1285526-84-2

Upstream product

• 102588-18-1 O-(trimethylsilyl)-N-((trimethylsilyl)oxy)-N-vinylhydroxylamine 
• 65-85-0 benzoic acid 
• 1285526-77-3 C₁₈H₁₈N₂O₆ 
• 7127-19-7 2-phenyl-1,3-oxazoline 

Relevant academic research and scientific papers

Addition of HO-Acids to N,N-Bis(oxy)enamines: Mechanism, Scope and Application to the Synthesis of Pharmaceuticals

The regioselectivity of the addition of HO-acids to the activated π bond in N,N-bis(oxy)enamines has been found to be dramatically dependent upon the solvent. Mechanistic investigations and quantum-chemical calculations revealed that solvent affects the reaction pathway. In basic solvents (DMF, NMP, DMSO), N,N-bis(oxy)enamines were converted into nitrosoalkenes by a Lewis base promoted process followed by oxy-Michael addition of the HO-acid. In non-polar solvents (toluene, CH2Cl2), the reaction occurs by an acid-promoted SN′ substitution of the N-oxy-group via a highly reactive N-vinyl-N-alkoxynitrenium species. Based on these studies, general and efficient protocols for the oximinoalkylation of various HO-acids (carboxylic acids, phenols, hydroxamic, phosphoric and sulfonic acids) employing readily available N,N-bis(oxy)enamines were developed. These methods proved to be applicable to the post-modification of natural molecules bearing acidic OH groups (such as steroidal hormones, bile acids, protected amino acids and peptides) and ligands (BINOL). The resulting α-oxyoximes were demonstrated to be useful precursors of valuable 1,2-amino alcohol or 1,2-hydroxylamino alcohol derivatives, including the antiarrhythmic drug Mexiletine and a potent matrix metalloproteinase inhibitor.

Azodioxy-carbonyl compounds by oxidation of cyclic imines with m-CPBA

This article reports a simple and efficient synthesis of C-nitroso compounds (azodioxy esters or ketones and oximes) through a double oxidation of cyclic imines (4,5-dihydrooxazoles and 3,4-dihydro-2H-pyrroles) with m-CPBA. C-Nitroso derivatives seem to b