144221-02-3

Upstream product

• 16883-69-5 N-phenacylpyridinium bromide 
• 5424-47-5 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride 
• 13196-35-5 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one 
• 1137-94-6 1-(2-phenyl-2-oxoethyl)pyridinium iodide 
• 3437-95-4 2-Iodothiophene 
• 52806-02-7 iodure de 1-methyl-2-phenylpyridinium 
• 1008-89-5 2-phenylpyridine 
• 14593-04-5 3-amino-3-phenyl-1-propanol 
• 115510-91-3 1-(thien-2-yl)ethanol 
• 29526-96-3 1-phenylcyclopropan-1-ol 
• 298229-64-8 1‐(thiophen‐2‐yl)ethanone oxime acetate 
• 98-86-2 acetophenone 
• 110-86-1 pyridine 
• 879-72-1 3-(dimethylamino)propiophenone hydrochloride 

Downstream Products

• 144221-05-6 2-(5-chloro-2-thienyl)-6-phenylpyridine 
• 144221-04-5 5,5'-bis(6-phenyl-2-pyridyl)-2,2'-bithiophene 

Relevant academic research and scientific papers

Phosphine Ligand-Free Ruthenium Complexes as Efficient Catalysts for the Synthesis of Quinolines and Pyridines by Acceptorless Dehydrogenative Coupling Reactions

A series of phosphine-free Ru(III)/Ru(II) complexes of NH functionalized N?N?N pincer ligands exhibit excellent activity for acceptorless dehydrogenative coupling (ADC) of secondary alcohols with 2-aminobenzyl or γ-amino alcohols to quinolines and pyridines. Ru(III) complexes [LRuCl3] (L=6-(3-R1,5-R2-1H-pyrazol-1-yl)-N-(pyridin-2-yl)pyridin-2-amine; 1 a: R1=R2=H (L1); 1 b: R1=R2=Me (L2); 1 c: R1=H, R2=CF3 (L3); 1 d: R1=H, R2=Ph (L4); 1bMe: L=6-(3,5-dimethyl-1H-pyrazol-1-yl)-N-methyl-N-(pyridin-2-yl)pyridin-2-amine (L2Me)) were obtained by refluxing RuCl3 ? xH2O with the corresponding ligand in EtOH. Five Ru(II) complexes [LRu(DMSO-κS)Cl2] (2 a: L=L1; 2 b: L=L2; 2 c: L=L3; 2 d: L=L4; 2bMe: L=L2Me) were formed by reducing the corresponding Ru(III) complex in refluxing EtOH. The latter complexes could also be prepared directly by refluxing Ru(DMSO)4Cl2 with the corresponding ligand in EtOH. These Ru(III) and Ru(II) complexes, especially 1 b/2 b, exhibited high catalytic efficiency and broad functional group tolerance in ADC reactions of secondary alcohols with 2-aminobenzyl or γ-amino alcohols to quinolines and pyridines. A detail mechanistic study indicated the Ru(III) complex was reduced into the Ru(II) species, which is the active catalytic center for ADC via a Ru?H/N?H bifunctional outer-sphere mechanism. This protocol provides a reliable, atom-economical and environmentally benign procedure for C?N and C?C bond formation.

4-HO-TEMPO-Catalyzed Redox Annulation of Cyclopropanols with Oxime Acetates toward Pyridine Derivatives

A 4-HO-TEMPO-catalyzed redox strategy for the synthesis of pyridines through the annulation of cyclopropanols and oxime acetates has been developed. This protocol features good functional group tolerance and high chemoselectivity and also promises to be efficient for the late-stage functionalization of skeletons of drugs and natural products. Mechanism studies indicate that the reaction involves the in situ generated α,β-unsaturated ketones and imines as the key intermediates, which are derived from cyclopropanols and oxime acetates via a TEMPO/TEMPOH redox cycle, respectively. The pyridine products are formed as a result of annulation of enones with imines followed by TEMPO-catalyzed oxidative aromatization by excess oxime acetates. This method not only realizes the TEMPO-catalyzed redox reaction but also broadens the frontiers for TEMPO in catalysis.

C6-Selective Direct Arylation of 2-Phenylpyridine via an Activated N-methylpyridinium Salt: A Combined Experimental and Theoretical Study

An elegant pre-activation strategy, based on the formation of N-methylpyridinium iodide salts for C6-selective direct arylation of 2-phenylpyridines using Pd/Cu cooperative catalysis, has been developed. By this methodology, a wide range of unsymmetrical 2, 6-diarylpyridines were synthesized with high reactivity and regioselectivity as well as good functional group tolerance. In particular, challenging substrates bearing electron donating groups (EDGs), such as OMe, NMe2, were also successfully employed in this reaction. Deuterium incorporation studies revealed that the C?H bond acidity is improved significantly in N-methylpyridinium salts compared with their N-Oxide and N-iminopyridinium ylide counterparts, thus solving the long-standing problem associated with previous strategies for the synthesis of diaryl pyridines. Finally, the control experiments and DFT calculations supported a Pd-catalyzed and Cu-mediated mechanism in which a carbenoid copper species that is formed in-situ from N-methylpyridinium salts, participates in a Pd-catalyzed arylation followed by an iodide-promoted N-demethylation process. (Figure presented.).

Luminescent PtII Complexes of Tridentate Cyclometalating 2,5-Bis(aryl)-pyridine Ligands

Bis-cyclometalated PtII complexes of dianionic 2,5-bis(aryl)-pyridine ligands (L1–6)2–, carrying various cyclometalating or pending aryl groups, are synthesised in two steps. The reactions of H2L protoligands with K2[PtCl4] in acetic acid give the mono-cyclometalated complexes [Pt(HL)Cl]2. Heating these complexes in hot DMSO (dimethyl sulfoxide) yields the double-cyclometalated DMSO complexes [Pt(L1–6)(DMSO)]. The reaction of [Pt(L4)(DMSO)] with N,N-dimethylimidazolium iodide in the presence of KOtBu as the base gives the carbene complex [Pt(L4)(Me2Imd)]. Detailed photophysical studies reveal the intense orange luminescence of these complexes in CH2Cl2 solution, with quantum yields up to 0.22, and increased quantum yields of up to 1.00 in glassy frozen CH2Cl2/MeOH (1:1) and up to 0.44 in PMMA matrices. Detailed electrochemistry (including spectroelectrochemistry) reveals reversible ligand-based first reductions at –2.1 to –2.3 V, irreversible Pt-centred oxidations at around 0.8 V and electrochemical band gaps of 2.8–3.0 eV. Further reduction waves at very negative potentials interfere with the solvent (THF with traces of water) discharge and can be traced, with UV/Vis spectroelectrochemistry, to Pt-centred reductions for the DMSO complexes and to a second ligand-centred reduction for the Me2Imd complex from. The photo/electrochemical properties can be roughly correlated with the ligand pattern and suggest their use in optoelectronic applications.

Synthesis of 2,6-diaryl-substituted pyridines and their antitumor activities

For the development of novel antitumor agents, we designed and synthesized 2,6-diaryl-substituted pyridine derivatives bearing three aryl groups, which are the bioisosteres of terpyridine, and evaluated their biological activities. Most of the 18 prepared compounds showed moderate cytotoxicity against several human cancer cell lines. From the structure-activity relationships we may conclude that the number of aryl groups employed would be critical for their biological activities.

Pyridine ring formation through the photoreaction of arenecarbothioamides with diene-conjugated carbonyl compounds

Irradiation of arenecarbothioamides with hexa-2,4-dienal in benzene solution gives 2-arylpyridines in moderate yields.

Co-ordination Chemistry of 2-Phenyl-6-(2-thienyl)pyridine and 2,6-Bis(2-thienyl)pyridine; New Ambidentate Ligands

The new ligands 2-phenyl-6-(2-thienyl)pyridine (H2pthpy) and 2,6-bis(2-thienyl)pyridine (H2bthpy) exhibit a variety of reactivities with d8 transition-metal complexes.Reaction of H2bthpy with platinum(II) gives complexes in which the ligand adopts Hbthpy-C,N and bthpy-CNC bonding modes, wheras gold(III) converts the ligand into the dimer 5,5'-bis(6-(2-thienyl)-2-pyridyl>-2,2'-bithiophene.Palladium(II) gives mixtures of cyclometallated complexes and dimerised ligand.In contrast, H2pthpy reacts with platinum(II) to give metallated complexes in which the site of metallation is the phenyl rather than the thienyl ring.The reaction of H2pthpy with gold(III) results in clean conversion into the dimer 5,5'-bis(6-phenyl-2-pyridyl)-2,2'-bithiophene and a chlorinated derivative 2-(5-chloro-2-thienyl)-6-phenylpyridine.Once again mixtures of metallated product and ligand reaction products are obtained with palladium(II).