A new Cu-catalyzed efficient protocol is described for the transformation of oximes to the corresponding carbonate derivatives. Diisopropyl azodicarboxylate acted as a selective new precursor for the synthesis of oxime carbonates in high yields. The O-H bond cleavage and O-C bond formation occur in the presence of a copper catalyst providing a synthetically useful process, which tolerates a wid...

A photoinduced cascade strategy leading to a variety of differentially functionalised nitriles and ketones has been developed. These reactions rely on the oxidative generation of iminyl radicals from simple oximes. Radical transposition by C(sp3 )-(sp3 ) and C(sp3 )-H bond cleavage gives access to distal carbon radicals that undergo SH 2 functionalisations. These mild, visible-light-mediated pr...

A direct strategy to obtain N-acyl amino acid oxime esters has been developed through the dynamic kinetic resolution of azlactones with oximes. In the presence of a chiral bisguanidinium salt catalyst, a variety of chiral N-acyl amino acid oxime esters were generated in excellent enantiomeric excesses (up to 97%) and high yields (up to 99%). The active oxime esters could be used in dipeptide sy...

In both solution and the solid phase, a variety of ketone oxime anions have been treated with 4-substituted-2-fluorobenzonitriles to give the corresponding nucleophilic aromatic substitution aryloxime adducts. Under aqueous acidic conditions, these adducts underwent cyclization to give the corresponding ketones. Suzuki and amide coupling reactions were also successfully performed on two resin-b...

Nitrile oxides were generated by the catalytic dehydrogenation of aromatic aldehyde oximes 2a-g with chloramine-T as oxidizing agent. The 1,3-dipolar cycloaddition of in situ generated nitrile oxides with ethyl oleate 1 produced a series of new ethyl 8-(3-aryl-4-octyl-4,5-dihydroisoxazol-5-yl)octanoate 3a-g in 6584% yield. Some of the synthesized cycloadducts have exhibited moderate to good ant...

Organophosphate poisoning is characterised for the most part, by acute incidents. Management is by way of first aid (in mild poisoning) and use of atropine with or without the oximes, (in moderate to severe poisoning). Of late, it has become apparent that subchronic and chronic organophosphate poisoning are a common manifestation. This review paper summarises this triphasic nature of organophos...

We describe herein a palladium-catalyzed Heck-type reaction of O-acetyl ketoximes and allylic alcohols to synthesise pyridines. This protocol allows the robust synthesis of pyridines and azafluorenones in good to excellent yields with tolerance of various functional groups under mild conditions. The reaction is supposed to go through an oxidative addition of oximes to palladium(0) complexes, ge...

The synthesis of a set of 1-aryl-2-aryl(3-pyridyl)ethanones 1-5 and the corresponding ketoximes 6-9 is reported. Structural studies of oximes 6, 7 and 9 were performed in solution using (1)H-NMR and in the solid state by X-ray crystallography, providing evidence of H-bonding networks. The crystal packing was controlled by homomeric intermolecular oxime...oxime H-bond interactions for 6 and coop...

Treatment of oximes with hypervalent iodine leads to substituted isoxazoles via rapid formation of nitrile oxides. Reaction with terminal alkynes led to a series of 3,5-disubstituted isoxazoles with complete regioselectivity and high yield, in a procedure mild enough to prepare a range of nucleoside and peptide conjugates. Exceptionally high reaction rates were found for the formation of 3,4,5-...

In the title compound, C(13)H(11)ClN(2)O(3), the nine-membered bicycle includes an oxime group having the C=N group in an E configuration. The isoxazole ring is almost planar [r.m.s. deviation = 0.0056 Å]; the dihedral angle between the isoxazole and 4-chloro-phenyl ring is 75.60 (5)°. In the crystal, inter-molecular O-H⋯N(isoxazole) hydrogen bonds give rise to chains running along the b axis.