50966-74-0

Usage

Uses

Used in Coordination Chemistry:
2-(1H-Pyrrol-1-yl)pyridine is used as a bidentate ligand for [forming coordination complexes with metal ions] because of its ability to chelate with metal ions, enhancing the stability and properties of the resulting complexes.
Used in Chemical Synthesis:
2-(1H-Pyrrol-1-yl)pyridine is used as a building block or intermediate for [synthesis of more complex organic compounds] due to its reactive nature and the presence of nitrogen atoms that can participate in various chemical reactions.
Used in Pharmaceutical Industry:
2-(1H-Pyrrol-1-yl)pyridine is used as a molecular scaffold for [designing new pharmaceutical compounds] because of its potential to be incorporated into drug molecules, contributing to their biological activity and selectivity.
Used in Material Science:
2-(1H-Pyrrol-1-yl)pyridine is used as a component in the development of [novel materials with specific properties] such as organic semiconductors or sensors, owing to its electronic and structural characteristics.

InChI:InChI=1/C9H8N2/c1-2-6-10-9(5-1)11-7-3-4-8-11/h1-8H

Upstream product

• 109-09-1 2-chloropyridine 
• 16199-06-7 potassium pyrrolide 
• 109-97-7 pyrrole 
• 5029-67-4 2-iodopyridine 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 504-29-0 2-aminopyridine 
• 526-99-8 meso-galactaric acid 
• 109-04-6 2-bromo-pyridine 

Relevant academic research and scientific papers

CYCLOMETALLATION OF A PYRROLE RING OF 2-(1-PYRROLYL)PYRIDINE WITH PALLADIUM(II) AND RHODIUM(III)

2-(1-Pyrrolyl)pyridine (Hplp) is cyclometallated with lithium tetrachloropalladate(II) and hexahalogenotetrakis(tri-n-butylphosphine)dirhodium(III) to give 2 and (X=Cl, Br; PBu3=tri-n-butylphosphine), respectively, where deprotonated plp is coordinated via the pyridine-N and pyrrole-2C atoms forming a five-membered metallacycle. 2 reacts with pyridine (py) and with PBu3 to form the adducts (L=py, PBu3) and with acetylacetone (Hacac) to afford the complex .Metathesis of with excess lithium iodide gives a mixed halogeno complex .These complexes are characterized spectroscopically.

Ruthenium-Catalyzed, Site-Selective C-H Allylation of Indoles with Allyl Alcohols as Coupling Partners

A new ruthenium-catalyzed, heteroatom-directed strategy for C-H allylation of indoles is described. The use of allyl alcohols as coupling partners as well as pyridine as the removable directing group is highlighted. This methodology provides access to C2-allylated indoles by utilizing a strategy that does not require prefunctionalization of either of the coupling partners.

Ultrasound-assisted bismuth nitrate-induced green synthesis of novel pyrrole derivatives and their biological evaluation as anticancer agents

A series of novel N-substituted pyrrole derivatives have been designed and synthesized following ultrasound-assisted and bismuth nitrate-catalyzed eco-friendly route. This reaction has also provided a general method to prepare diverse varieties of N-substituted pyrroles with less nucleophilic polyaromatic amines. Based on 1H NMR spectroscopy, a plausible mechanistic pathway has been advanced. Cytotoxicity of some selected N-substituted pyrrole derivatives has been evaluated in vitro in a panel of mammalian cancer cell lines which includes liver cancer cell lines (HepG2 and Hepa1-6), colon cancer cell lines (HT-29 and Caco-2), a cervical cancer cell line (HeLa) and NIH3T3 cells. Two compounds, 5-(1H-pyrrol-1-yl)-1,10-phenanthroline (9) and 1-(phenanthren-2-yl)-1H-pyrrole (10) have shown good cytotoxicity against some cancer cell lines. Furthermore, these compounds have exhibited cytotoxic specificity against liver cancer cell lines in vitro when compared with normal cultured primary hepatocytes.

Buchwald-Hartwig Amination of Coordinating Heterocycles Enabled by Large-but-Flexible Pd-BIAN-NHC Catalysts**

A new class of large-but-flexible Pd-BIAN-NHC catalysts (BIAN=acenaphthoimidazolylidene, NHC=N-heterocyclic carbene) has been rationally designed to enable the challenging Buchwald-Hartwig amination of coordinating heterocycles. This robust class of BIAN-NHC catalysts permits cross-coupling under practical aerobic conditions of a variety of heterocycles with aryl, alkyl, and heteroarylamines, including historically challenging oxazoles and thiazoles as well as electron-deficient heterocycles containing multiple heteroatoms with BIAN-INon (N,N′-bis(2,6-di(4-heptyl)phenyl)-7H-acenaphtho[1,2-d]imidazol-8-ylidene) as the most effective ligand. Studies on the ligand structure and electronic properties of the carbene center are reported. The study should facilitate the discovery of even more active catalyst systems based on the unique BIAN-NHC scaffold.

Cobalt-Catalyzed Enantioselective Hydroarylation of 1,6-Enynes

An asymmetric hydroarylative cyclization of enynes involving a C-H bond cleavage is reported. The cobalt-catalyzed cascade generates three new bonds in an atom-economical fashion. The products were obtained in excellent yields and excellent enantioselectivities as single diastereo- and regioisomers. Preliminary mechanistic studies indicate that the reaction shows no intermolecular C-H crossover. This work highlights the potential of cobalt catalysis in C-H bond functionalization and enantioselective domino reactivity.

Methyl-α-d-glucopyranoside as Green Ligand for Selective Copper-Catalyzed N-Arylation

In the selective N-arylation of amines or azoles with aryl halidesa-, methyl-α-d-glucopyranoside (MG) was found to function as a green ligand of copper powder. In addition, nitrogen heterocyclic amine compounds can also undergo the N-arylation coupling with heterocyclic aryl chlorides. This process allows access to a variety of aromatic amines and aryl azoles under mild reaction conditions, has good tolerance, and proceeds in moderate to high yield.

Cu(II)-catalyzed C-N coupling of (hetero)aryl halides and N-Nucleophiles promoted by α-benzoin oxime

We first reported the new application of a translate metal chelating ligand α-benzoin oxime for improving Cu-catalyzed C-N coupling reactions. The system could catalyse coupling reactions of (hetero)aryl halides with a wide of nucleophiles (e.g., azoles, piperidine, pyrrolidine and amino acids) in moderate to excellent yields. The protocol allows rapid access to the most common scaαolds found in FDA-approved pharmaceuticals.

Activation Relay on Rhodium-Catalyzed C-H Aminomethylation in Cooperation with Photoredox Catalysis

A site selective C-H aminomethylation at indole's C3 position has been achieved by merging rhodium(III)-catalyzed C-H activation and photoredox catalysis in a one-pot manner. An investigation of the mechanistic insights rationalized the essence of the activation relay and the combination mode.

Nitroarenes as the Nitrogen Source in Intermolecular Palladium-Catalyzed Aryl C–H Bond Aminocarbonylation Reactions

A three-component palladium-catalyzed aminocarbonylation of aryl and heteroaryl sp2 C?H bonds using nitroarenes as the nitrogen source was achieved using Mo(CO)6 as the reductant and origin of the CO. This intermolecular C?H bond functionalization does not requires any exogenous ligand to be added, and our mechanism experiments indicate that the palladacycle catalyst serves two roles in the aminocarbonylation reaction: reduce the nitroarene to a nitrosoarene and activate the sp2 C?H bond.

A triazine-phosphite polymeric ligand bearing cage-like P,N-ligation sites: An efficient ligand in the nickel-catalyzed amination of aryl chlorides and phenols

A novel P,N-ligand was introduced for efficient Ni-catalyzed amination of aryl chlorides. Reaction of cyanuric acid (1,3,5-triazine-2,4,6-triol) and trichlorophosphine (PCl3) resulted in the production of a new porous material (TPPM) containing triazine rings with phosphite moieties in a sheet morphology. Cavities in the prepared compound create sites on the surface of the material with appropriate ligation character to coordinate with metals for catalytic purposes. The nickel-catalyzed amination of aryl chlorides and of phenols in their 2,4,6-triaryloxy-1,3,5-triazine (TAT) protected form were efficiently accomplished in the presence of this easily prepared and reusable P,N-ligand under mild reaction conditions. More importantly, TPPM was reusable for 5 iterations following this protocol without significantly decreasing in its activity.