43191-23-7

Upstream product

• 1193779-39-3 diethyl [5-methyl-2-(phenylamino)pyridin-3-yl]phosphonate 
• 109-04-6 2-bromo-pyridine 
• 1603-41-4 (5-methyl-pyridin-2-yl)amine 
• 98-80-6 phenylboronic acid 
• 591-50-4 iodobenzene 
• 17282-00-7 3-bromo-5-methylpyridin-2-amine 
• 108-86-1 bromobenzene 
• 3510-66-5 2-Bromo-5-methylpyridine 
• 62-53-3 aniline 
• 1003-73-2 3-picoline-N-oxide 
• 59346-37-1 (3aS,7aS)-6-Methyl-3-phenyl-3a,7a-dihydro-3H-oxazolo[4,5-b]pyridin-2-one 
• 103-71-9 phenyl isocyanate 

Downstream Products

• 1570075-54-5 N-([1,1'-biphenyl]-2-yl)-5-methylpyridin-2-amine 
• 1383232-41-4 N-methyl-N-phenyl-2-amino-5-methylpyridine 
• 88474-34-4 2-methylbenzo[4,5]imidazo[1,2-a]pyridine 
• 81416-34-4 5-methyl-1-phenylcarbamoyl-2-phenylimino-1,2-dihydropyridine 
• 99758-04-0 5-methyl-2-(N-phenylcarbamoylanilino)pyridine 

Relevant academic research and scientific papers

Rapid access to diverse α-carbolines through sequential transition metal catalyzed amination and direct C-H arylation

An efficient sequence of Pd catalyzed amination and direct C-H arylation for a synthesis of pharmacologically important α-carbolines is described. The outstanding feature in the synthetic sequence is that a combination of DBU and 2-(dicyclohexylphosphino)

Tunable Electrochemical C?N versus N?N Bond Formation of Nitrogen-Centered Radicals Enabled by Dehydrogenative Dearomatization: Biological Applications

Herein, an environmentally friendly electrochemical approach is reported that takes advantage of the captodative effect and delocalization effect to generate nitrogen-centered radicals (NCRs). By changing the reaction parameters of the electrode material and feedstock solubility, dearomatization enabled a selective dehydrogenative C?N versus N?N bond formation reaction. Hence, pyrido[1,2-a]benzimidazole and tetraarylhydrazine frameworks were prepared through a sustainable transition-metal- and exogenous oxidant-free strategy with broad generality. Bioactivity assays demonstrated that pyrido[1,2-a]benzimidazoles displayed antimicrobial activity and cytotoxicity against human cancer cells. Compound 21 exhibited good photochemical properties with a large Stokes shift (approximately 130 nm) and was successfully applied to subcellular imaging. A preliminary mechanism investigation and density functional theory (DFT) calculations revealed the possible reaction pathway.

PROSTACYCLIN RECEPTOR AGONIST

A compound represented by formula (I) or an isomer or a pharmaceutically acceptable salt thereof. The present invention also relates to an application of the same in preparing a drug for treating a disease related to a PGI2 receptor.

Iridium(III)-Catalyzed Tandem Annulation of Pyridine-Substituted Anilines and α-Cl Ketones for Obtaining 2-Arylindoles

A facile and expeditious protocol for the synthesis of 2-arylindole compounds from readily available N-(2-pyridyl)anilines and commercially available α-Cl ketones through iridium-catalyzed C-H activation and cyclization is reported here. As a complementary approach to the conventional strategies for indole synthesis, the transformation exhibits powerful reactivity, tolerates a large number of functional groups, and proceeds with good to excellent yields under mild conditions, providing a straightforward method to obtain structurally diverse and valuable indole scaffolds. Furthermore, the reaction could be easily scaled up to gram scale.

Ruthenium-catalyzed synthesis of indole derivatives from: N -aryl-2-aminopyridines and alpha-carbonyl sulfoxonium ylides

Indole is a ubiquitous structural motif with important applications in many areas of chemistry. Given this, a simple and efficient Ru(ii)-catalyzed synthesis of indole via intermolecular annulation of N-aryl-2-aminopyridines and sulfoxonium ylides was proposed and accomplished. Excellent selectivity and good functional group tolerance of this transformation were observed. This protocol provides easy access to a wide variety of useful indoles in the presence of a commercially available [Ru(p-cymene)Cl2]2 catalyst. A possible mechanism for the reaction pathway was also proposed. More importantly, this reaction will offer a useful method for the construction of enantioenriched indole frameworks.

Ligand free copper-catalyzed N-arylation of heteroarylamines

An efficient protocol for ligand-free Cu-catalyzed N-arylation of heteroarylamines has been developed. With the use of 1% CuI, a wide range of aryl iodides and bromides coupled with heteroarylamines to afford the corresponding products in high yields. Further, this protocol is particularly suitable for reactions of the most hindered aryl iodides with 2-aminopyridines.

Palladium(II)-catalyzed direct ortho arylation of 4-methyl-N-phenylpyridin- 2-amines via C-H activation/C-C coupling and synthetic applications

The direct ortho arylation of 4-methyl-N-phenylpyridin-2-amines via palladium(II)-catalyzed C-H activation is described. Treatment of 4-methyl-N-phenylpyridin-2-amine with potassium aryltrifluoroborate using 10 mol % of palladium(II) acetate as the catalyst, 2 equiv of copper(II) acetate as the oxidant, and 1 equiv of p-benzoquinone in tert-butyl alcohol gave ortho-arylated products in modest to excellent yields. This reaction shows good functional group compatibility. A series of 1H NMR titration experiments and controlled experiments elucidating the reaction mechanism were carried out. The key intermediate, 4-methyl-N-phenylpyridin-2-amine palladacycle, was isolated and characterized by X-ray crystallography. The advanced transformations of ortho-phenylated 4-methyl-N-phenylpyridin-2-amine to N-(4-methylpyridin-2-yl)-9H-carbazole, biphenyl-2-amine, and 3-methyl-6-phenylpyrido[1,2-a]benzimidazole were successfully demonstrated as potential synthetic applications.

Palladium-catalyzed oxidative alkynylation of arene C-H bond using the chelation-assisted strategy

Palladium-catalyzed alkynylation of arene C-H bonds with (triisopropylsilyl)acetylene was developed for the first time under oxidative conditions in the present study. Among various type of directing groups examined, the N-phenyl-2-aminopyridine skeleton was shown to be most effective and selective for the Pd-catalyzed direct alkynylation reaction, and the desired alkynylated products were obtained in moderate to good yields.

Pyrido-annulated 1,3-azaphospholes: Synthesis of 1,3-azaphospholo[5,4-b] pyridines and preliminary reactivity studies

Pyrido-annulated σ2-phosphorus heterocycles, 1,3-azaphospholo[5,4-b]pyridines 4 and 5, were synthesized by reduction of diethyl 2-aminopyridme-3-phosphonates 1 with LiAlH4 and cyclocondensation of the resulting 2-amino-3-phosphanylpyridines 2 with dimethylformamide and dimethylacetamide dimethyl acetal, respectively, via intermediate phosphaalkenes 3. The P=C-N heterocycles are stable in the presence of OH and NH compounds but add tBuLi at the P=C bond. Reaction with one equivalent of M(CO)5(thf) leads to η1-P-coordinated (azaphospholo[5,4-b]pyridine)M(CO)5 complexes (M = Cr, Mo, W). Spectroscopic data are in accordance with the dominance of π-acceptor properties. X-ray crystal structure analyses reveal "base-pairing" of 2-amino3-phosphanylpyridine (2a) and NH-functional azaphospholopyridine 5a by N-H...N hydrogen bonds, and the competing formation of 1,3-diphosphetane 6c from the phosphaalkene intermediate.

A direct intramolecular C-H amination reaction cocatalyzed by copper(II) and iron(III) as part of an efficient route for the synthesis of pyrido[1,2-a ]benzimidazoles from N-aryl-2-aminopyridines

A novel and efficient synthesis of pyrido[1,2-a]benzimidazoles through direct intramolecular aromatic C-H amination of N-aryl-2-aminopyridines has been developed. The reaction, cocatalyzed by Cu(OAc)2 and Fe(NO 3)3?9H