A Fluoroponytailed NHC-Silver Complex Formed from Vinylimidazolium/AgNO3 under Aqueous-Ammoniacal Conditions.

3-(1H,1H,2H,2H-Perfluorooctyl)-1-vinylimidazolium chloride [2126844-17-3], a strong fluorosurfactant with remarkably high solubility in water, was expediently converted into the respective doubly NHC-complexed silver salt with nitrate as counter ion in quantitative yield. Due to its vinyl substituents, [bis(3-(1H,1H,2H,2H-perfluorooctyl)-1-vinylimidazol-2-ylidene)silver(I)] nitrate, Ag(FNHC)2NO3, represents a polymerizable N-heterocyclic carbene transfer reagent, thus potentially offering simple and robust access to coordination polymers with crosslinking metal bridges. The compound was characterized by infrared and NMR spectroscopy, mass spectrometry as well as elemental analysis, and supplemented by X-ray single-crystal structure determination. It crystallizes in the monoclinic crystal system in the space group P21/c. With 173.3°, the geometry of the Ag-carbene bridge deviates slightly from linearity. The disordered perfluoroalkyl side chains exhibit a helical conformation.

Bacterial Catabolism of Biphenyls: Synthesis and Evaluation of Analogues.

A series of alkylated 2,3-dihydroxybiphenyls has been prepared on the gram scale by using an effective Directed ortho Metalation-Suzuki-Miyaura cross-coupling strategy. These compounds have been used to investigate the substrate specificity of the meta-cleavage dioxygenase BphC, a key enzyme in the microbial catabolism of biphenyl. Isolation and characterization of the meta-cleavage products will allow further study of related processes, including the catabolism of lignin-derived biphenyls.

A short synthesis of Dronedarone.

A modification of the Nenitzescu reaction was used to obtain Dronedarone from quinonimine 20 and 1,3-diketone 14 (R = CH2CH2CH2NBu2) in a two-stage process in almost 55% overall yield. Our results represent significant improvement over other state-of-the-art methods as no extra steps for the decoration of the benzofuran core are required.

Synthesis of enantiopure antiobesity drug lorcaserin.

Acylation of enantiomerically pure (R)-2-(3-chlorophenyl)propan-1-amine using chloroacetyl chloride, followed by borane reduction and aluminum chloride catalyzed cyclization yielded enantiopure lorcaserin.

Biphenyl sulfonic acid ligands for catalytic C-N cross coupling of aryl halides with anilines and secondary amines.

The use of two biphenyl sulfonic acid ligands for the catalytic C-N cross coupling of aryl halides with anilines, 3-aminopyridine, and secondary amines is reported. Our results represent a significant improvement compared to state of the art methods especially with regards to the removal of palladium.

Iclaprim mesylate displaying a hydrogen-bonded mol-ecular tape.

The title compound, 2,6-di-amino-5-[(2-cyclo-propyl-7,8-dimeth-oxy-2H-1-benzo-pyran-5-yl)meth-yl]pyrimidin-1-ium methane-sulfonate, C19H23N4O3 +·CH3O3S-, is a salt made up from a protonated iclaprim mol-ecule and a mesylate anion. The pyrimidine and chromene units of the iclaprim mol-ecule form an orthogonal arrangement [inter-planar angle of 89.67 (6)°], and the 3-nitro-gen position of the pyrimidine ring is protonated. Four distinct N-H⋯O inter-actions and an additional N-H⋯N hydrogen bond connect iclaprim and mesylate mol-ecules to one another, resulting in an infinite hydrogen-bonded mol-ecular tape structure. The central section of the tape is formed by a sequence of fused hydrogen-bonded rings involving four distinct ring types.

Febuxostat ethanol monosolvate.

The title compound, 2-(3-cyano-4-iso-but-oxyphen-yl)-4-methyl-1,3-thia-zole-5-car-b-oxy-lic acid ethanol monosolvate, C16H16N2O3S·C2H6O, (I), displays inter-molecular O-H⋯O and O-H⋯N bonds in which the carboxyl group of the febuxostat mol-ecule and the hydroxyl group of the ethanol mol-ecule serve as hydrogen-bond donor sites. These inter-actions result in a helical hydrogen-bonded chain structure. The title structure is isostructural with a previously reported methanol analogue.

Crystal structure of idelalisib tert-butanol monosolvate dihydrate.

In the title structure, 5-fluoro-3-phenyl-2-[(1S)-1-(9H-purin-6-yl-amino)-prop-yl]quinazolin-4(3H)-one (= idelalisib) tert-butanol monosolvate dihydrate, C22H18FN7O·C4H10O·2H2O, the idelalisib mol-ecule displays planar quinazoline and purine systems which are nearly perpendicular to one another. Seven distinct hydrogen-bonding inter-actions link the idelalisib, t-BuOH and water mol-ecules into a complex chain structure with the topology of a 2,3,4,5-connected 4-nodal net having the point symbol (3.4.52.62)(3.4.52.64.72)(3.5.6)(5).

A novel three-component one-pot synthesis of 1H-imidazol-4-yl-pyridines.

A novel three-component, one-pot condensation yielding 1H-imidazol-4-yl-pyridines from aldehydes, o-picolylamines, and isocyanides is described. The scope and limitations of the reaction have been investigated.

Crystal structure of 3-bromo-2-hy-droxy-benzoic acid.

Mutual carbox-yl-carboxyl O-H⋯O hydrogen bonds link the mol-ecules of the title compound, C7H5BrO3, into centrosymmetric dimers which display a central R 2 (2)(8) ring motif. In addition, there is an intra-molecular hydrox-yl-carboxyl O-H⋯O inter-action present. A comparison with the crystal structures of 59 other substituted derivatives of salicylic acid shows that both the centrosymmetric carbox-yl-carboxyl O-H⋯O dimer and the stacking mode of mol-ecules along the short a axis observed in the title structure are frequent packing motifs in this set.

Crystal structures of Staphylococcusaureus methionine aminopeptidase complexed with keto heterocycle and aminoketone inhibitors reveal the formation of a tetrahedral intermediate.

High-resolution crystal structures of Staphylococcus aureus methionine aminopeptidase I in complex with various keto heterocycles and aminoketones were determined, and the intermolecular ligand interactions with the enzyme are reported. The compounds are effective inhibitors of the S. aureus enzyme because of the formation of an uncleavable tetrahedral intermediate upon binding. The electron densities unequivocally show the enzyme-catalyzed transition-state analogue mimicking that for amide bond hydrolysis of substrates.