79289-47-7Relevant academic research and scientific papers
Facile Preparations of 1,4-(Diphenylmethyleneamino)piperazine-2,5-diones and N-Phenylmethyleneamino-β, γ, and δ-lactams from Benzylidene Hydrazines and α, β, γ and δ-Haloacyl Halides
Okawara, Tadashi,Kato, Rie,Furukawa, Mitsuru
, p. 2426 - 2429 (2007/10/02)
The reaction of benzylidene hydrazines (1) with various haloacyl halides (2) was carried out in aqueous NaOH-CH2Cl2 in the presence of a phase transfer catalyst to afford 1,4-(diphenylmethyleneamino)piperazine-2,5-diones (3) and N-phenylmethyleneamino-β,
Synthesis and properties of 3-oxo-1,2-diazetidinium ylides
Taylor, Edward C.,Haley, Neil F.,Clemens, Robert J.
, p. 7743 - 7752 (2007/12/18)
Treatment of α-chloroacylhydrazones of diaryl and certain aralkyl and dialkyl ketones with sodium hydride in anhydrous tetrahydrofuran gives 1-(disubstituted methylene)-3-oxo-1,2-diazetidinium inner salts (ylides). The reaction pathway involves formation of the hydrazone anion followed by intramolecular SN2 halide displacement (with complete inversion at the α carbon) by the sp2 imine nitrogen. These 1-(disubstituted methylene)-3-oxo-1,2-diazetidinium ylides are reduced by sodium borohydride to give 1-substituted 1,2-diazetidin-3-ones, undergo dipolar cycloaddition reactions to give fused aza-β-lactams, and can be hydrolyzed with p-toluenesulfonic acid monohydrate to the p-toluenesulfonic acid salt of 1,2-diazetidinone.
