42457-26-1

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 59336-59-3 cinnamaldehyde oxime 
• 536-74-3 phenylacetylene 
• 104-55-2 3-phenyl-propenal 
• 13372-81-1 cinnamaldoxime 
• 107487-07-0 (E)-5-phenyl-3-(2-phenylethenyl)-2-isoxazoline 
• 6502-37-0 (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one oxime 

Relevant academic research and scientific papers

Unusual Reactivity of 4-Vinyl Isoxazoles in the Copper-Mediated Synthesis of Pyridines, Employing DMSO as a One-Carbon Surrogate

An efficient protocol for the synthesis of nicotinate derivatives and tetrasubstituted pyridines through a copper-mediated cleavage of isoxazoles has been developed. The highlight of the work is the observation of an unusual reactivity of 4-vinyl isoxazoles under the reaction conditions. DMSO serves as a one-carbon surrogate generating an active methylene group during the reaction to form two C-C bonds. This protocol provides a facile and an expeditious approach for the assembly of densely substituted N-heterocyclic compounds.

Catalyst control in positional-selective C-H alkenylation of isoxazoles and a ruthenium-mediated assembly of trisubstituted pyrroles

High levels of catalyst control are demonstrated in determining the positional selectivity in C-H alkenylation of isoxazoles. A cationic rhodium-mediated, strong-directing group promotes C(sp2)-H activation at the proximal aryl ring whereas, the palladium-mediated electrophilic metallation leads to the C(sp2)-H activation at the distal position of the directing group. Synthetic elaboration of this C-H alkenylation product via ruthenium and copper co-catalysis leads to an efficient method for the assembly of densely substituted pyrroles.

Iron(iii)-catalyzed selective N-O bond cleavage to prepare tetrasubstituted pyridines and 3,5-disubstituted isoxazolines from: N -vinyl-α,β-unsaturated ketonitrones

An iron(iii)-catalyst controlled cyclization and selective N-O bond cleavage of N-vinyl-α,β-unsaturated nitrones has been achieved under mild conditions to access tetrasubstituted pyridines and 3,5-disubstituted isoxazolines in moderate to good yields. The tetrasubstituted pyridines were afforded with FeCl3 as a catalyst while using FeCl3·6H2O combined with 1,10-phenanthroline delivered isoxazolines. The regioselectivity for cyclization of styrenyl groups in N-vinyl-α,β-unsaturated nitrones was completely different during the formation of pyridines and isoxazolines. A rational mechanism for the formation of pyridines and isoxazolines was proposed based on the further control experimental studies. The isoxazolines can be converted to a novel bidentate N-ligand over four steps and an epoxypyridine scaffold was obtained from N-vinyl nitrone when copper(ii) acetate in combination with the prepared bidentate N-ligand was used.

Copper(0) Nanoparticles in Click Chemistry: Synthesis of 3,5-Disubstituted Isoxazoles

An efficient procedure for the synthesis of 3,5-disubstituted isoxazoles via [3+2] cycloaddition reaction of in situ generated nitrile oxides with acetylenes employing readily preparable copper(0) nanoparticles is described. A variety of in situ generated

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