37560-45-5

Usage

Aromatic heterocycle

pyrrole

Substituent

3,5-dimethylphenyl group

Attachment

to the nitrogen atom of the pyrrole ring

Use in organic synthesis

as a building block to create compounds with potential pharmacological properties

Unique structure

valuable tool in the development of new drugs and biologically active molecules

Interest in materials science

potential applications in the development of organic electronic devices.

Upstream product

• 109-97-7 pyrrole 
• 22445-41-6 3,5-dimethylphenyl iodide 
• 6117-80-2 1,4-butenediol 
• 99-12-7 5-nitro-m-xylene 
• 110-65-6 1,4-dihydroxybut-2-yne 
• 25653-16-1 tris(3,5-dimethylphenyl) phosphate 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 108-69-0 3,5-dimethylaminoaniline 

Relevant academic research and scientific papers

Utilization of caffeine carbon supported cobalt catalyst in the tandem synthesis of pyrroles from nitroarenes and alkenyl diols

Employing bio-waste caffeine carbon-supported heterogeneous cobalt catalyst, synthesis of various substituted pyrrole derivatives is reported. In this methodology, pyrroles were synthesized through coupling between nitroarenes and alkenyl diols in a tandem manner. Among all the heterogeneous catalysts Co(OAc)2-CC-800 displayed the highest catalytic activity. Preparative scale synthesis of pyrroles and synthesis of anti-tubercular agent 5-(4-(1H-pyrrol-1-yl)phenyl)-1,3,4-oxadiazole-2-thiol revealed the practical applicability of this protocol. Several kinetic experiments and Hammett studies were conducted to understand the probable mechanism and electronic effects on this transformation.

Palladium-catalyzed c(sp2)-n bond cross-coupling with triaryl phosphates

The first general palladium-catalyzed amination of aryl phosphates is described. The combination of MorDalPhos with [Pd(-cinnamyl)Cl]2 enables the amination of electron-rich, electron-neutral, and electron-poor aryl phosphates with a board range of aromatic, aliphatic, and heterocyclic amines. Common functional groups such as ether, keto, ester, and nitrile show an excellent compatibility in this reaction condition. The solvent-free amination reactions are also successful in both solid coupling partners. The gram-scale cross-coupling is achieved by this catalytic system.

Palladium-Catalyzed C(sp2)-N Bond Cross-Coupling with Triaryl Phosphates

The first general palladium-catalyzed amination of aryl phosphates is described. The combination of MorDalPhos with [Pd(?-cinnamyl)Cl]2 enables the amination of electron-rich, electron-neutral, and electron-poor aryl phosphates with a board range of aromatic, aliphatic, and heterocyclic amines. Common functional groups such as ether, keto, ester, and nitrile show an excellent compatibility in this reaction condition. The solvent-free amination reactions are also successful in both solid coupling partners. The gram-scale cross-coupling is achieved by this catalytic system.

MICROCAPSULES AND PROCESSES FOR THEIR PREPARATION

The present invention provides microcapsules encapsulating hydrophilic or hydrophobic active agents in an inorganic shell, processes for their preparation and compositions comprising them.

Efficient and recyclable copper-based MOF-catalyzed N-arylation of N-containing heterocycles with aryliodides

Copper-based MOF-199 was used as an efficient heterogeneous catalyst to catalyze cross-coupling reactions between N-containing heterocycles and aryliodides with high yields. The catalyst can be easily separated from the reaction mixture, and can be reused at least 5 times without significantly decreasing the activity. The XRD results showed that the crystallinity and structure of MOF-199 can be maintained well during the coupling reaction.

Discovery of allosteric and selective inhibitors of inorganic pyrophosphatase from mycobacterium tuberculosis

Inorganic pyrophosphatase (PPiase) is an essential enzyme that hydrolyzes inorganic pyrophosphate (PPi), driving numerous metabolic processes. We report a discovery of an allosteric inhibitor (2,4-bis(aziridin-1-yl)-6-(1-phenylpyrrol-2-yl)-s-triazine) of bacterial PPiases. Analogues of this lead compound were synthesized to target specifically Mycobacterium tuberculosis (Mtb) PPiase (MtPPiase). The best analogue (compound 16) with a Ki of 11 μM for MtPPiase is a species-specific inhibitor. Crystal structures of MtPPiase in complex with the lead compound and one of its analogues (compound 6) demonstrate that the inhibitors bind in a nonconserved interface between monomers of the hexameric MtPPiase in a yet unprecedented pairwise manner, while the remote conserved active site of the enzyme is occupied by a bound PPi substrate. Consistent with the structural studies, the kinetic analysis of the most potent inhibitor has indicated that it functions uncompetitively, by binding to the enzyme-substrate complex. The inhibitors appear to allosterically lock the active site in a closed state causing its dysfunctionalization and blocking the hydrolysis. These inhibitors are the first examples of allosteric, species-selective inhibitors of PPiases, serving as a proof-of-principle that PPiases can be selectively targeted.

Copper-catalysed N-arylation of pyrrole with aryl iodides under ligand-free conditions

A simple, inexpensive and ligand-free copper-catalysed N-arylation of pyrrole with aryl iodides has been developed giving N-arylated products in moderate to excellent yields. The catalyst loading is relative low (5 mol%) and the catalyst system was stable in air.

Octanuclear Cu(I)-dithiophosphates: An efficient catalyst system for N-arylation of azoles, amines, and amides

The formation of a C-N bond via the cross-couplings of aryl iodides with azoles, aryl amine, and amides can be successfully achieved in decent yield by the utilization of both [Cu8(H){S2P(OiPr) 2}6]+ and [Cu8{S2P(OEt) 2}6]2+ as the pre-catalysts.

L-Proline Promoted Ullmann-Type Coupling Reactions of Aryl Iodides with Indoles, Pyrroles, Imidazoles or Pyrazoles

The Ullmann-type coupling reactions of aryl iodides and several nitrogen heterocycles occur at 80-90°C with L-proline as additive, giving N-arylpyrroles, N-arylindoles, N-arylimidazoles, and N-pyrazoles in good to excellent yields.

Copper-catalyzed N-arylation of aryl iodides with benzamides or nitrogen heterocycles in the presence of ethylenediamine

The copper-catalyzed N-arylation of benzamides or nitrogen heterocycles was carried out with catalytic CuI (10 mol%) in the presence of ethylenediamine (10 mol%) as a ligand and K3PO4 or Cs2CO3 as a base under mild conditions.