15911-11-2

Usage

Uses

Used in Organic Synthesis:
5-Ethyl-isoxazole-3,4-dicarboxylic acid diethyl ester serves as a valuable building block in organic synthesis, facilitating the creation of a diverse array of chemical compounds. Its unique structure allows for various chemical reactions, making it a key component in the synthesis of complex organic molecules.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 5-Ethyl-isoxazole-3,4-dicarboxylic acid diethyl ester is utilized as an intermediate. Its role in the synthesis of active pharmaceutical ingredients is crucial, contributing to the development of new medications that address a range of health conditions.
Used in Agricultural Chemicals:
5-ETHYL-ISOXAZOLE-3,4-DICARBOXYLIC ACID DIETHYL ESTER also finds application in the agricultural sector, where it is employed as an intermediate in the production of agricultural chemicals. Its involvement in the synthesis of pesticides, herbicides, and other agrochemicals underscores its importance in enhancing crop protection and yield.
Used in Specialty Chemicals:
5-Ethyl-isoxazole-3,4-dicarboxylic acid diethyl ester extends its utility to the specialty chemicals market, where it is leveraged in the formulation of unique chemical products that cater to specific industrial needs. Its adaptability in various chemical processes highlights its broad applicability across different chemical specialties.

InChI:InChI=1/C9H11NO4/c1-4-13-9(12)8-7(5(2)11)6(3)14-10-8/h4H2,1-3H3

Upstream product

• 216962-12-8 3-isoxazolecarboxylic acid 5-methyl-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)-ethyl ester 
• 14337-43-0 ethyl 2-chloro-2-(hydroxyimino)acetate 
• 123-54-6 acetylacetone 
• 95080-93-6 ethyl chlorooximidoacetate 
• 626-35-7 nitroacetic acid ethyl ester 
• 861135-87-7 chlorohydroxyimino-acetic acid ethyl ester 
• 1118-67-8 sodium (Z)-4-oxopent-2-en-2-olate 

Downstream Products

• 15911-14-5 5-methyl-4-[1-(phenyl-hydrazono)-ethyl]-isoxazole-3-carboxylic acid ethyl ester 
• 15911-15-6 3,4-dimethyl-6-phenylisoxazolo[3,4-d]pyridazin-7(6H)-one 
• 25505-97-9 3,4,6-trimethylisoxazolo<3,4-d>pyridazin-7(6H)-one 
• 115697-68-2 4-(2-Bromo-acetyl)-5-methyl-isoxazole-3-carboxylic acid ethyl ester 
• 263890-17-1 3,4-dimethyl-6-(2,4-difluorophenyl)isoxazolo[3,4-d]pyridazin-7(6H)-one 
• 265126-63-4 3,4-dimethyl-6-(4-fluorophenyl)isoxazolo[3,4-d]pyridazin-7(6H)-one 
• 1208102-86-6 5-methyl-4-(1-[(2-nitro-phenyl)-hydrazono]-ethyl)-isoxazole-3-carboxylic acid ethyl ester 
• 1208102-85-5 5-methyl-4-(1-[(4-nitro-phenyl)-hydrazono]-ethyl)-isoxazole-3-carboxylic acid ethyl ester 
• 263890-31-9 3,4-dimethyl-6-(4-nitrophenyl)isoxazolo[3,4-d]pyridazin-7(6H)-one 
• 263890-21-7 3,4-dimethyl-6-p-tolylisoxazolo[3,4-d]pyridazin-7(6H)-one 
• 263755-65-3 3,4-dimethyl-6-(4-methoxyphenyl)isoxazolo[3,4-d]pyridazin-7(6H)-one 
• 1208102-76-4 3,4-dimethyl-6-(4-(trifluoromethyl)phenyl)isoxazolo[3,4-d]pyridazin-7(6H)-one 
• 1340474-37-4 ethyl 5-(3-methoxybenzyl)-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)-1,2-oxazole-3-carboxylate 
• 1340474-38-5 ethyl 5-(4-methoxybenzyl)-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)-1,2-oxazole-3-carboxylate 

Relevant academic research and scientific papers

Microwave accelerated synthesis of isoxazole hydrazide inhibitors of the system xc-rter: Initial homology model

Microwave accelerated reaction system (MARS) technology provided a good method to obtain selective and open isoxazole ligands that bind to and inhibit the Sxc- antiporter. The MARS provided numerous advantages, including: shorter time, better yield and higher purity of the product. Of the newly synthesized series of isoxazoles the salicyl hydrazide 6 exhibited the highest level of inhibitory activity in the transport assay. A homology model has been developed to summarize the SAR results to date, and provide a working hypothesis for future studies.

Suzuki-Miyaura cross-coupling of benzylic bromides under microwave conditions

A procedure for benzylic Suzuki-Miyaura cross-coupling under microwave conditions has been developed. These conditions allowed for heterocyclic compounds to be coupled. Optimum conditions found were Pd(OAc)2, JohnPhos as the catalyst and ligand

Base- and copper-catalysed condensation of primary activated nitro compounds with enolisable compounds

Primary nitro compounds have not been employed as nitrile oxide precursors in reactions with active methylene compounds because the reagents commonly used as dehydrating agents also react with these dipolarophiles. However, the Cu II-catalysed

Catalytic asymmetric synthesis of glutamate analogues

Utilizing our lateral metalation coupled with Jacobsen's catalytic asymmetric amino nitrile synthesis, we have demonstrated the ability to synthesize isoxazole-containing amino acid glutamate analogues in high yield and high enantiomeric excesses. Chiral

[(3-Chlorophenyl)piperazinylpropyl]pyridazinones and analogues as potent antinociceptive agents

A number of [(3-chlorophenyl)piperazinylpropyl]pyridazinones and the corresponding isoxazolopyridazinones, showing the arylpiperazinyl substructure present in very potent antinociceptive agents reported in the literature, were synthesized and tested for t

An improved procedure for the lateral lithiation of ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate

Ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate was smoothly lithiated at the 5-methyl position, when the 4-acetyl group was protected with a 5,5-dimethyl-1,3-dioxanyl group. The lithio anion was quenched with a variety of electrophiles such as alkyl halides, aldehydes, TMSCl, and Me3SnCl in good to excellent yields. The lithiation of the unprotected compound and the 4-acetyl group protected as 1,3-dioxolanyl both failed. The effects of different bases have been investigated and the addition of LiCl significantly increased yields. Based on variable temperature NMR studies the 5,5-dimethyl-1,3-dioxanyl group appears to occupy a single chair conformation which may facilitate lateral metalation. This represents a facile entry into 5-functionalized 3-isoxazolyl carboxylic acid derivatives as prodrugs for the AMPA glutamate neurotransmitters of the central nervous system.

Lateral lithiation of ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate with 5,5-dimethyl-1,3-dioxanyl as a directing group

Lateral lithiation of ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate, a functionalized isoxazole AMPA analog, occurs cleanly at the C-5 methyl group with 5,5-dimethyl-1,3-dioxanyl as a directing group. The 4-acetyl isoxazole derivatives were transformed selectively by a modified Willgerodt- Kindler reaction into the corresponding homologated methyl esters after deprotection.