40435-26-5

Upstream product

• 14337-43-0 ethyl 2-chloro-2-(hydroxyimino)acetate 
• 140-88-5 ethyl acrylate 
• 626-35-7 nitroacetic acid ethyl ester 
• 95080-93-6 ethyl chlorooximidoacetate 
• 623-33-6 glycine ethyl ester hydrochloride 
• 623-73-4 diazoacetic acid ethyl ester 
• 31767-14-3 ethyl 2-(hydroxyimino)acetate 
• 51026-98-3 ethyl 2-nitro-3-oxobutyrate 

Relevant academic research and scientific papers

Solid base-catalyzed synthesis of 5-substituted 4,5-dihydroisoxazoles

We present a new synthetic route for the preparation of 5-substituted 4,5-dihydroisoxazole derivatives starting from ethyl nitroacetate and alkenes in the presence of modified Mg:Al 3:1 hydrotalcite.

Acyclic nitronate olefin cycloaddition (ANOC): regio- And stereospecific synthesis of isoxazolines

We report the first demonstrations of intra- and intermolecular acyclic nitronate olefin cycloaddition (ANOC) reactions that enable the highly efficient syntheses of isoxazolines bearing various functional groups. This general approach to accessing γ-lactone fused isoxazolines was hitherto unprecedented. The room temperature transformations reported herein exhibit wide substrate scopes, as evidenced by more than 70 examples, including the generation of five tricyclic isoxazolines. The robustness of this methodology was confirmed by a series of trials that afforded highly functionalized isoxazolines. Both experimental results and density functional theory calculations indicate that these transformations proceed via the in situ formation of acyclic nitronates together with concerted [3+2] cycloaddition and tert-butyloxy group elimination processes to give regio- and stereospecificity. This journal is

Method for preparing isoxazoline

The invention relates to a method for preparing isoxazoline, which comprises the steps of reacting olefin, a diazo compound and tert-butyl nitrite in an organic solvent at the temperature of 25-50 DEGC under the action of a Lewis acid catalyst to obtain isoxazoline after complete reaction. Lewis acid is used as a catalyst for synthesizing isoxazoline, reaction conditions are mild and can be carried out under the condition that the temperature is as low as the room temperature, use of transition metal is avoided, and the product yield is high.

Oxidize Amines to Nitrile Oxides: One Type of Amine Oxidation and Its Application to Directly Construct Isoxazoles and Isoxazolines

A facile oxidative heterocyclization of commercially available amines and tert-butyl nitrite with alkynes or alkenes leading to isoxazoles or isoxazolines is described. The unprecedented strategy of the oxidation of an amine directly to a nitrile oxide was used in this cyclization process. This reaction is highly efficient, regiospecific, operationally simple, mild, and tolerant of a variety of functional groups. Control experiments support a nitrile oxide intermediate mechanism for this novel class of oxidative cyclization reactions. Moreover, synthetic applications toward bioactive molecular skeletons and the late-stage modification of drugs were realized.

From Alkenes to Isoxazolines via Copper-Mediated Alkene Cleavage and Dipolar Cycloaddition

An unprecedented copper-mediated anion transformation is reported, along with selective C= C double bond cleavage and dipolar cycloaddition reaction from simple alkenes and inexpensive copper nitrate. Various transformations demonstrate the generality of this method. Further mechanistic investigation indicates a novel ionic pathway for alkene cleavage and highlights the coeffect of iodide and boric acid as additives on the inhibition of well-documented competitive nitration byproducts.

Effect of aqueous polyethylene glycol on 1,3-dipolar cycloaddition of benzoylnitromethane/ethyl 2-nitroacetate with dipolarophiles: Green synthesis of isoxazoles and isoxazolines

A 1:1 mixture of water-polyethylene glycol (PEG) facilitated the 1,3-dipolar cycloaddition of benzoylnitromethane/ethyl 2-nitroacetate with terminal alkynes or alkenes leading to isoxazoles or isoxazolines under green conditions. The methodology is free f

Cycloaddition reactions of nitrosoalkenes, azoalkenes and nitrile oxides mediated by hydrotalcite

Mg:Al 3:1 hydrotalcite (Ht), used in catalytic quantities, promotes the generation of nitrosoalkenes, azoalkenes and nitrile oxides. These can be intercepted in situ by heterocycles and olefins in [4+2] and [3+2] cycloaddition reactions, producing dihydro

1,3-Cycloaddition of nitrile oxides in ionic liquids. An easier route to 3-carboxy isoxazolines, potential constrained glutamic acid analogues

Several improvements in the cycloaddition of carboethoxyformonitrile oxide (CEFNO) with different alkenes are observed in the ionic liquids [bmim][BF4] and [bmim][PF6]. The possibility of obtaining good yields of the corresponding is

Oxidative and dehydrative cyclizations of nitroacetate esters with Mn(OAc)3

Reaction of α-unsubstituted nitroacetates with Mn(OAc)3 gives mixtures of isoxazolines, formed by dehydration to a nitrile oxide that undergoes cycloaddition, and isoxazoline oxides or cyclopropane, formed by oxidative cyclization. Oxidative cyclization is favored with electron-rich alkenes and cycloaddition with the nitrile oxide to give isoxazolines is favored with electron-poor alkenes. On the other hand, α-substituted nitroacetates cannot dehydrate and undergo only radical reactions.

Generation of nitrile oxides from oxime derivatives by the oxidation with ammonium hexanitratocerate(IV)

Aromatic and aliphatic nitrile oxides are generated by the oxidation of α-hydroxyimino carboxylic acid with ammonium hexanitratocerate(IV). They react with olefinic and acetylenic dipolarophiles to give the corresponding cycloaddition products in good yield. The oxidation of α-oxo aldoximes also affords α-oxo carbonitrile oxides.