106412-77-5

Upstream product

• 551-93-9 2-aminoacetophenone 
• 106776-34-5 3-(2-acetylphenyl)sydnone oxime 
• 78191-00-1 N-Methoxy-N-methylacetamide 
• 508191-77-3 3-phenylsydnone 
• 121163-62-0 C₁₀H₁₀N₂O₄ 
• 106412-72-0 4-Bromo-3-(2-acetylphenyl)-sydnone 

Downstream Products

• 106776-39-0 3-(2-acetylphenyl)sydnone oxime-O-(p-toluenesulfonate) 
• 106776-38-9 3-(2-acetylphenyl)sydnone oxime-O-benzenesulfonate 
• 106776-37-8 3-(2-acetylphenyl)sydnone oxime-O-methanesulfonate 
• 104273-21-4 3-(2-acetamidophenyl)sydnone 
• 106776-34-5 3-(2-acetylphenyl)sydnone oxime 
• 106412-72-0 4-Bromo-3-(2-acetylphenyl)-sydnone 
• 144729-24-8 3-<2-<1-<1-<<2-(Sydnon-3-yl)phenyl>ethylidene>hydrazono>ethyl>phenyl>sydnone 

Relevant academic research and scientific papers

The sydnone ring as an ortho-director of lithiation. 2. Dilithiation of 3-phenylsydnone and regiospecific @?o-aryl acylation using N-methoxy-N-methylamides

Readily available 3-phenylsydnone (1) reacts with n-butyllithium/TMEDA to form the dilithio species 2 which can be regiospecifically acylated at the ortho-aryl position using N-methoxy-N-methylamides (Weinreb's amides).

DEBROMINATION OF 4-BROMO-3-ARYLSYDNONES WITH SODIUM SULFITE

4-Bromo-3-arylsydnones 1 are debrominated to the corresponding 3-arylsydnones 2 in good to excellent yield using sodium sulfite in methanol/water.In contrast to previously employed reagents, the reaction is successful in the presence of electron-donating,

The Efficient Synthesis of 3-Arylsydnones Under Neutral Conditions

Various substituted aryl sydnones can be prepared in high yield under mild, neutral conditions by nitrosation of the appropriate aryl glycine with isoamyl nitrite in dimethoxyethane followed by cyclization with trifluoroacetic anhydride.

Acid Induced Reactions of a Sydnone Ketoxime

3-(2-Acetylphenyl)sydnone oxime 1a reacts with acids (methanesulfonic-, p-toluenesulfonic, trifluoroacetic acid or Amberlite IR 118) to give products apparently derived from protonation of the oxime oxygen or nitrogen atom followed by cyclization to the sydnone ring or interception by water.

DEBROMINATION OF 4-BROMO-3-ARYLSYDNONES WITH SODIUM DITHIONITE.

A variety of 4-bromo-3-arylsydnones can be debrominated with sodium dithionite in excellent yield under very mild conditions.

Synthesis and Reactions of Sydnone Oximes

Oximino sydnones 1a,b have been prepared and subjected to reaction with a variety of electrophilic reagents.The aldoxime reacted with all of the latter (except acetic anhydride) to give 3-(2-cyanophenyl)sydnone 1h.With acetic anhydride, both sydnone oximes formed the corresponding O-acetates 1i,m.Similarly, O-sulfonates 1l,k,j, respectively, were obtained by reaction of the ketoxime with benzene-, methane- and para-toluenesulfonyl chloride.Thermolysis (on silica) of the O-sulfonates and the O-acetates has been examined.