10004-45-2

Usage

General Description

3(2H)-Isoxazolone, 5-ethyl-, also known as ethyl isoxazol-3(2H)-one, is a chemical compound with the molecular formula C7H9NO2. It is categorized under the organic compound class known as isoxazolones, which are compounds containing an isoxazole ring fused to a ketone. It is mostly used as an intermediate in the pharmaceutical industry and can be used for organic synthesis. The physical properties of 3(2H)-Isoxazolone, 5-ethyl- include a heavy atom count of 10, a topological polar surface area of 38.3, and four rotatable bonds. Its stability is influenced by light, heat, and moisture; hence it should be stored in a cool, dry place in a tightly closed container.

Upstream product

• 95395-85-0 N-benzyloxy-3-oxopentanamide 
• 72324-46-0 6-ethyl-2,2-dimethyl-2H,4H-1,3-dioxin-4-one 
• 66696-76-2 5-(1-hydroxypropylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 95395-87-2 N-hydroxy-3-oxopentanamide 

Relevant academic research and scientific papers

A novel route to 5-substituted 3-isoxazolols. Cyclization of N,O-diBoc β-keto hydroxamic acids synthesized via acyl Meldrum's acids

3-Isoxazolols are most often synthesized from a β-keto ester and hydroxylamine. This cyclization typically gives rise to a major byproduct, the corresponding 5-isoxazolone. We have found that N,O-diBoc-protected β- keto hydroxamic acids can be synthesized and cyclized to 5-substituted 3- isoxazolols without formation of any byproduct. We present a novel and versatile three-step procedure in which carboxylic acid derivatives are converted into acyl Meldrum's acids which, upon aminolysis with N,O-bis(tert- butoxycarbonyl)hydroxylamine, lead to the N,O-diBoc-protected β-keto hydroxamic acids. These hydroxamic acid analogues were then, upon treatment with hydrochloric acid, cyclized to the corresponding 5-substituted 3- isoxazolols.

Synthesis of β-Ketocarboxamide Derivatives Using 2,2-Dimethyl-2H,4H-1,3-dioxin-4-ones

Thermal reaction of 2,2-dimethyl-2H,4H-1,3-dioxin-4-ones (1) with amines was studied.Acylketenes 2, generated by heating of 1, reacted with anilines and benzylamine to give the corresponding β-ketocarboxamides (3,4, and 5) in good yields.The reaction of 1 with ammonia gave 3-amino-2-alkenamides (7), which were hydrolyzed to β-ketocarboxamides (6).The former products 7 were readily transformed to the 6-substituted 2-methyl-3H-pyrimidin-4-ones (9) via the 3-acetamido-2-alkenamides (8).Acylation of O-benzylhydroxylamine with 1 gave the β-ketohydroxamic acids 10.Debenzylation of 10 followed by cyclization gave rise to 5-alkyl-3-hydroxyisoxazoles (12).The reaction of 1 with amides gave the corresponding N-acetylated amides (13). Keywords --- 2H,4H-1,3-dioxin-4-one; thermal fragmentation; acylketene; acylation; carboxamide; hydroxamic acid; 3-hydroxyisoxazole; 3H-pyrimidin-4-one