Synthesis of 3-Hydroxy-4-arylquinolin-2-ones Including Viridicatol via a Darzens Condensation/Friedel-Crafts Alkylation Strategy.

The new efficient synthesis of biologically important 3-hydroxy-4-arylquinolin-2-ones through the Darzens condensation (epoxidation) of dichloroacetanilides with aromatic aldehydes followed by one-pot dechlorative epoxide-arene cyclization is described. This methodology has been utilized for the synthesis of naturally occurring viridicatol, a fungal metabolite isolated from the penicillium species.

Structure of copper(II) complexes grown from ionic liquids - 1-ethyl-3-methyl-imidazolium acetate or chloride.

Crystals of four new copper(II) complexes have been grown from copper(II) acetate/chloride-1-ethyl-3-methyl-imidazolium acetate/chloride-water systems and characterized by X-ray analysis. The first complex, bis-(1-ethyl-3-methyl-imidazolium) tetra-μ-acetato-bis[chloridocuprate(II)], [Emim][Cu(CHO)Cl] () (Emim is 1-ethyl-3-methyl-imidazolium, CHN), contains [Cu(CHO)Cl] coordination anions with a paddle-wheel structure and ionic liquid cations. Two of the synthesized complexes are one-dimensional polymers, namely -poly[1-ethyl-3-methyl-imidazolium [[tetra-μ-acetato-dicuprate(II)]-μ-chlorido] monohydrate], {[Emim][Cu(CHO)Cl]·HO} (), and -poly[1-ethyl-3-methyl-imidazolium [[tetra-μ-acetato-dicuprate(II)]-μ-acetato]], {[Emim][Cu(CHO)]} ().

Rearrangement of quinoxalin-2-ones when exposed to enamines generated in situ from ketones and ammonium acetate: method for the synthesis of 1-(pyrrolyl)benzimidazolones.

The reaction of 3-benzoylquinoxalin-2(1H)-ones with enamines (generated in situ from ammonium acetate and the corresponding methylaryl(hetaryl)ketones) proceeds smoothly to give the corresponding substituted 1-(pyrrolyl)benzimidazolone derivatives in moderate yields through the novel rearrangement of 3-benzoylquinoxalin-2(1H)-ones involving a dual cleavage of the C3═N4 and C2-C3 bonds under mild conditions.

Alternating stereoselective self-assembly of SSSS/RRRR or RSSR isomers of tetrakisphosphines in the row of 14-, 16-, 18- and 20-membered macrocycles.

Novel 18- and 20-membered P,N-macrocycles have been obtained stereoselectively by covalent self-assembly of α,ω-bisphosphines, formaldehyde and benzylamine. Alternating SSSS/RRRR or RSSR diastereomers were formed in the row of the 14-, 16-, 18- and 20-membered macrocyclic aminomethylphosphines. For the first time it was demonstrated that the stereochemical result of the reaction depends on the even or odd number of the methylene groups between the two chiral phosphorus atoms in the initial α,ω-bisphosphines.

New functional cyclic aminomethylphosphine ligands for the construction of catalysts for electrochemical hydrogen transformations.

Eight-membered cyclic functional bisphosphines, namely 1,5-di-aryl-3,7-di(2-pyridyl)-1,5-diaza-3,7-diphosphacyclooctanes (aryl=2-pyridyl, m-tolyl, p-tolyl, diphenylmethyl, benzyl, (R)-(+)-(α-methyl)benzyl), with 2-pyridyl substituents on the phosphorus atoms have been synthesized by condensation of 2-pyridylphosphine, formaldehyde, and the corresponding primary amine. The structures of some of these bisphosphines have been investigated by X-ray crystallography. The bisphosphines readily form neutral P,P-chelate complexes [(κ(2)-P,P-L)MCl2], cationic bis-P,P-chelate complexes [(κ(2)-P,P-L)2 M](2+), or a five-coordinate complex [(κ(2)-P,P-L)2 NiBr]Br.

The C-H bond activation in 1-ethyl-3-methylimidazolium acetate-copper(II) acetate-water-air (dioxygen) systems.

Ionic liquid (1-ethyl-3-methylimidazolium acetate, [C2C1im][AcO])-copper(ii) diacetate monohydrate-water-air (O2) systems have been investigated by (13)C NMR, EPR, spectrophotometry, HPLC, and synthetic chemistry methods at different temperatures. The C-H bond activation of [C2C1im](+) with the formation of the unusual dication 1,1'-diethyl-3,3'-dimethyl-2,2'-biimidazolium ([(C2C1im)2](2+)) at 50 °C and 1-ethyl-3-methyl-1H-imidazol-2(3H)-one (C2C1imO) at 50-85 °C was revealed. Two new complexes with the above compounds, [(C2C1im)2][Cu(AcO)4] and Cu2(AcO)4(C2C1imO)2, were isolated from the systems and characterized by X-ray structural analysis.