145622-07-7

Upstream product

• 97023-67-1 ethyl 2-(4-methylphenyl)cyclopropane-1-carboxylate 
• 623-73-4 diazoacetic acid ethyl ester 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 104-87-0 4-methyl-benzaldehyde 
• 626-35-7 nitroacetic acid ethyl ester 

Downstream Products

• 88958-15-0 ethyl 5-(4-methylphenyl)isoxazole-3-carboxylate 

Relevant academic research and scientific papers

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

Design, synthesis of novel 4,5-dihydroisoxazole-containing benzamide derivatives as highly potent FtsZ inhibitors capable of killing a variety of MDR Staphylococcus aureus

Antibiotic resistance among clinically significant bacterial pathogens, such as methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant S. aureus (VRSA) is becoming a prevalent threat to public health, and new antibacterial agents with novel mechanisms of action hence are in an urgent need. As a part of continuing effort to develop antibacterial agents, we rationally designed and synthesized two series of 4,5-dihydroisoxazol-5-yl and 4,5-dihydroisoxazol-3-yl-containing benzamide derivatives that targeted the bacterial cell division protein FtsZ. Evaluation of their activity against a panel of Gram-positive and -negative pathogens revealed that compound A16 possessing the 4,5-dihydroisoxazol-5-yl group showed outstanding antibacterial activity (MIC, ≤0.125–0.5 μg/mL) against various testing strains, including methicillin-resistant, penicillin-resistant and clinical isolated S. aureus strains. Besides, further mouse infection model revealed that A16 could be effective in vivo and non-toxic to Hela cells. Finally, a detailed discussion of structure-activity relationships was conducted, referring to the docking results. It is worth noting that substituting a 4,5-dihydroisoxazole ring for the isoxazole ring not only broadened the antibacterial spectrum but also resulted in a significant increase in antibacterial activity against S. aureus strains. Taken together, these results suggest a promising chemotype for the development of new FtsZ-targeting bactericidal agents.

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.

Method for preparing isoxazoline derivative

The invention discloses a method for preparing an isoxazoline derivative. The method comprises the following steps: by taking an olefin derivative, a diazonium derivative and tert-butyl nitrite as reaction substrates, and a copper compound as a catalyst, in the presence of alkali, coupling metal carbine with a free radical, and further performing serial cyclization reaction, thereby obtaining the isoxazoline derivative. The invention designs a method for very conveniently synthesizing the isoxazoline derivative from cheap and easily obtained raw materials with a cheap metal copper compound as a catalyst in a sealed tube system directly under gentle reaction conditions. By adopting the method, the problems that in a conventional synthesis method, a great amount of oxidants are used, precious metals are adopted as catalysts and harsh experiment conditions such as anhydrous and anaerobic reaction are implemented are avoided, the reaction is simple and feasible, later treatment is simple, and potential industrial application values can be achieved.

Coupling Reaction of Cu-Based Carbene and Nitroso Radical: A Tandem Reaction to Construct Isoxazolines

In this letter, an unprecedented cross-coupling reaction between copper carbene and nitroso radical has been developed. This radical-carbene coupling reaction (RCC reaction) offers a novel approach for the preparation of various isoxazolines, which features the construction of C-C, C-O, and C=N bonds in a one-pot process. The synthetic utility of our method is further enhanced by its mild reaction conditions, wide substrate scope, and simple procedures.

Reaction of esters of 2-arylcyclo-propanecarboxylic acids with nitrous acid. Synthesis of aryl-substituted 3-ethoxycarbonyl-4,5-dihydroisoxazoles and 3-ethoxycarbonylisoxazoles

Esters of 2-arylcyclopropanecarboxylic acids react with nitrous acid generated in situ with regioselective insertion of the nitrosyl cation into the cyclopropane ring. Depending on the substrate/nitrosylating agent ratio, the reaction proceeds with the formation of either aryl-substituted 3-ethoxycarbonyl-4,5-dihydroisoxazoles or the corresponding isoxazoles. The nature and position of the substituents in the aromatic ring of the starting 2-arylcyclopropanecarboxylic acid esters affect the reaction rate but have no effect on the regioselectivity of the attack by the nitrosyl cation on the three-membered ring. A dependence of the reactivity of isomeric substrates on their stereochemistry and position of the nitro group in the aromatic ring is noted for 2- and 4-nitrophenyl derivatives of esters of cis- and trans-2-arylcyclopropanecarboxylic acids.