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Upstream product

• 108-91-8 cyclohexylamine 
• 873-76-7 para-Chlorobenzyl alcohol 
• 64-18-6 formic acid 
• 637-87-6 1-Chloro-4-iodobenzene 
• 201230-82-2 carbon monoxide 
• 623-03-0 4-Cyanochlorobenzene 
• 108-94-1 cyclohexanone 
• 104-86-9 4-chlorobenzylamine 
• 104-88-1 4-chlorobenzaldehyde 
• 24431-14-9 N-(4-chlorobenzylidene)cyclohexylamine 

Downstream Products

• 1443830-99-6 4-chloro-N-(4-chlorobenzyl)-N-cyclohexyl-6-(4-morpholinyl)-1,3,5-triazin-2-amine 
• 1443830-70-3 4-[(4-chlorobenzyl)(cyclohexyl)amino]-6-(4-morpholinyl)-1,3,5-triazine-2-carbonitrile 
• 24431-14-9 N-(4-chlorobenzylidene)cyclohexylamine 
• 55246-40-7 C₁₄H₁₇Cl₂NO 

Relevant academic research and scientific papers

Trimethyl Borate-Catalyzed, Solvent-Free Reductive Amination

Solvent-free reductive amination of aldehydes and ketones with aliphatic and aromatic amines in high-to-excellent yields has been achieved with sub-stoichiometric trimethyl borate as promoter and ammonia borane as reductant.

Ruthenium(II) complexes of pyridine-carboxamide ligands bearing appended benzothiazole/benzimidazole rings: Structural diversity and catalysis

A series of ruthenium(II) complexes (1–6) of pyridine-carboxamide ligands, HLBT/BI (HLBT = N-(benzo[d]thiazol-2-yl)picolinamide and HLBI = N-(1H-benzo[d]imidazol-2-yl)picolinamide), have been synthesized. All Ru(II) complexes have been characterized by using various spectroscopic techniques (FTIR, UV–Visible, 1H, 13C, 31P NMR and ESI-MS), conductivity and elemental analyses. The solid-state structures of all Ru(II) complexes, except 2, were substantiated by the single crystal X-ray diffraction technique that revealed versatile coordination modes of two bidentate ligands varying between N–N and N–O modes. All Ru(II) complexes exhibited a distorted octahedral geometry with a bidentate ligand while other coordination sites are occupied by either anionic Cl? or neutral co-ligands (CO, PPh3, CH3CN or (CH3)2SO). These well-defined ruthenium(II) complexes have been utilized as the homogeneous catalysts for the alkylation of amines using alcohols ensuing hydrogen borrowing strategy. Out of six complexes, 1 and 2 were found highly effective catalysts towards the N-alkylation of different amines with assorted alcohols. The alkylated products were obtained in excellent yields with good tolerance to a large variety of functional groups. To evaluate the role of putative Ru-hydride species as the intermediate during the catalytic cycle, the respective Ru-H complexes (7 and 8) were synthesized by the reaction of complexes 1 and 2 with NaBH4. Both Ru-H complexes were characterized using different spectroscopic techniques and crystallography. Importantly, both Ru-H complexes, 7 and 8, were directly able to alkylate imine using alcohol thus confirming the involvement of Ru-hydride species as the intermediates during the proposed catalytic cycle.

Design, Synthesis, and Structure-Activity Relationship of Economical Triazole Sulfonamide Aryl Derivatives with High Fungicidal Activity

Plant fungal diseases have caused great decreases in crop quality and yield. As one of the considerable agricultural diseases, cucumber downy mildew (CDM) caused by pseudoperonospora cubensis seriously influences the production of cucumber. Amisulbrom is a commercial agricultural fungicide developed by Nissan Chemical, Ltd., for the control of oomycetes diseases that is highly effective against CDM. However, the synthesis of amisulbrom has a high cost because of the introduction of the bromoindole ring. In addition, the continuous use of amisulbrom might increase the risk of resistance development. Hence, there is an imperative to develop active fungicides with new scaffolds but low cost against CDM. In this study, a series of 1,2,4-triazole-1,3-disulfonamide derivatives were designed, synthesized, and screened. Compound 1j showed a comparable fungicidal activity with amisulbrom, but it was low cost and ecofriendly. It has the potential to be developed as a new fungicide candidate against CDM. Further investigations of structure-activity relationship exhibited the structural requirements of 1,2,4-triazole-1,3-disulfonamide and appropriate modification in N-alkyl benzylamine groups with high fungicidal activity. This research will provide powerful guidance for the design of highly active lead compounds with a novel skeleton and low cost.

Palladium-Catalyzed Solvent-Dependent Divergent Synthesis of Benzylformamides

A palladium-catalyzed carbonylative cascade procedure for the synthesis of benzylformamides from aryl halides has been developed. The properties of the solvent chosen play a decisive role on the selectivity of the outcomes. Non-coordinative solvent facilitates the coordination and insertion of CO to the amino-palladium intermediate which then provides the formamides products. While the use of coordinative solvent leads to the formation of amines. A series of functional groups, including ester, ketone, nitro and cyano, were well tolerated under our conditions. The corresponding benzylformamides products were prepared in moderate to good yields without further optimization. (Figure presented.).

Selective hydrogenation of nitriles to secondary amines catalyzed by a pyridyl-functionalized and alkenyl-tethered NHC-Ru(II) complex

A set of Co(III) and Ru(II) compounds are synthesized bearing pyridyl-functionalized and alkenyl-tethered N-heterocyclic carbene (NHC) ligand (L1). [CoIII(L1)3](PF6)3 (1) was synthesized by the reaction of [L1H]PF6, Co(OAc)2.4H2O, K2CO3 in tetrahydrofuran (THF) under refluxing condition. [RuIIL1(η6-p-cymene)Cl]PF6 (2) was synthesized via transmetallation method. For both compounds, the NHC ligand chelates the metal through carbene carbon and pyridyl nitrogen whereas the butenyl unit remains free. Compound 2 hydrogenates organic nitriles efficiently providing selectively secondary amines. In the presence of external amines, unsymmetrical secondary amines are also obtained.

Synthesis and algicidal activity of new dichlorobenzylamine derivatives against harmful red tides

In the present study, we synthesized 65 dichlorobenzylamine derivatives and investigated their algicidal activity against harmful red tides. The 3,4-dichlorobenzylamine derivatives showed relatively high activity against Cochlodinium polykrikoides, Heterosigma akashiwo, Chattonella marina, and Heterocapsa circularisquama, and the synthesized compounds 27, 28, 33, 34, 35, and 36 showed the highest algicidal activity after 24 h at 0.1 ~ 1.0 μM LC50 against the four harmful algae species. To verify the safety of the compounds, acute ecotoxicology tests using the water flea (Daphnia magna) and zebrafish (Danio rerio) were conducted, and the tests confirmed that compounds 33 and 34 were not harmful because the target organisms showed high survival rates at 15 μM. The results indicate that compounds 33 and 34 are suitable substances for use in controlling harmful algae species.

Bio-inspired transition metal-organic hydride conjugates for catalysis of transfer hydrogenation: Experiment and theory

Taking inspiration from yeast alcohol dehydrogenase (yADH), a benzimidazolium (BI+) organic hydride-acceptor domain has been coupled with a 1,10-phenanthroline (phen) metal-binding domain to afford a novel multifunctional ligand (LBI+/sup

Optimization of Triazine Nitriles as Rhodesain Inhibitors: Structure-Activity Relationships, Bioisosteric Imidazopyridine Nitriles, and X-ray Crystal Structure Analysis with Human CathepsinL

The cysteine protease rhodesain of Trypanosoma brucei parasites causing African sleeping sickness has emerged as a target for the development of new drug candidates. Based on a triazine nitrile moiety as electrophilic headgroup, optimization studies on the substituents for the S1, S2, and S3 pockets of the enzyme were performed using structure-based design and resulted in inhibitors with inhibition constants in the single-digit nanomolar range. Comprehensive structure-activity relationships clarified the binding preferences of the individual pockets of the active site. The S1 pocket tolerates various substituents with a preference for flexible and basic side chains. Variation of the S2 substituent led to high-affinity ligands with inhibition constants down to 2nM for compounds bearing cyclohexyl substituents. Systematic investigations on the S3 pocket revealed its potential to achieve high activities with aromatic vectors that undergo stacking interactions with the planar peptide backbone forming part of the pocket. X-ray crystal structure analysis with the structurally related enzyme human cathepsinL confirmed the binding mode of the triazine ligand series as proposed by molecular modeling. Sub-micromolar inhibition of the proliferation of cultured parasites was achieved for ligands decorated with the best substituents identified through the optimization cycles. In cell-based assays, the introduction of a basic side chain on the inhibitors resulted in a 35-fold increase in antitrypanosomal activity. Finally, bioisosteric imidazopyridine nitriles were studied in order to prevent off-target effects with unselective nucleophiles by decreasing the inherent electrophilicity of the triazine nitrile headgroup. Using this ligand, the stabilization by intramolecular hydrogen bonding of the thioimidate intermediate, formed upon attack of the catalytic cysteine residue, compensates for the lower reactivity of the headgroup. The imidazopyridine nitrile ligand showed excellent stability toward the thiol nucleophile glutathione in a quantitative invitro assay and fourfold lower cytotoxicity than the parent triazine nitrile.

Bio-inspired catalytic imine reduction by rhodium complexes with tethered hantzsch pyridinium groups: Evidence for direct hydride transfer from dihydropyridine to metal-activated substrate

Inspired by Nature: A conceptually new design for a catalyst, combining a metal center abutted to an organic hydride donor, is demonstrated for the formate-driven transfer hydrogenation of imines under ambient conditions. A key step, transfer of hydride from the organohydride donor to the metal-polarized substrate, mirrors that in metallo-(de)hydrogenase enzymes.