14688-31-4

Upstream product

• 28123-63-9 4-chlorobenzohydroximoyl chloride 
• 1173119-91-9 3-(4-chlorophenyl)-5-(trimethylsilanyl)isoxazole 
• 31301-39-0 3-(4-chlorophenyl)-isoxazole 
• 624-31-7 4-tolyl iodide 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 766-97-2 4-n-methylphenylacetylene 
• 3848-36-0 4-chlorobenzaldoxime 
• 873-73-4 4-n-chlorophenylacetylene 
• 104-87-0 4-methyl-benzaldehyde 
• 14688-27-8 N-[1-(4-chloro-phenyl)-ethylidene]-O-(4-methyl-benzoyl)-hydroxylamine 
• 14764-47-7 [3-(4-chloro-phenyl)-5-p-tolyl-isoxazol-4-yl]-p-tolyl-methanone 

Downstream Products

• 65965-62-0 2-(4-{4-[3-(4-chloro-phenyl)-isoxazol-5-yl]-styryl}-phenyl)-[1,2,4]triazolo[1,5-a]pyridine 
• 343624-25-9 5-(4-bromomethyl-phenyl)-3-(4-chloro-phenyl)-isoxazole 
• 1439552-58-5 methyl 5-(4-chlorophenyl)-4-(4-methylbenzoyl)-1H-pyrrole-2-carboxylate 
• 343767-71-5 2-chloro-N-{4-[3-(4-chloro-phenyl)-isoxazol-5-yl]-benzylidene}-aniline 
• 343624-27-1 4-[3-(4-chloro-phenyl)-isoxazol-5-yl]-benzaldehyde 
• 71944-11-1 3-(4-chloro-phenyl)-5-{4-[4-(3-phenyl-pyrazol-1-yl)-styryl]-phenyl}-isoxazole 
• 65204-46-8 4-(4-{4-[3-(4-chloro-phenyl)-isoxazol-5-yl]-styryl}-phenyl)-2-phenyl-2H-[1,2,3]triazole 

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.

Palladium-Catalyzed Direct C-H Arylation of Isoxazoles at the 5-Position

A palladium-catalyzed direct arylation of isoxazoles with aryl iodides has been achieved. The C-H bond at the 5-position is activated selectively to give coupling products in moderate to good yields. This direct arylation was applied to the synthesis of a spiro-type chiral ligand, which proved to be most effective to the palladium-catalyzed tandem cyclization of a dialkenyl alcohol.

Preparation of 3,5-disubstituted pyrazoles and isoxazoles from terminal alkynes, aldehydes, hydrazines, and hydroxylamine

The reaction of terminal alkynes with n-BuLi, and then with aldehydes, followed by the treatment with molecular iodine, and subsequently hydrazines or hydroxylamine provided the corresponding 3,5-disubstituted pyrazoles or isoxazoles in good yields with high regioselectivity, through the formations of propargyl secondary alkoxides and α-alkynyl ketones. The present reactions are one-pot preparation of 3,5-disubstituted pyrazoles from terminal alkynes, aldehydes, molecular iodine, and hydrazines, and 3,5-disubstituted isoxazoles from terminal alkynes, aldehydes, molecular iodine, and hydroxylamine.