1000022-07-0Relevant academic research and scientific papers
Dearomatizing anionic cyclization of N-alkyl-N-benzyl(dinaphthyl) phosphinamides. A facile route to γ-(amino)dihydronaphthalenylphosphinic acids
Ruiz-Gomez, Gloria,Iglesias, Maria Jose,Serrano-Ruiz, Manuel,Lopez-Ortiz, Fernando
, p. 9704 - 9712 (2008/03/17)
(Chemical Equation Presented) The dearomatizing anionic cyclization of N-alkyl-N-benzyldi(n-naphthyl)phosphinamides (n = 1, 2) and subsequent trapping with a series of electrophiles (MeOH, MeI, CF3SO3Me, Me3O+BF4-, AllylBr, and PhCH 2Br) have been accomplished. Optimized reaction conditions (base, temperature, reaction time) allow for synthesizing tetrahydro-1H-naphtho[1,2-c] [1,2]-azaphosphole 1-oxides 13 and 18 and tetrahydro1H-naphtho[2,1-c][1,2] azaphosphole 3-oxides 16 and 27-29 in high yield and diastereoselectivity. Appropriate selection of the base proved to be critical for promoting anionic cyclization of 2-naphthyl derivatives. The dearomatized heterocycles are transformed quantitatively into γ-(N-alkylamino)phosphinic acids by acid hydrolysis of the P-N linkage. Bioactivity assays on five human tumor cell lines for one of these amino acids revealed growth inhibition factors (GI 50) at a micromolar scale. Additionally, evidence for the feasibility of intermolecular nucleophilic dearomatization and sequential nucleophilic attack to both aromatic rings of dinaphthylphosphinamides have been obtained.
