6415-68-5

Usage

InChI:InChI=1/C8H8N2O3/c11-8(12)6-10(9-13)7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12)

Upstream product

• 103-01-5 N-Phenylglycine 
• 2216-92-4 N-phenylglycine ethyl ester 
• 62-53-3 aniline 
• 7664-93-9 sulfuric acid 
• 79-11-8 chloroacetic acid 

Downstream Products

• 14606-16-7 3-(4-bromophenyl)-5-methyl-1,3,4-oxadiazol-2(3H)-one 
• 50270-60-5 ethyl 1-phenylhydrazinoacetic acid 
• 4408-70-2 (N-phenyl-hydrazino)-acetic acid 
• 508191-77-3 3-phenylsydnone 
• 91-78-1 1,3,5-triphenylhexahydro-1,3,5-triazine 
• 13973-33-6 4-acetyl-3-phenylsydnone 
• 614-00-6 N-methyl-N-nitrosoaniline 
• 124-38-9 carbon dioxide 
• 1394248-97-5 1-piperidinomethyl-3-[1-(4-isobutylphenyl)ethyl]-4-(3-phenyl-4-sydnonylidene)amino-1,2,4-triazol-5-thione 
• 1394248-99-7 1-N-ethyl-piperazinomethyl-3-[1-(4-isobutylphenyl)ethyl]-4-(3-phenyl-4-sydnonylidene)amino-1,2,4-triazol-5-thione 
• 14484-83-4 4-formyl-3-phenyl-sydnone 
• 3815-83-6 3,4-diphenylsydnone 
• 1396123-83-3 3-phenyl-4-(trifluoromethyl)-1,2,3-λ⁵-oxadiazol-3-ium-5-olate 
• 4918-38-1 4-cyano-3-phenyl-1,2,3-λ⁵-oxadiazol-3-ium-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.

Synthesis and crystal structure of 4-trifluoroacetyl-3-phenylsydnone

4-Trifluoroacetyl-3-phenylsydnone was first synthesized by trifluoromethylation of 4-formyl-3-phenylsydnone followed by oxidation of the corresponding trifluoromethyl alcohol. The structure of the product was determined by single-crystal X-ray analysis.

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.

1,3-Dipolar cycloaddition between acetylenic dipolarophiles and sydnone-N-ylides as bis(1,3-dipoles)

1,3-Dipolar cycloaddition reaction of sydnone-N-ylides, as model bis(1,3-dipoles), with acetylenic dipolarophiles in 1,2-epoxybutane under reflux gave exclusively pyrroloazines containing a sydnone moiety that resulted by preferred reaction of the N-ylide

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.

Discovery of chemoselective and biocompatible reactions using a high-throughput immunoassay screening

An immunoassay-based method was used to screen numerous combinations of dipoles and dipolarophiles for their ability to undergo chemoselective and biocompatible [3+2] cycloaddition reactions. The approach fulfills most of the requirements of the click concept and led to the discovery of a copper-catalyzed reaction that generates pyrazoles from sydnone and alkyne reagents. Copyright

Regioselective reaction: Synthesis, characterization and pharmacological activity of some new Mannich and Schiff bases containing sydnone

A novel series of 1-substituted aminomethyl-3-[1-(4-isobutylphenyl)ethyl]- 4-(3-aryl-4-sydnonylidene) amino-1,2,4-triazol-5-thiones (9), was prepared from the 3-[1-(4-isobutylphenyl)ethyl]-4-(3-aryl-4-sydnonylidene) amino 5-mercapto-1,2,4-triazoles (8) by aminomethylation with formaldehyde and secondary amine. The structures of Schiff bases (8) and Mannich bases (9) were characterized on the basis of IR, NMR, mass spectra1 data and elemental analysis. The newly synthesized compounds were screened for their anti-inflammatory and analgesic activities. Mannich bases (9) carrying piperidine and morpholine residues showed promising anti-inflammatory and analgesic activity.

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.