99876-44-5Relevant academic research and scientific papers
Structure and Reactivity of Highly Twisted N-Acylimidazoles
Stone, Elizabeth A.,Mercado, Brandon Q.,Miller, Scott J.
, p. 2346 - 2351 (2019)
A modular and efficient synthesis of highly twisted N-acylimidazoles is reported. These twist amides were characterized via X-ray crystallography, NMR spectroscopy, IR spectroscopy, and DFT calculations. Modification of the substituent proximal to the amide revealed a maximum torsional angle of 88.6° in the solid state, which may be the most twisted amide reported for a nonbicyclic system to date. Reactivity and stability studies indicate that these twisted N-acylimidazoles may be valuable, namely as acyl transfer reagents.
Reactivite du nucleophile azoture vis-a-vis de cations heterocycliques aromatiques. VIII. Rearrangement de β-tetrazolo-trans-benzalacetophenones
Cherton, Jean-Claude,Bazinet, Marc,Bolze, Marie-Madeleine,Lanson, Marc,Desbene, Paul-Louis
, p. 2601 - 2607 (2007/10/02)
β-Tetrazolyl-trans-benzalacetophenones (T) isomerize upon heating into the corresponding azido-azomethines (A).These non-isolable products undergo various transformations depending on the reaction conditions.With organic bases such as triphenylphosphine or pyridine, their interception can occur.In aromatic solvents, a rearrangement involving loss of nitrogen leads to five-membered diazoted heterocycles: N-benzoyl imidazoles and pyrazoles, via intermediate diazirines and oxazepines.Protic solvents have been found to facilitate the isomerisation of tetrazoles into azidoazomethines.Solvolysis of the azidooxazine and in some cases of the oxazinium species resulting from the equilibrium and reaction: are then observed.
