51978-97-3

Upstream product

• 1123-49-5 3,5-dimethyl-4-nitroisoxazole 
• 104-88-1 4-chlorobenzaldehyde 
• 300-87-8 3,5-dimethyl-1,2-oxazole 
• 123-54-6 acetylacetone 

Downstream Products

• 103806-28-6 2-acetyl-3-(4-chlorophenyl)-4-(3-methyl-4-nitroisoxazol-5-yl)butyric acid ethyl ester 
• 79510-70-6 5-(4-Chloro-phenyl)-3'-methyl-4'-nitro-3-phenyl-4,5-dihydro-[4,5']biisoxazolyl 
• 79510-59-1 3-[1-(4-chlorophenyl)-2-(3-methyl-4-nitroisoxazol-5-yl)ethyl]pentane-2,4-dione 
• 86453-98-7 5-[1,2-Dibromo-2-(4-chloro-phenyl)-ethyl]-3-methyl-4-nitro-isoxazole 
• 914482-18-1 5-[2-(4-chlorophenyl)-2-(3,5-dimethyl-1H-pyrazol-4-yl)-ethyl]-3-methyl-4-nitroisoxazole 
• 914482-19-2 5-[2-(4-chlorophenyl)-2-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)-ethyl]-3-methyl-4-nitroisoxazole 
• 78636-38-1 5-[2-(3,5-dimethylisoxazol-5-yl)-2-(4-chlorophenyl)ethyl]-3-methyl-4-nitroisoxazole 
• 117838-23-0 3-(4-Chloro-phenyl)-2-{1-[(Z)-hydroxyimino]-ethyl}-4-(3-methyl-4-nitro-isoxazol-5-yl)-butyric acid ethyl ester 
• 117869-56-4 3-[1-(4-Chloro-phenyl)-2-(3-methyl-4-nitro-isoxazol-5-yl)-ethyl]-7-hydroxy-2-methyl-chromen-4-one 
• 3240-10-6 (4-chlorophenyl)propiolic acid 
• 1021951-84-7 (1R,2S)-1-(4-chlorophenyl)-2-(3-methyl-4-nitro-isoxazol-5-yl)-ethane-1,2-diol 
• 53558-04-6 5-[(E)-2-(4-Chloro-phenyl)-vinyl]-3-methyl-isoxazol-4-ylamine 
• 1229422-33-6 1-(4-chloro-phenyl)-2-(3-methyl-4-nitro-isoxazol-5-yl)ethanesulfonic acid 
• 1314230-99-3 5-(2-benzylsulfanyl-2-(4-chlorophenyl)ethyl)-3-methyl-4-nitroisoxazole 

Relevant academic research and scientific papers

Phosphine-Catalyzed [3 + 2] Annulation of Morita-Baylis-Hillman Carbonates with Isoxazole-Based Alkenes

A phosphine-catalyzed [3 + 2] annulation of Morita-Baylis-Hillman (MBH) carbonates with 3-methyl-4-nitro-5-styrylisoxazoles has been developed to afford various multifunctional isoxazoles in moderate to good yields with moderate to excellent diastereoselectivities. With a spirocyclic chiral phosphine as the catalyst, up to 89% ee was obtained.

Structure–activity relationships of GPX4 inhibitor warheads

Direct inhibition of GPX4 requires covalent modification of the active-site selenocysteine. While phenotypic screening has revealed that activated alkyl chlorides and masked nitrile oxides can inhibit GPX4 covalently, a systematic assessment of potential electrophilic warheads with the capacity to inhibit cellular GPX4 has been lacking. Here, we survey more than 25 electrophilic warheads across several distinct GPX4-targeting scaffolds. We find that electrophiles with attenuated reactivity compared to chloroacetamides are unable to inhibit GPX4 despite the expected nucleophilicity of the selenocysteine residue. However, highly reactive propiolamides we uncover in this study can substitute for chloroacetamide and nitroisoxazole warheads in GPX4 inhibitors. Our observations suggest that electrophile masking strategies, including those we describe for propiolamide- and nitrile-oxide-based warheads, may be promising for the development of improved covalent GPX4 inhibitors.

Tandem grinding reactions involving aldol condensation and Michael addition in sequence for synthesis of 3,4,5-trisubstituted isoxazoles

A one-pot, base-catalyzed, tandem grinding process involving carrying out aldol condensation and Michael addition in sequence to produce 3,4,5-trisubstituted isoxazoles from 3,5-dimethyl-4-nitroisoxazole, aromatic aldehydes and activated methylene compoun

An efficient solvent-free synthesis of 3-methyl-4-nitro-5-styrylisoxazoles using solid nano-titania

Abstract: An efficient and solvent-free procedure for the synthesis of 3-methyl-4-nitro-5-styrylisoxazoles using nano-titania as solid support and recyclable catalyst is presented. This method provides clean, simple, solvent-free and useful alternative to

'On water' direct vinylogous Henry (nitroaldol) reactions of 3,5-dimethyl-4-nitroisoxazole with aldehydes and trifluoromethyl ketones

An efficient 'on water'-promoted direct catalytic vinylogous addition of 3,5-dimethyl-4-nitroisoxazole to aldehydes and trifluoromethyl ketones was described, giving Henry (nitroaldol) adducts in excellent yields. The trifluoromethyl tertiary alcohol prod

Catalytic enantioselective addition of isocyanoacetate to 3-methyl-4-nitro-5-styrylisoxazoles under phase transfer catalysis conditions

The reaction between 3-methyl-4-nitro-5-styrylisoxazoles and ethyl isocyanoacetate proceeded under phase transfer catalysis to give enantioenriched monoadducts in high enantiomeric excess (up to 99% ee). The resulting adducts were subsequently cyclised to give 2,3-dihydropyrroles and substituted pyrrolidines in identical high ees and as a single diastereoisomer.

One-pot synthesis of functionalized isoxazole-thiolane hybrids via Knoevenagel condensation and domino sulfa-1,6-Michael/intramolecular vinylogous Henry reactions

One-pot synthesis of highly functionalized tetrahydrothiophene (thiolane) derivatives conjugated with biologically useful isooxazole are reported via the Knoevenagel condensation followed by domino sulfa-1,6-Michael/intramolecular vinylogous Henry reactio

Organocatalyzed asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam

Highly efficient asymmetric vinylogous 1,6-Michael addition of α,β-unsaturated γ-butyrolactam to 3-methyl-4-nitro-5-alkenyl- isoxazoles and Michael addition to trichloromethyl ketones by using a chiral quinine-derived squaramide organocatalyst were described, giving products with high diastereo- and enantioselectivities (up to >25:1 dr and 96% ee).

Multi-component synthesis and in vitro and in vivo anticancer activity of novel arylmethylene bis-isoxazolo[4,5-b]pyridine-N-oxides

A three component one-pot protocol has been investigated for the synthesis of arylmethylene bis-isoxazolo[4,5-b]pyridine-N-oxides 1 from the commercially available materials. The title compounds 1 were also synthesized by a step-wise method and found to b

Trifluoromethylation of aromatic isoxazoles: Regio- and diastereoselective route to 5-trifluoromethyl-2-isoxazolines

It all adds up: The activation of aromatic isoxazoles with a nitro group at the 4-position has enabled the first regio- and diastereoselective trifluoromethylation at the 5-position of isoxazoles by nucleophilic addition using Me3SiCF3 (see scheme; DMF=N,N′- dimethylformamide). The process was demonstrated with a broad range of 3,5-aromatic, heteroaromatic and aliphatic substrates.