6299-51-0

Usage

InChI:InChI=1/C8H5N3O4/c12-8-5-10(9-15-8)6-1-3-7(4-2-6)11(13)14/h1-5H/p+1

Upstream product

• 134863-55-1 4-acetyl-3-(4-nitrophenyl)sydnone 
• 100-01-6 4-nitro-aniline 
• 350-46-9 4-Fluoronitrobenzene 
• 69978-02-5 N-(4-nitro-phenyl)-N-nitroso-glycine 

Downstream Products

• 892962-82-2 1-(4-nitrophenyl)-1H-pyrazole-3,4-dicarbohydrazide 
• 892962-88-8 1-(4-nitrophenyl)-N₃',N₄'-dibenzoyl-1H-pyrazole-3,4-dicarbohydrazide 
• 1002334-22-6 1-(4-nitrophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trimethylsilyl)-1H-pyrazole 
• 1002334-23-7 1-(4-nitrophenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trimethylsilyl)-1H-pyrazole 
• 13788-77-7 1-(4-nitrophenyl)-3-phenyl-1H-pyrazole 
• 894423-32-6 C₉H₉N₅O₃ 
• 1449770-55-1 2-(4-nitrophenyl)-5-methyl-4-(1H-tetrazol-1-yl)-2H-1,2,4-triazol-3(4H)-one 
• 27182-39-4 5-methyl-3-(4-nitro-phenyl)-3H-[1,3,4]oxadiazol-2-one 
• 134863-55-1 4-acetyl-3-(4-nitrophenyl)sydnone 
• 23875-85-6 dimethyl 1-(4-nitrophenyl)-1H-pyrazole-3,4-dicarboxylate 
• 636-99-7 4-nitrophenylhydrazine hydrochloride 
• 110177-91-8 3-(4-acetylamino-phenyl)-sydnone 
• 17105-35-0 3-(4-aminophenyl)sydnone 
• 14606-04-3 4-bromo-3-(4-nitrophenyl)-1,2,3λ⁵-oxadiazol-3-ylium-5-olate 

Relevant academic research and scientific papers

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.

Discovery of Fluorogenic Diarylsydnone-Alkene Photoligation: Conversion of ortho-Dual-Twisted Diarylsydnones into Planar Pyrazolines

A small library of diarylsydnones (DASyds) was constructed based on aryl-pairing combinations and subjected to click reaction toward alkenes under photoirradiation with high efficiency. We were able to demonstrate the utility of DASyds for highly fluorescent turn-on ligation targeting the trans-cyclooct-4-en-1-ol moieties on protein.

4-Halogeno-sydnones for fast strain promoted cycloaddition with bicyclo-[6.1.0]-nonyne

New sydnone derivatives have been synthesized and screened for their capacity to undergo fast copper-free cycloaddition reaction with bicyclo-[6.1.0]-nonyne. The influences of substitution in positions N-3 and C-4 of sydnones have been particularly studied leading to the identification of highly reactive partners for bio-orthogonal ligation reactions.

One-pot synthesis of 1,4-disubstituted pyrazoles from arylglycines via copper-catalyzed sydnone-alkyne cycloaddition reaction

A robust method for constructing 1,4-pyrazoles from arylglycines was developed using the copper-catalyzed sydnone-alkyne cycloaddition reaction. The procedure offers a straightforward and general route to the pyrazole heterocycle through a three-step one-pot procedure.

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.

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.

Reactions of 4-acetylsydnones with hydrazine: Formation of 2,4- dihydropyrol-3-ones

Reactions of 4-acetylsydnones with hydrazine at room temperature yielded a series of 2,4-dihydropyrazol-3-ones. The cycloaddition via sydnone rings with loss of a nitrogen oxide ion is a new type of reaction for the application of sydnone in organic synth