1426318-72-0

Upstream product

• 1121-60-4 pyridine-2-carbaldehyde 
• 3058-39-7 4-iodobenzonitrile 
• 623-00-7 4-bromobenzenecarbonitrile 
• 98-98-6 2-Picolinic acid 
• 105-07-7 4-cyanobenzaldehyde 
• 109-04-6 2-bromo-pyridine 
• 110-86-1 pyridine 

Downstream Products

• 57954-94-6 4-(pyridin-2-ylcarbonyl)benzonitrile 
• 57954-98-0 2-[(4-cyanophenyl)(hydrazono)methyl]pyridine 
• 57955-00-7 3-(4-cyanophenyl)-[1,2,3]triazolo[1,5-a]pyridine 

Relevant academic research and scientific papers

Design of High-Performance Pyridine/Quinoline Hydrazone Photoswitches

The design of P-type photoswitches with thermal stability of the metastable form of hundreds of years that would efficiently transform using excitation wavelengths above 350 nm remains a challenge in the field of photochromism. In this regard, we designed and synthesized an extended set of 13 pyridine/quinoline hydrazones and systematically investigated the structure-property relationships, defining their kinetic and photoswitching parameters. We show that the operational wavelengths of the pyridine hydrazone structural motif can be effectively shifted toward the visible region without simultaneous loss of their high thermal stability. Furthermore, we characterized the ground-state and excited-state potential energy surfaces with quantum-chemical calculations and ultrafast transient absorption spectroscopy, which allowed us to rationalize both the thermal and photochemical reaction mechanisms of the designed hydrazones. Whereas introducing an electron-withdrawing pyridyl moiety in benzoylpyridine hydrazones leads to thermal stabilities exceeding 200 years, extended π-conjugation in naphthoylquinoline hydrazones pushes the absorption maxima toward the visible spectral region. In either case, the compounds retain highly efficient photoswitching characteristics. Our findings open a route to the rational design of a new family of hydrazone-based P-type photoswitches with high application potential in photonics or photopharmacology.

INHIBITORS OF ANTIGEN PRESENTATION BY HLA-DR

Chromanone compounds, pharmaceutical compositions containing them, methods of making them, and methods of using them including methods for treating disease states, disorders, and conditions associated with the inhibition of antigen presentation by HLA-DR.

Ligand-Free Iridium-Catalyzed Dehydrogenative ortho C?H Borylation of Benzyl-2-Pyridines at Room Temperature

A convenient and ligand-free iridium-catalyzed dehydrogenative ortho C?H borylation of benzyl-2-pyridines has been developed. The reaction proceeds smoothly at room temperature using pinacolborane as a borylating reagent in the presence of catalytic amount of [IrOMe(COD)]2. The reaction is compatible with many functional groups, providing a vast array of ortho borylated products in moderate to excellent yields with excellent selectivities. (Figure presented.).

2-AMINO-BENZIMIDAZOLE DERIVATIVES AND THEIR USE AS 5-LIPOXYGENASE AND/OR PROSTAGLANDIN E SYNTHASE INHIBITORS

The present invention relates to benzimidazole derivatives having the general formula I, wherein n is 0 or 1; X1 and X2 are independently, at each occurrence, CR5 or N; Y is C1-C6 alkylene, wherein alkylene is optionally substituted with one to two C1-C3 alkyl groups; R1 is selected from the group consisting of hydrogen, halogen, C1-C6 alkoxy, -NH2, -NHR6, -NR7R8 and -NH-(R9)n-R10, n being 0 or 1; R2 is selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, -NH2, -NHR6, - NR7R8 and -NH-(R9)n-R10; R3 is selected from the group consisting of hydrogen, hydroxyl, OR11, -NR7R8, C1-C6 alkoxy, C1-C6 alkyl, C3-C10 cycloalkyl, C1-C3 haloalkyl, -C(O)NHR11, aryl, heteroaryl and heterocyclyl, wherein each of said cycloalkyl, aryl, heteroaryl and heterocyclyl is optionally and independently substituted with one to four Ra groups; and R4 is selected from the group consisting of -NH2, -N(R12)(V)pR13, - NH(V)p-OR14, -NHC(O)R15, and groups of formula la shown below, and their use in the treatment of diseases, in particular inflammatory diseases, cancer, stroke and/or Alzheimer's disease.

Facile one-pot synthesis of [1,2,3]triazolo[1,5-a]pyridines from 2-acylpyridines by copper(II)-catalyzed oxidative N-N bond formation

An efficient and simple method for the synthesis of various [1,2,3]triazolo[1,5-a]pyridines has been established. The method involves a copper(II)-catalyzed oxidative N-N bond formation that uses atmospheric oxygen as the terminal oxidant following hydrazonation in one pot. The use of ethyl acetate as the solvent dramatically promotes the oxidative N-N bond-formation reaction and enables the application of oxidative cyclization in the efficient one-pot reaction. A mechanism for the reaction was proposed on the basis of the results of a spectroscopic study. In the same pot: [1,2,3]Triazolo[1,5-a] pyridines are synthesized from the corresponding 2-acylpyridines by a one-pot method, consisting of hydrazonation followed by oxidative cyclization through copper(II)-catalyzed N-N bond formation (see scheme).

Ruthenium catalyzed hydrohydroxyalkylation of isoprene with heteroaromatic secondary alcohols: Isolation and reversible formation of the putative metallacycle intermediate

Heteroaromatic secondary alcohols react with isoprene to form products of hydrohydroxyalkylation in the presence of ruthenium(0) catalysts generated from Ru3(CO)12 and tricyclohexylphosphine, enabling direct conversion of secondary to tertiary alcohols in the absence of premetalated reagents or stoichiometric byproducts. The putative oxaruthenacycle intermediate has been isolated and characterized, and reversible metallacycle formation has been demonstrated.

Metalated N-heterocyclic reagents prepared by the frustrated Lewis pair TMPMgCl·BF3 and their addition to aromatic aldehydes and activated ketones

Treatment of pyridines, quinoline and methylthiopyrazine with the frustrated Lewis pair TMPMgCl·BF3 (1) leads to organotrifluoro borates which react readily with a variety of aromatic aldehydes in the absence of a transition metal catalyst.