31767-13-2

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 67-56-1 methanol 
• 3545-80-0 hydroxyiminoacetic acid 
• 81539-54-0 isonitroso Meldrum’s acid 
• 922-68-9 Methyl glyoxylate 
• 109745-70-2 methyl glyoxylate methyl hemi-acetal 
• 463-51-4 Ketene 

Downstream Products

• 107046-74-2 Cyclohexyl-[(E)-hydroxyimino]-acetic acid methyl ester 
• 178240-01-2 methyl (E)-2-hydroxyimino-2-o-tolylacetate 

Relevant academic research and scientific papers

Acid-catalyzed aza-Diels-Alder versus 1,3-dipolar cycloadditions of methyl glyoxylate oxime with cyclopentadiene

The acid-catalyzed 1,4- and 1,3-cycloadditions between methyl glyoxylate oxime (1) and cyclopentadiene were investigated using various Lewis and/or Bronsted acids at different temperatures in dichloromethane as solvent. Besides the expected new adducts, (±)-methyl [(3-exo)-2-hydroxy-2-azabicyclo[2.2.1]hept-5-ene]-3-carboxylate (2) and (±)-methyl [(3-endo)-2-hydroxy-2-azabicyclo[2.2.1]hept-5-ene]-3-carboxylate (3), a third adduct, (±)-methyl (1R,4R,5R)-(2-oxa-3-azabicyclo[3.3.0]oct-7-ene)-4-carboxylate (4), whose formation can be explained by a 1,3-dipolar cycloaddition, was obtained. Yields and product ratios were found to be more dependent on the catalyst than on the temperature; these results and the stereochemistry of the adducts, confirmed by spectroscopic data (1H and 13C NMR) and by X-ray crystallography, were used to analyze and propose a mechanistic explanation for both cycloadditions.

Indium mediated allylation of glyoxylate oxime ethers, esters and cyanoformates

An indium mediated procedure has been developed for the allylation of activated O-functionalised oximes and nitriles as exemplified by a variety of glyoxylate derivatives. This method gives the corresponding free (or protected) amine in a one pot-process. The method is regiospecific and is carried out under remarkably mild conditions so that even oxime esters can be subjected to the typical reaction conditions.

Process for the preparation of phenyl glyoxylic acid ester oximes

The invention relates to a process for the preparation of compounds of formula (I) wherein: R1is optionally substituted alkyl, R2is C1-C6alkyl, C3-C6cycloalkyl, C3-C6cycloalkyl-C1-C2alkyl, aryl, aryl-C1-C2alkyl, heterocyclyl, heterocycly-C1-C2alkyl, which groups are optionally substituted by alkyl, alkoxy, or halogen; in which process (I) an aniline of formula (II), is diazotized with an organic or inorganic nitrite or nitrous acid; (2) the resulting diazonium salt is reacted with an oxime of formula (III) in presence of a copper(II)-salt.

Synthesis of nucleosides and related compounds. XXXIV. Synthesis of 5- Isonitroso-1,3-dioxane-4,6-diones and their reactions

Synthesis of 5-isonitroso-1,3-dioxane-4,6-dione (2: isonitroso Meldrum's acid) and related compounds and their reactions were described. Compound (2) reacted with various alcohols to give hydroxyiminoacetic acid esters in moderate yields. Compound 2 was a

SYNTHESES AND FLASH VACUUM PYROLYSES OF HIGHLY FUNCTIONALIZED α-N-HYDROXY AMINO ACIDS

Flash vacuum pyrolisis (FVP) of N-acetoxy-N-vinylacetylmethionine sulfoxide and N-acetyl-N-hexadienoylglycine produced dihydropyridones, presumably by cycloaddition reactions of intermediate imines.

Substituted phenylphosphinyloxy- and phosphinylthio-iminocarboxylates useful for the control of weeds

Novel substituted phenylphosphinyloxy- and phenylphosphinylthio-iminocarboxylates, synthesis thereof, intermediates therefor, and the use of said novel compounds for the control of weeds.