408356-64-9Relevant academic research and scientific papers
Conversion of 3-arylphthalides into anthrones with a methylcarbonyl substituent at the C-10 position
Bieniek, Adam,Bartczak, Monika M.,Epsztajn, Jan
scheme or table, p. 151 - 153 (2009/10/15)
The ortho-lithiation of a benzoic acid anilide followed by condensation with an aryl aldehyde gave a 3-arylphthalide. Reductive alkylation with 1-methoxy-1-trimethylsilyloxyethene gave a substituted aromatic carboxylic acid which was cyclised to an anthro
Application of organolithium and related reagents in synthesis, part 31: Effective conversion of 3-arylphthalides into 2-(1-aryl-3-oxo-4- alkoxycarbonylbutyl) benzoic acids
Bieniek, Adam,Kulikiewicz, Krystyna K.,Bartczak, Monika M.
, p. 3249 - 3259 (2007/10/03)
A convenient three-step protocol preparation of the ortho-alkylated (longchain substituent with terminal methylcarbonyl or acetoacetate moiety) aromatic carboxylic acids 15 or 16 from benzoic acids anilides 10 was developed, which exploited the reductive
Application of organolithium and related reagents in synthesis. Part 25: Novel specific synthesis of the 4-arylisochroman-3-acetic acids via conversion of benzoic acids
Bieniek, Adam,Epsztajn, Jan,Kowalska, Justyna A.,Malinowski, Zbigniew
, p. 9293 - 9295 (2007/10/03)
The transformation of the benzanilides 1 into 4-arylisochroman-3-acetic acids 8 applying the following sequence of reactions is described. At first, the 3-arylphthalides 3 were obtained via metallation [n-BuLi] of benzanilides 1 and subsequent treatment of the generated bis-lithiated anilides 2 with aromatic aldehydes. Next, the 3-arylphthalides 3 were reduced [LiBH4] to phthalanes 5 and then, via reductive metallation [Li/C10H8] and reaction of the generated bis-lithiated species 6 with dimethylformamide, 3-hydroxy-4-arylisochromans 7 were produced. In the final step the isochromans 7 were treated with 1-methoxy-1-trimethylsilyloxyethene in the presence of titanium tetrachloride and furnished 4-arylisochromans-3-acetic acid methyl esters 8 as trans stereoisomers (Ψ-e/e).
