Isoxazoles from 1,1-disubstituted bromoalkenes

Investigation of facet effects on the catalytic activity of Cu2O nanocrystals for efficient regioselective synthesis of 3,5-disubstituted isoxazoles.

Cubic, octahedral, and rhombic dodecahedral Cu2O nanocrystals bound by respectively {100}, {111}, and {110} facets were successfully employed to catalyze the [3 + 2] cycloaddition reaction for the regioselective synthesis of 3,5-disubstituted isoxazoles. Surfactant-free nanocrystals having the same total surface area were used for the catalysis. Strongly facet-dependent organocatalytic activity...

Synthesis of isoxazoles by hypervalent iodine-induced cycloaddition of nitrile oxides to alkynes.

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-...

Isoxazole derivatives as new nitric oxide elicitors in plants

Several 3,5-disubstituted isoxazoles were obtained in good yields by regiospecific 1,3-dipolar cycloaddition reactions between aromatic nitrile oxides, generated in situ from the corresponding hydroxyimidoyl chlorides, with non-symmetrical activated alkynes in the presence of catalytic amounts of copper(I) iodide. Effects of 3,5-disubstituted isoxazoles on nitric oxide and reactive oxygen speci...

Simple two-step synthesis of 2,4-disubstituted pyrroles and 3,5-disubstituted pyrrole-2-carbonitriles from enones

The cyclocondensation of enones with aminoacetonitrile furnishes 3,4-dihydro-2H-pyrrole-2-carbonitriles which can be readily converted to 2,4-disubstituted pyrroles by microwave-induced dehydrocyanation. Alternatively, oxidation of the intermediates produces 3,5-disubstituted pyrrole-2-carbonitriles.

Rhodium-Catalyzed Synthesis of 2,3-Disubstituted Indoles from β,β-Disubstituted Stryryl Azides**