829-31-2

Usage

Chemical compound

3-(4-Chlorophenyl)-1,2,3-oxadiazole-3-ium-5-olate
Salt of oxadiazole-3-ium-5-olate anion and 4-chlorophenyl cation
Crystalline form
Potential applications in pharmaceuticals and agrochemicals
Building block in organic synthesis
Potential biological activities
Promising candidate for further research and development in chemistry and medicine

InChI:InChI=1/C8H5ClN2O2/c9-6-1-3-7(4-2-6)11-5-8(12)13-10-11/h1-5H/p+1

Upstream product

• 108-24-7 acetic anhydride 
• 13728-11-5 N-(4-chlorophenyl)-N-nitrosoglycine 
• 5465-90-7 N-(4-chlorophenyl)glycine 
• 2521-89-3 ethyl 2-((4-chlorophenyl)amino)acetate 
• 106-47-8 4-chloro-aniline 

Downstream Products

• 4918-25-6 4-bromo-3-(4-chloro-phenyl)-sydnone 
• 5585-15-9 3-(4-chloro-phenyl)-4-nitro-sydnone 
• 86870-34-0 3-(4-chloro-phenyl)-4-formyl-sydnone 
• 76242-32-5 4-acetyl-3-(4-chlorophenyl)sydnone 
• 54624-69-0 dimethyl 1-(4-chlorophenyl)-1H-pyrazole-3,4-dicarboxylate 
• 190731-01-2 (E)-(η(5)-C5Me5)(CO)2FeP=CHN(4-ClC6H4)N=C(NMe2)2 
• 1225057-57-7 3-(4-chlorophenyl)-4-(2-thiophenyl)sydnone 
• 1225057-58-8 3-(4-chlorophenyl)-4-(2-pyridyl)sydnone 
• 86388-64-9 3,4-bis(4-chlorophenyl)sydnone 
• 1225057-59-9 3-(4-chlorophenyl)-4-(phenylethynyl)sydnone 
• 1225057-55-5 3-(4-chlorophenyl)-4-(4-methoxyphenyl)sydnone 
• 61073-53-8 2-(4-chlorophenyl)-2H-indazole 
• 1315168-30-9 C₁₄H₇ClN₂O₂S 
• 1315168-32-1 C₁₄H₁₀ClN₃ 

Relevant academic research and scientific papers

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.

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.

Ultrafast Click Chemistry with Fluorosydnones

We report the synthesis and reactivity of 4-fluorosydnones, a unique class of mesoionic dipoles displaying exquisite reactivity towards both copper-catalyzed and strain-promoted cycloaddition reactions with alkynes. Synthetic access to these new mesoionic compounds was granted by electrophilic fluorination of σ-sydnone PdIIprecursors in the presence of Selectfluor. Their reactions with terminal and cyclic alkynes were found to proceed very rapidly and selectively, affording 5-fluoro-1,4-pyrazoles with bimolecular rate constants up to 104m?1s?1, surpassing those documented in the literature with cycloalkynes. Kinetic studies were carried out to unravel the mechanism of the reaction, and the value of 4-fluorosydnones was further highlighted by successful radiolabeling with [18F]Selectfluor.

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 of 2H-indazoles by the [3 + 2] cycloaddition of arynes and sydnones

A rapid and efficient synthesis of 2H-indazoles has been developed, which involves the [3 + 2] dipolar cycloaddition of arynes and sydnones. The process proceeds under mild reaction conditions in good to excellent yields.

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.

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.

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.

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