteasome inhibitors

Because of the encouraging results obtained using vinyl ester derivatives, we synthesized and tested a novel series of peptide-based proteasome inhibitors bearing a new pharmacophore unit at the C-terminal. N-Acylpyrrole moiety is a potential substrate for Michael addition by catalytic threonine. Several analogues have demonstrated a selective inhibition of the multicatalytic complex β1 subunits, the capacity to permeate cellular membrane, and good pharmacokinetics properties.

Epi-cinchona based thiourea organocatalyst family as an efficient asymmetric Michael addition promoter: Enantioselective conjugate addition of nitroalkanes to chalcones and α,β-unsaturated N-acylpyrroles

(Chemical Equation Presented) A small set of easily available epi-cinchona based thiourea organocatalysts have been synthesized and tested in enantioselective Michael addition of nitroalkanes to chalcones. These bifunctional catalyst systems promoted the

Superbase-promoted direct N-carbonylation of pyrrole with carbonic acid diesters

Carbonic acid diesters have been investigated as carbonylating agents in the direct reaction with pyrrole (HetNH). In the presence of superbases (DBU, P1-t-Bu, BTPP) as catalysts, the heteroaromatic substrate can be N-carbonylated by direct reaction with carbonic acid diesters under not-severe experimental conditions. The carbonylation reaction makes accessible pyrrole N-carbonyl derivatives (HetNC(O)OR, (HetN)2CO) selectively through a simple straightforward way, which offers a safe eco-friendly alternative to the traditional synthetic methods based on hazardous phosgene or phosgene-derivatives.