5447-76-7

Usage

InChI:InChI=1/C6H11NO3/c1-3-10-6(8)4-5(2)7-9/h9H,3-4H2,1-2H3/b7-5-

Upstream product

• 141-97-9 ethyl acetoacetate 

Downstream Products

• 36771-29-6 4-cyclohex-1-enyl-3-methyl-2H-isoxazol-5-one; compound with morpholine (1:1) 
• 91332-07-9 1-(α-Imino-benzyl)-2-oximino-buttersaeureamid 
• 604787-00-0 C₁₃H₁₇NO₅S 
• 7664-41-7 ammonia 
• 141-97-9 ethyl acetoacetate 
• 65576-89-8 1-amino-1-methylethylphosphinic acid 
• 94650-45-0 3-amino-3-hydrohydroxyphosphorylbutyric acid 
• 1153734-28-1 2-(2-chloro-phenyl)-5-methyl-1H-imidazole-4-carboxylic acid ethyl ester 
• 17975-50-7 4-(o-hydroxyphenylmethylidene)-3-methylisoxazol-5(4H)-one 
• 17975-49-4 4-{1-[4-(dimethylamino)phenyl]methylidene}-3-methyl-5-isoxazolone 
• 31867-76-2 4-(4-hydroxy-3-methoxybenzylidene)-3-methylisoxazol-5(4H)-one 
• 128156-28-5 3-methyl-4-(3,4-dimethoxyphenyl)methyleneisoxazol-5-(4H)-one 
• 10169-97-8 4?(4?(bis(2?chloroethyl)amino)benzylidene)?3?methylisoxazol?5(4H)?one 
• 16430-09-4 3-methyl-4-(1-phenylmethylidene)-5-isoxazolone 

Relevant academic research and scientific papers

Facile and expedient synthesis of α,β-unsaturated isoxazol-5(4H)-ones under mild conditions

Abstract: It was found that nano-SiO2–H2SO4 was catalyzed by the three-component cyclocondensation of aryl/heteroaryl aldehydes, hydroxylamine hydrochloride, and β-ketoesters toward the synthesis of α,β-unsaturated?isoxazol-5(4H)-ones under green conditions. The reaction yielded the corresponding heterocycles at room temperature in relatively shorter reaction times. It merits mentioning that the mild conditions allow the synthesis of several α,β-unsaturated?isoxazol-5(4H)-ones using this method. In this study, some new derivatives of isoxazolones were also synthesized and characterized. It is efficient, clean, simple, safe, and ecologically friendly. This straightforward method is cost-effective and requires no preparation of reactants. The three-component annulation was performed without using energy sources, for example, heat, ultrasound wave, and microwave irradiation. Graphic abstract: [Figure not available: see fulltext.].

Enantioselective Synthesis of Functionalized Diazaspirocycles from 4-Benzylideneisoxazol-5(4H)-one Derivatives and Isocyanoacetate Esters

Enantioenriched spirocyclic compounds bearing three contiguous stereocenters and high functionalization were obtained through a formal [3+2] cycloaddition reaction catalyzed by a cooperative system. The spiro compounds were synthesized from 4-arylideneisoxazol-5-ones and isocyanoacetate esters using a bifunctional squaramide/Br?nsted base organocatalyst derived from a Cinchona alkaloid and silver oxide as Lewis acid. This method afforded two out of the four possible diastereomers with good yields and high enantiomeric excess for both diastereomers. (Figure presented.).

Organocatalyzed nucleophilic addition of pyrazoles to 2: H -azirines: Asymmetric synthesis of 3,3-disubstituted aziridines and kinetic resolution of racemic 2 H -azirines

The first organocatalytic asymmetric nucleophilic addition of arylpyrazoles to 2H-azirines and kinetic resolution of racemic 2H-azirines have been realized. Chiral aziridines were obtained with up to 98% yields and up to 99.9% ee. Meanwhile, simply changing the ratio of reactants, optically active 2H-azirines were recovered in good yields with excellent enantioselectivities.

Rh(ii)-catalyzed cycloadditions of 1-tosyl 1,2,3-triazoles with 2H-azirines: Switchable reactivity of Rh-azavinylcarbene as [2C]- or aza-[3C]-synthon

The Rh(ii)-catalyzed formal [3+2] and [3+3] cycloadditions of 1-tosyl 1,2,3-triazoles with 2H-azirines have been developed, which enable the efficient synthesis of polysubstituted 3-aminopyrroles and 1,2-dihydropyrazines, respectively. The reported [3+2] cycloaddition represents the first application of 1-sulfonyl 1,2,3-triazole as a [2C]-component in relevant cycloaddition reactions. This journal is

RhII-catalyzed [3+2] cycloaddition of 2 H-azirines with N-sulfonyl-1,2,3-triazoles

RhII-catalyzed intermolecular [3+2] cycloaddition of 2 H-azirines with N-sulfonyl-1,2,3-triazoles is disclosed, in which a series of fully functionalized pyrroles is produced via rhodium azavinyl carbene intermediates. A distinct feature of this reaction is that the azavinyl carbene serves as a [2 C] equivalent, instead of as [1 C] or aza-[3 C] synthons, which have been reported previously in cyclopropanations and [3 + n] cycloadditions. Moreover, this methodology has also been successfully applied in the total synthesis of URB447 as well as the formal synthesis of Atorvastatin (Lipitor).

Palladium-catalyzed allylation of 3-hydroxyisoxazole, 5-isoxazolone and 5-pyrazolone systems

Kinetic vs. thermodynamic control and steric hindrance are factors that determine the regioselectivity of the Pd(O)-catalyzed allylation of ambident heterocycles of the 3-hydroxyisoxazole, 5-isoxazolone and 5-pyrazolone series.