26537-61-1

Usage

Uses

Used in Organic Synthesis:
3-(4-bromophenyl)-5-oxo-2,5-dihydro-1,2,3-oxadiazol-3-ium is used as a key intermediate in organic synthesis for the preparation of various complex organic molecules. Its oxadiazole ring and bromophenyl group provide opportunities for further functionalization and the creation of new chemical entities with potential applications in different fields.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 3-(4-bromophenyl)-5-oxo-2,5-dihydro-1,2,3-oxadiazol-3-ium is utilized as a building block for the development of novel drug candidates. Its unique structure can be exploited to design molecules with improved pharmacological properties, such as enhanced potency, selectivity, and bioavailability. 3-(4-bromophenyl)-5-oxo-2,5-dihydro-1,2,3-oxadiazol-3-ium's reactivity and biological activity can be further optimized through modifications to its oxadiazole and bromophenyl moieties.
Used in Medicinal Chemistry:
3-(4-bromophenyl)-5-oxo-2,5-dihydro-1,2,3-oxadiazol-3-ium serves as a versatile scaffold in medicinal chemistry for the design and synthesis of bioactive molecules. Its oxadiazole ring can form hydrogen bonds and engage in π-π stacking interactions, which are crucial for molecular recognition and binding to biological targets. The bromophenyl group can also be modified to fine-tune the compound's lipophilicity, metabolic stability, and pharmacokinetic properties, making it an attractive template for drug discovery efforts.
Used in Chemical Research:
3-(4-bromophenyl)-5-oxo-2,5-dihydro-1,2,3-oxadiazol-3-ium is employed as a model compound in chemical research to study the reactivity and properties of oxadiazole-containing compounds. Its synthesis, functionalization, and reactions with other molecules can provide valuable insights into the behavior of similar heterocycles and inform the design of new synthetic routes and strategies.

Upstream product

• 2521-92-8 ethyl 2-((4-bromophenyl)amino)acetate 
• 106-40-1 4-bromo-aniline 
• 13370-62-2 N‐(4-bromophenyl)glycine 

Downstream Products

• 54624-59-8 4-bromo-3-(4-bromo-phenyl)-sydnone 
• 54624-60-1 3-(4-bromo-phenyl)-4-chloro-sydnone 
• 60642-47-9 3,3'-bis-(4-bromo-phenyl)-4,4'-sulfanediyl-bis-sydnone 
• 86870-33-9 4-formyl-3-(4-bromophenyl)sydnone 
• 1638143-77-7 5,5'-(1-(4-bromophenyl)-1H-pyrazole-3,4-diyl)bis(2-phenyl-1,3,4-oxadiazole) 
• 1638143-79-9 5,5'-(1-(3'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)-1H-pyrazole-3,4-diyl)bis(2-phenyl-1,3,4-oxadiazole) 
• 1638143-80-2 5,5'-(1-(3',5'-bis(trifluoromethyl)-[1,1'-biphenyl]-4-yl)-1H-pyrazole-3,4-diyl)bis(2-phenyl-1,3,4-oxadiazole) 
• 1638143-81-3 5,5'-(1-(4'-methoxy-[1,1'-biphenyl]-4-yl)-1H-pyrazole-3,4-diyl)bis(2-phenyl-1,3,4-oxadiazole) 
• 1638143-82-4 5,5'-(1-(4-(thiophen-2-yl)phenyl)-1H-pyrazole-3,4-diyl)bis(2-phenyl-1,3,4-oxadiazole) 
• 1638143-83-5 5,5'-(1-(4-(thiophen-3-yl)phenyl)-1H-pyrazole-3,4-diyl)bis(2-phenyl-1,3,4-oxadiazole) 
• 1638143-84-6 5,5'-(1-(4-(benzo[b]thiophen-2-yl)phenyl)-1H-pyrazole-3,4-diyl)bis(2-phenyl-1,3,4-oxadiazole) 
• 1638143-85-7 5,5'-(1-(4-(dibenzothiophen-4-yl)phenyl)-1H-pyrazole-3,4-diyl)bis(2-phenyl-1,3,4-oxadiazole) 
• 1638143-78-8 5,5'-(1-(4-(dibenzofuran-4-yl)phenyl)-1H-pyrazole-3,4-diyl)bis(2-phenyl-1,3,4-oxadiazole) 
• 912344-96-8 1-(p-bromophenyl)-1H-pyrazole-3,4-dicarbohydrazide 

Relevant academic research and scientific papers

N,N,N′,N′-Tetrabromobenzene-1,3-disolfonamide (TBBDS) as an efficient promoter for one-pot conversion of N-arylglycines to sydnones in the presence of NaNO2/Ac2O under neutral conditions

N,N,N′,N′-Tetrabromobenzene-1,3-disolfonamide (TBBDS)-promoted one-pot conversion of various N-arylglycines to sydnones using a combination of NaNO2 and Ac2O has been achieved efficiently through N-nitrosation followed by cyclization

Exploiting Synergistic Catalysis for an Ambient Temperature Photocycloaddition to Pyrazoles

Sydnone-based cycloaddition reactions are a versatile platform for pyrazole synthesis, however they operate under harsh conditions (high temperature and long reaction times). Herein we report a strategy that addresses this limitation utilizing the synergistic combination of organocatalysis and visible-light photocatalysis. This new approach proceeds under ambient conditions and with excellent levels of regiocontrol. Mechanistic studies suggest that photoactivation of sydnones, rather than enamines, is key to the successful implementation of this process.

Synthesis and evaluation of photo-activatable β-diarylsydnone-L-alanines for fluorogenic photo-click cyclization of peptides

Herein, we design and synthesize a series of photoactivatable β-diarylsydnone-l-alanines (DASAs), which have excellent photo-reactivity with high fluorescence turn-on toward alkenes in a biocompatible environment. The environmental sensing properties of t

Mechanosynthesis of sydnone-containing coordination complexes

N-Phenyl-4-(2-pyridinyl) sydnone was shown to act as a four-electron donor N,O-ligand in unprecedented coordination complexes featuring three different metallic centers (Co, Cu, and Zn). Starting with various anilines, the use of a ball-mill efficiently enabled the synthesis of N-arylglycines, subsequent nitrosylation and cyclization into sydnones, and further metalation.

Novel sydnone derivatives carrying azidomethyl-1,2, 4-oxadiazole unit and their 1,3-dipolar cycloadditions

A series of 1,2,4-oxadiazolymethyl sydnones carrying azido group were synthesized and subjected to react with a variety of alkenic and acetylenic dipolarophilic reagents; N-phenyl maleimide, phenyl vinyl sulfone, and phenyl propiolic acid. All the new products are identified by spectral/physical data including high-resolution mass measurements and X-ray diffraction data.

Synthesis of 2 H-indazoles by the [3 + 2] dipolar cycloaddition of sydnones with arynes

A rapid and efficient synthesis of 2H-indazoles has been developed using a [3 + 2] dipolar cycloaddition of sydnones and arynes. A series of 2H-indazoles have been prepared in good to excellent yields using this protocol, and subsequent Pd-catalyzed coupl

Synthesis and evaluation of phenyl substituted sydnones as potential DPPH-radical scavengers

A series of phenyl substituted sydnones has been synthesized and their radical-scavenging activity has been studied on DPPH free radical. Out of eighteen compounds screened, nine compounds show interesting activity. A mechanism is presented whereby sydnones scavenge DPPH radical through donating H-atom at 4th-position. Its strong radical-scavenging activity mainly arises from 1, 2, 3-oxadiazolium-5-olate ring. Different substituents and their positions on the phenyl ring differently influence DPPH scavenging activity and therefore, may provide clues to design and develop better free-radical scavenging sydnones with multiple activities.

One-pot conversion of N-arylglycines to sydnones efficiently promoted by bis-chlorine-1,4-diazabicyclo[2.2.2]octane complex Cl2-dabco in the presence of NaNO2/Ac2O under neutral condition

Bis-chlorine-1,4-diazabicyclo[2.2.2]octane complex, (Cl2-DABCO), has been found as an active chlorine complex for effective one-pot conversion of various N-arylglycines to sydnones in high yields (85-95%) under mild and neutral condition.

Microwave-assisted synthesis of N-arylglycines: Improvement of sydnone synthesis

Reactions of anilines with ethyl bromoacetate under microwave irradiation have afforded N-arylglycines that are subsequently converted to their N-nitroso derivatives with a combination of silica chloride or periodic acid, wet SiO2 and sodium nitrite in CH2Cl2 with satisfactory yields. In the final step, the use of 1,3-dibromo-5,5-dimethylhydantoin (DBH) as a new and effective reagent for dehydration of N-nitroso-N-arylglycines to sydnones was successfully examined.

Catalytic activity of 1,3-dibromo-5,5-dimethylhydantoin (DBH) in the one-pot transformation of N-arylglycines to N-arylsydnones in the presence of NaNO2/Ac2O under neutral conditions: Subsequent bromination of these sydnones to their

1,3-Dibromo-5,5-dimethylhydantoin (DBH) has been found to efficiently catalyze the one-pot conversion of various N-arylglycines through N-nitrosation and cyclization to sydnones in combination with NaNO2 and Ac 2O in high yields (80-