3815-80-3

Usage

InChI:InChI=1/C9H8N2O3/c1-13-8-4-2-7(3-5-8)11-6-9(12)14-10-11/h2-6H,1H3

Upstream product

• 52827-01-7 2-((4-methoxyphenyl)(nitroso)amino)acetic acid 
• 147749-35-7 2-(4-methoxyphenylamino)acetic acid methyl ester 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 1194-02-1 4-fluorobenzonitrile 
• 104-94-9 4-methoxy-aniline 
• 50845-77-7 N-(4-methoxy)phenylglycine ethyl ester 
• 22094-69-5 N-(4-methoxyphenyl)glycine 

Downstream Products

• 14484-84-5 3-(4-methoxyphenyl)-4-formylsydnone 
• 34356-36-0 4-acetyl-3-(4-methoxyphenyl)sydnone 
• 37440-89-4 9,10-diaza-10-(4-methoxyphenyl)tetracyclo<6.3.0.0.^4,110.^5,9>undecane 
• 76242-50-7 C₁₈H₁₄N₄O₃S 
• 76242-52-9 C₁₉H₁₆N₄O₃S 
• 76242-51-8 C₁₈H₁₃ClN₄O₃S 
• 76242-53-0 C₁₉H₁₆N₄O₄S 
• 76242-49-4 C₁₂H₁₀N₄O₃S 
• 1002334-20-4 1-(4-methoxyphenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trimethylsilyl)-1H-pyrazole 
• 1002334-21-5 1-(4-methoxyphenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trimethylsilyl)-1H-pyrazole 
• 54624-72-5 dimethyl 1-(4-methoxyphenyl)-1H-pyrazole-3,4-dicarboxylate 
• 1203704-00-0 1-(4-methoxyphenyl)-4-phenyl-1H-pyrazole 
• 63637-59-2 1-(4-methoxyphenyl)-3-phenyl-1H-pyrazole 
• 1335106-48-3 4-[1-oxo-3-(2-hydroxy-3-quinolinyl)-2-propenyl]-3-(4-methoxyphenyl)sydnone 

Relevant academic research and scientific papers

Water-Involved Ring-Opening of 4-Phenyl-1,2,4-triazoline-3,5-dione for “Photo-Clicked” Access to Carbamoyl Formazan Photoswitches In Situ

Cyclic azodicarbonyl derivatives, particularly 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), commonly serve as arenophile, dienophile, enophile and electrophile. Perplexed by its instability in aqueous environment, there are few studies focused on the transient intermediate produced by hydrolysis of PTAD to achieve synthetic significance. Herein, we describe a “photo-click” method that involves nitrile imine (NI) from diarylsydnone to capture the diazenecarbonyl-phenyl-carbamic acid (DACPA) generated by water-promoted ring-opening of PTAD. DFT calculation reveal that H-bonding interactions between PTAD and water are vital to form DACPA which exhibited an umpolung effect during ligation by nature bond orbit (NBO) analysis. The ultra-fast ligation resulted in carbamoyl formazans, as a unique Z?E photo-switchable linker on target molecules, including peptide and drugs, with excellent anti-fatigue performance. This strategy is showcased to construct highly functionalized carbamoyl formazans in situ for photo-pharmacology and material studies, which also expands the chemistry of PTAD in aqueous media.

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.

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.

Sydnone Reporters for Highly Fluorogenic Copper-Free Click Ligations

Bioorthogonal fluorescent turn-on reactions are attractive for the sensitive real-time detection of a variety of phenomena including bioconjugation, chemical reactivity, and material assembly. Herein we describe the use of 3,4-disubstituted sydnones, a singular class of mesoionic dipoles, for highly fluorescent turn-on copper-free click cycloadditions with the fluorogenic dibenzocyclooctyne Fl-DIBO. Coherent with time-dependent density functional theory calculations, the pyrazole cycloadducts were found to be highly fluorescent with compelling photophysical properties including excellent fluorescence enhancement (up to 240-fold), high quantum yields (over 45%), and large Stokes shift (over 100 nm). Furthermore, the good stability and reactivity of 4-chlorosydnones with Fl-DIBO allowed us to employ them as chemical reporters for the challenging detection of modified-proteins in complex cellular extracts, with exquisite specificity in no-wash conditions. This novel fluorogenic system significantly expands our chemical biology toolbox and should be beneficial in countless applications.

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.

Expanding available pyrazole substitution patterns by sydnone cycloaddition reactions

We report the use of alkynylsilanes for the regiocontrolled synthesis of pyrazoles from functionalised sydnones. The strategies outlined herein allow a range of pyrazoles to be accessed with substitution patterns that are otherwise not directly obtained with high selectivity by alkyne cycloadditions. Moreover, this study serendipitously highlighted a simple and convenient procedure for the synthesis of aryl monofluoromethyl ethers through the combination of TBAF and dichloromethane.

Synthesis of aminopyrazoles from sydnones and ynamides

Aminopyrazoles are prepared from readily accessible sydnones and sulfonyl ynamides using either a copper-mediated sydnone alkyne cycloaddition (CuSAC) or in situ generated strained cyclic ynamides.