83306-64-3

Upstream product

• 95-49-8 2-methylchlorobenzene 
• 104-94-9 4-methoxy-aniline 
• 89-97-4 2-CHLOROBENZYLAMINE 
• 2101-87-3 p-methoxy-phenylazide 
• 2039-87-4 2-chlorostyrene 
• 100-17-4 para-methoxynitrobenzene 
• 17849-38-6 2-Chlorobenzyl alcohol 
• 127428-62-0 2-amino-2-(2-chlorophenyl)ethan-1-ol 
• 89-98-5 2-chloro-benzaldehyde 
• 86169-24-6 2-amino-(2-chlorophenyl)ethanoic acid 

Downstream Products

• 85450-34-6 (2-{[(E)-4-Methoxy-phenylimino]-methyl}-phenyl)-triphenyl-phosphonium; chloride 
• 76553-73-6 [1-(2-Chloro-phenyl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine; compound with trichloro-acetic acid 
• 1061672-34-1 (2E,5R)-5-(4-methoxyphenylamino)-5-(2-chlorophenyl)-1-(piperidin-1-yl)pent-2-en-1-one 
• 1133378-57-0 (2S,3S)-2-(2-chlorophenyl)-1-(4-methoxyphenyl)-1,2,3,4-tetrahydropyridine-3-carbaldehyde 
• 1203-68-5 2-Phenylbenzaldehyde 
• 100-52-7 benzaldehyde 
• 169618-84-2 [1,1’:3’,1’’-terphenyl]-2’-carbaldehyde 
• 176697-97-5 2-(2-chlorophenyl)-1-(4-methoxyphenyl)-2,3-dihydropyridin-4(1H)-one 
• 1374021-12-1 (S)-2-(2-chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one 

Relevant academic research and scientific papers

Iron-Catalyzed Hydrogen Transfer Reduction of Nitroarenes with Alcohols: Synthesis of Imines and Aza Heterocycles

A straightforward and selective reduction of nitroarenes with various alcohols was efficiently developed using an iron catalyst via a hydrogen transfer methodology. This protocol led specifically to imines in 30-91% yields, with a good functional group tolerance. Noticeably, starting from o-nitroaniline derivatives, in the presence of alcohols, benzimidazoles can be obtained in 64-72% yields when the reaction was performed with an additional oxidant, DDQ, and quinoxalines were prepared from 1,2-diols in 28-96% yields. This methodology, unprecedented at iron for imines, also provides a sustainable alternative for the preparation of quinoxalines and benzimidazoles.

Non-Bonding Electron Pair versus π-Electrons in Solution Phase Halogen Bond Catalysis: Povarov Reaction of 2-Vinylindoles and Imines

The non-bonding electron pair (n-pair) of heteroatoms and π-electrons are both efficient halogen bond (XB) acceptors. In solid and gas phase studies, n-pairs generally prevail over π-bonding orbitals as XB acceptors, whereas few studies have been conducte

Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C=C Bond Cleavage

C=C bond breaking to access the C=N bond remains an underdeveloped area. A new protocol for C=C bond cleavage of alkenes under nonoxidative conditions to produce imines via an iron-catalyzed nitrene transfer reaction of 4-hydroxystilbenes with aryl azides is reported. The success of various sequential one-pot reactions reveals that the good compatibility of this method makes it very attractive for synthetic applications. On the basis of experimental observations, a plausible reaction mechanism is also proposed.

Unsymmetrical indazolyl-pyridinyl-triazole ligand-promoted highly active iridium complexes supported on hydrotalcite and its catalytic application in water

Herein, an indazolyl-pyridinyl-triazole ligand was synthesized and its iridium complex supported on hydrotalcite was characterized via X-ray power diffraction (XRD), X-ray photoelectron spectroscopy (XPS), energy dispersive X-ray (EDX) spectroscopy and transmission electron microscopy (TEM). This new heterogeneous catalyst bearing the unsymmetrical indazolyl-pyridinyl-triazole ligand exhibits high catalytic activity in water. Both functionalized amines and imines were obtained from the challenging selective reaction of benzylamines with arylamines through transfer hydrogenation and dehydrogenation under clean conditions. In particular, it was observed that this catalyst system showed good recovery performance in water. Mechanistic studies showed that this transformation occurs via amine dehydrogenation, hydrolysis and condensation processes. The direct capture of the reaction intermediate provides sufficient proof for this process.

Synthesis and biological evaluation of new fluconazole β-lactam conjugates linked via 1,2,3-triazole

Novel 1,2,3-triazole-linked β-lactam-fluconazole conjugates 12(a-l) were designed and synthesized. The compounds showed potent antifungal activity against two pathogenic Candida strains; Candida albicans ATCC 24433 and Candida albicans ATCC 10231 with MIC values in the range of 0.0625-2 μg mL-1. Compounds 12h, 12j and 12k showed promising antifungal activity against all the tested fungal pathogens except C. neoformans ATCC 34554 compared to fluconazole. Compound 12j in which the β-lactam ring was formed using para-anisidine and benzaldehyde was found to be more potent than fluconazole against all the fungal strains with an IC50 value of -1 for Candida albicans (ATCC 24433). Mechanistic studies for active compounds revealed that the antifungal action was due to ergosterol inhibition. Compounds 12h and 12j at a concentration of 0.125 μg mL-1 caused 91.5 and 96.8% ergosterol depletion, respectively, compared to fluconazole which at the same concentration caused 49% ergosterol depletion. The molecular docking study revealed that all the fluconazole β-lactam conjugates 12(a-l) could snugly fit into the active site of lanosterol 14α-demethylase (CYP51) with varying degrees of affinities. As anticipated, the binding energy for compound 12j (-58.961 kcal mol-1) was much smaller than that for fluconazole (-52.92 kcal mol-1). The synthesized compounds have therapeutic potential for the control of candidemia.

Paclitaxel Biosynthesis: Adenylation and Thiolation Domains of an NRPS TycA PheAT Module Produce Various Arylisoserine CoA Thioesters

Structure-activity relationship studies show that the phenylisoserinyl moiety of paclitaxel (Taxol) is largely necessary for the effective anticancer activity. Several paclitaxel analogues with a variant isoserinyl side chain have improved pharmaceutical

Quinone-catalyzed oxidative deformylation: Synthesis of imines from amino alcohols

A new method for imine synthesis by way of quinone-catalyzed oxidative deformylation of 1, 2-amino alcohols is reported. A wide range of readily accessible amino alcohols and primary amines can be reacted to provide N-protected imine products. The methodology presented provides a novel organocatalytic approach for imine synthesis and demonstrates the synthetic versatility of quinone-catalyzed oxidative C-C bond cleavage.

Homologation of α-aryl amino acids through quinone-catalyzed decarboxylation/Mukaiyama-Mannich addition

A new method for amino acid homologation by way of formal C-C bond functionalization is reported. This method utilizes a 2-step/1-pot protocol to convert α-amino acids to their corresponding N-protected β-amino esters through quinone-catalyzed oxidative decarboxylation/in situ Mukaiyama-Mannich addition. The scope and limitations of this chemistry are presented. This methodology provides an alternative to the classical Arndt-Eistert homologation for accessing β-amino acid derivatives. The resulting N-protected amine products can be easily deprotected to afford the corresponding free amines.

Enantioselective synthesis of 1,2,5,6-tetrahydropyridines (THPs): Via proline-catalyzed direct Mannich-cyclization/domino oxidation-reduction sequence: Application for medicinally important N-heterocycles

An enantioselective multi-component synthesis of 1,2,5,6-tetrahydropyridines (THPs) has been developed through a one-pot domino-process. This transformation proceeds through proline-catalyzed direct Mannich reaction-cyclization of glutaraldehyde with in s

Ir-Catalyzed C?H Amidation of Aldehydes with Stoichiometric/Catalytic Directing Group

Ir-catalyzed sp2C?H amidation of aldehydes with various anilines as stoichiometric or catalytic directing groups was accomplished. A wide range of substrates were selectively amidated in good to excellent yields with broad functional group tolerance. The iridacycle complexes were isolated, characterized, and proved as key intermediates. Kinetic studies and Hammett plots provided detailed understandings of this amidation. According to the mechanism, the electron-rich ArSO2N3was proved effective for intermolecular sp3C?H amidation.