1014-23-9

Usage

Uses

Used in Organic Synthesis:
5-(4-Nitrophenyl)-1,3-oxazole is utilized as a building block in organic synthesis for the preparation of a range of pharmaceuticals, agrochemicals, and materials. Its unique structure and reactivity make it a valuable component in the creation of diverse chemical entities.
Used in Research and Development:
In the realm of research and development, 5-(4-Nitrophenyl)-1,3-oxazole serves as a precursor for the synthesis of other complex molecules with specific properties and applications. Its ability to be modified and incorporated into larger structures allows scientists to explore new avenues in chemical and material science.
Used in Pharmaceutical Industry:
5-(4-Nitrophenyl)-1,3-oxazole is used as a key intermediate in the pharmaceutical industry for the development of new drugs. Its incorporation into drug molecules can potentially enhance their efficacy, selectivity, or other pharmacological properties.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, 5-(4-NITROPHENYL)-1,3-OXAZOLE is employed as an intermediate in the synthesis of pesticides and other agrochemical products, where its reactive nature can be harnessed to create molecules with specific pesticidal or herbicidal activities.
Safety Precautions:
Due to the potential toxicity associated with 5-(4-Nitrophenyl)-1,3-oxazole, it is crucial to follow proper handling and safety protocols when working with 5-(4-NITROPHENYL)-1,3-OXAZOLE. This includes the use of appropriate personal protective equipment, working in well-ventilated areas, and adhering to guidelines for the safe disposal of chemical waste.

InChI:InChI=1/C9H6N2O3/c12-11(13)8-3-1-7(2-4-8)9-5-10-6-14-9/h1-6H

Upstream product

• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 555-16-8 4-nitrobenzaldehdye 
• 29166-72-1 N,N,N′,N′-tetramethyl-N″-tert-butylguanidine 
• 2929-91-1 4-nitrobenzylidene diacetate 
• 150619-47-9 N-methylene-1-(p-tolylsulfonyl)methylamine 
• 785-80-8 p-nitrobenzylideneaniline 
• 10564-55-3 1-isocyanatomethanesulfonyl-4-methyl-benzene 
• 95-54-5 1,2-diamino-benzene 
• 37118-22-2 (4S,5S)-5-(4-Nitro-phenyl)-4-(toluene-4-sulfonyl)-4,5-dihydro-oxazole 
• 288-42-6 oxazol 
• 586-78-7 para-nitrophenyl bromide 
• 14922-36-2 4-nitrophenylglyoxylic acid 
• 619-73-8 4-nitrobenzyl chloride 
• 100-11-8 1-bromomethyl-4-nitro-benzene 

Downstream Products

• 1008-95-3 4-(oxazol-5-yl)aniline 
• 1059544-48-7 5-(4-nitrophenyl)-2-styryl-oxazole 
• 1206483-04-6 5-(4-nitro-phenyl)-2-phenylethynyl-oxazole 
• 76046-02-1 C₁₆H₁₂N₂O₃ 
• 1239719-78-8 C₁₀H₈N₂O₄ 
• 1226890-24-9 5-(4-nitrophenyl)-2-[(triisopropylsilyl)ethynyl]oxazole 
• 21304-53-0 5-(4-nitrophenyl)-2-phenyloxazole 
• 4271-09-4 2,2'-benzothiazolyl 
• 1395680-38-2 2-(5-(4-nitrophenyl)oxazol-2-yl)benzothiazole 
• 1402228-08-3 5-(4-nitrophenyl)-2-{1-(pyrimidin-2-yl)-1H-indol-2-yl}oxazole 
• 1309868-12-9 2-(benzofuran-2-yl)-5-(4-nitrophenyl)-oxazole 

Relevant academic research and scientific papers

Cu-Catalyzed Oxidative-Reaction of Tosylmethylisocyanide and Benzyl Alcohols: Efficient Synthesis of 4-(tert-butylperoxy)-5-aryloxazol-2(3H)-ones and 5-Aryloxazol-2(5H)-ones

Herein, a novel copper-catalyzed reaction of tosylmethylisocyanide (TosMIC) with benzyl alcohols has been developed using tert-butyl hydroperoxide (TBHP) for the first time. The reaction involves the in-situ oxidation of benzyl alcohol to corresponding be

A new efficient synthesis of 5-aryloxazoles from arylidene diacetates and application to the preparation of BMS-337197, a novel IMPDH inhibitor

A new method for the synthesis of 5-aryloxazoles is described. Treatment of arylidene diacetates with one equivalent of TosMIC reagent in the presence of excess of potassium carbonate in methanol afforded 5-aryloxazoles in "one-pot" in 90-94%. Heteroaryli

Discovery of a Potent Glutathione Peroxidase 4 Inhibitor as a Selective Ferroptosis Inducer

Potent and selective ferroptosis regulators promote an intensive understanding of the regulation and mechanisms underlying ferroptosis, which is highly associated with various diseases. In this study, through a stepwise structure optimization, a potent and selective ferroptosis inducer was developed targeting to inhibit glutathione peroxidase 4 (GPX4), and the structure-activity relationship (SAR) of these compounds was uncovered. Compound26aexhibited outstanding GPX4 inhibitory activity with a percent inhibition up to 71.7% at 1.0 μM compared to 45.9% of RSL-3. At the cellular level,26acould significantly induce lipid peroxide (LPO) increase and effectively induce ferroptosis with satisfactory selectivity (the value of 31.5). The morphological analysis confirmed the ferroptosis induced by26a. Furthermore,26asignificantly restrained tumor growth in a mouse 4T1 xenograft model without obvious toxicity.

Design, synthesis and biological evaluation of imidazole and oxazole fragments as HIV-1 integrase-LEDGF/p75 disruptors and inhibitors of microbial pathogens

We describe here the synthesis of libraries of novel 1-subtituted-5-aryl-1H-imidazole, 5-aryl-4-tosyl-4,5-dihydro-1,3-oxazole and 5-aryl-1,3-oxazole fragments via microwave (MW)-assisted cycloaddition of para-toluenesulfonylmethyl isocyanide (TosMIC) to imines and aldehydes. The compounds obtained were biologically evaluated in an AlphaScreen HIV-1 IN-LEDGF/p75 inhibition assay with six imidazole-based compounds (16c, 16f, 17c, 17f, 20a and 20d) displaying more than 50% inhibition at 10 μM, with IC50 values ranging from 7.0 to 30.4 μM. Additionally the hypothesis model developed predicts all active scaffolds except 20d to occupy similar areas as the N-heterocyclic (A) moiety and two aromatic rings (B and C) of previously identified inhibitor 5. These results indicate that the identified compounds represent a viable starting point for their use as templates in the design of next generation inhibitors targeting the HIV-1 IN and LEDGF/p75 protein-protein interaction. In addition, the in vitro antimicrobial properties of these fragments were tested by minimum inhibitory concentration (MIC) assays showing that compound 16f exhibited a MIC value of 15.6 μg/ml against S. aureus, while 17f displayed a similar MIC value against B. cereus, suggesting that these compounds could be further developed to specifically target those microbial pathogens.

Reaction Conditions for the Regiodivergent Direct Arylations at C2- or C5-Positions of Oxazoles using Phosphine-Free Palladium Catalysts

Two sets of reaction conditions for the regiodivergent C2- or C5- direct arylations of oxazole are reported. In both cases, phosphine-free catalysts and inexpensive bases were employed allowing the access to the arylated oxazoles in moderate to high yields. Using Pd(OAc)2/KOAc as catalyst and base, regioselective C5-arylations were observed; whereas, using Pd(acac)2/Cs2CO3 system, the arylation occurred at the C2-position of oxazole. The higher reactivity of C5-H bond of oxazole as compared to the C2-H bond in the presence of Pd(OAc)2/KOAc system is consistent with a concerted metalation deprotonation mechanism; whereas the C2-arylation likely occurs via a simple base deprotonation of the oxazole C2-position. Then, from these C2- or C5-arylated oxazoles, a second palladium-catalyzed direct C?H bond arylation affords 2,5-diaryloxazoles with two different aryl groups. We also applied these sequential arylations to the straightforward synthesis of 2-arylphenanthro[9,10-d]oxazoles via three C?H bond functionalization steps. The Ru-catalyzed C?H arylation of the aryl unit of 2-aryloxazoles is also described. (Figure presented.).

Tandem oxidative isocyanide-based cycloaddition reactions in the presence of MIL-101(Cr) as a reusable solid catalyst

The tandem oxidative three-component synthesis of two types of the heterocycles such as furans and imidazopyridines, via isocyanides [1+4] cycloaddition reactions in the presence of MIL-101(Cr) under aerobic conditions are reported. When the 4-toluenesulfonylmethyl isocyanide was used, an unexpected [3+2] cycloaddition reaction of isocyanides with aldehydes accomplished and dihydrophenyloxazoles and phenyloxazoles produced. These syntheses were successfully carried out using a wide scope of the substrates.

A One-Pot Tandem Approach for the Synthesis of 5-(Het)aryloxazoles from Substituted (Het)aryl Methyl Alcohols and Benzyl Bromides

A new modified van Leusen strategy has been developed for the synthesis of biologically significant 5-substituted oxazoles by the reaction of (het)aryl methyl alcohols or benzyl bromides as precursors with tosylmethylisocyanide (TosMIC) under basic conditions. This method is efficient, takes place under mild reaction conditions, and is tolerant of various functional groups with high yield.

Tandem cycloaddition-decarboxylation of α-keto acid and isocyanide under oxidant-free conditions towards monosubstituted oxazoles

An efficient method, tandem [3 + 2] cycloaddition-decarboxylation of α-keto acid and isocyanide promoted by copper salt, has been developed. Under oxidant-free conditions, a series monosubstituted oxazoles have been constructed. Different from the traditional application of α-oxo acids as acyl surrogates, the elegant approach herein ingeniously avoids consuming excess oxidants.

Copper-mediated C-H/C-H biaryl coupling of benzoic acid derivatives and 1,3-azoles

Hot couple: A precious-metal-free copper-mediated intermolecular direct biaryl coupling of benzoic acid derivatives and 1,3-azoles has been developed. The key to success is the installation of an amide-based bidentate coordinating group, which is easily removed and transformed into the parent ester groups after the coupling reaction. Kinetic studies indicate that the rate-limiting step is the aromatic C-H bond cleavage of benzoic acid derivatives. Copyright

Copper-mediated dehydrogenative biaryl coupling of naphthylamines and 1,3-azoles

A copper-mediated dehydrogenative biaryl cross-coupling of naphthylamines and 1,3-azoles has been developed. The key to its success is the introduction of N,N-bidentate coordination system based on the picolinamide directing group. The reaction proceeds s