215536-63-3Relevant academic research and scientific papers
Mannich type reactions of acylhydrazones with silyl enolates for the synthesis of β-amino ester, β-amino ketone, β-lactam, pyrazolidinone, and pyrazolone derivatives
Okitsu, Osamu,Oyamada, Hidekazu,Furuta, Takayuki,Kobayashi, Shu
, p. 1143 - 1162 (2000)
In the presence of a catalytic amount of a rare earth triflate, acylhydrazones reacted with silyl enolates to afford the corresponding β-N'- acylhydrazino esters in high yields. A three-component reaction of an aldehyde, an acylhydrazine, and a silyl enolate was also performed successfully. The hydrazino esters thus obtained were readily converted to β-amino ester, β-amino ketone, β-lactam, pyrazolidinone, and pyrazolinone derivatives.
Use of acylhydrazones as electrophiles in Mannich-type reactions, β-lactam, pyrazolidinone, and pyrazolone synthesis
Kobayashi, Shu,Furuta, Takayuki,Sugita, Kasumi,Oyamada, Hidekazu
, p. 1019 - 1021 (2007/10/03)
In the presence of a catalytic amount of scandium triflate [Sc(OTf)3], 4-trifluoromethylbenzoylhydrazones reacted with silyl enolates to afford the corresponding adducts, β-N'-acylhydrazinocarbonyl compounds, in high yields. Reductive cleavage of the nitrogen-nitrogen bond of the hydrazino compounds was performed using Raney Ni under H2 atmosphere, to give β-aminocarbonyl compounds. The two-step process is regarded as a novel Mannich-type reaction using acylhydrazones as electrophiles. Moreover, the hydrazino compounds were also successfully converted to β-lactam, pyrazolidinone, and pyrazolone derivatives.
