125455-89-2Relevant articles and documents
A new route to 3-(2-vinylphenyl)-2-methyl-2H-isoquinolin-1-ones and benzo[c]phenanthridines: Total synthesis of fagaronine
Treus, Mónica,Estévez, Juan C,Castedo, Luis,Estévez, Ramón J
, p. 5323 - 5325 (2007/10/03)
Treatment of N-carbethoxy-1-benzylideneisoquinolines with LDA gives N-ethoxycarbonyl-1-amino-1-(2-vinylphenyl)-2-phenylethylenes, which can be transformed into 3-(2-vinylphenyl)-2-methyl-2H-isoquinolin-1-ones by Bischler-Napieralski reactions, and thence
BENZOPHENANTHRIDES. XV. SYNTHESIS OF O-METHYLFAGARONINE IODIDE AND CHLORIDE FROM 13α-HYDROXYXYLOPININE
Sazonova, N. M.,Levina, I. I.,Sladkov, V. I.,Suvorov, N. N.
, p. 1751 - 1756 (2007/10/02)
Hydroborination of 3-(2-vinyl-4,5-dimethoxyphenyl)-6,7-dimethoxy-2-methyl-1,2-dihydro-1-isoquinolone gave 3--6,7-dimethoxy-2-methylisoquinolin-1-one, which was converted by the action of various oxidizing agents into a benzophenanthridone derivative. 5-Methyl-5,6-dihydro-2,3,8,9-tetramethoxybenzophenanthridine, obtained from the above benzophenanthridone by reduction with LiAlH4 in tetrahydrofuran at 0 deg C, was converted into O-methylfagaronine iodide by boiling in an ethanolic solution of I2 in the presence of Na acetate.On exchanging I- by Cl-, O-methylfagaronine chloride was obtained in a quantitative yield in boiling methanol with an excess of AgCl.
BENZOPHENANTHRIDINES. IX. SYNTHESIS OF 11-METHYL-C-NORFAGARONINE METHYL ETHER CHLORIDE FROM (+/-)-13α-HYDROXYXYLOPININE
Sazanova, N. M.,Sladkov, V. I.,Suvorov, N. N.
, p. 1167 - 1169 (2007/10/02)
The previously unknown chloride of 11-methyl-C-norfagaronine methyl ether was synthesized from (+/-)-13α-hydroxyxylopinine in four stages.A reduction in the number of stages in the biometic synthesis of the analog of benzophenanthridine alkaloids was achieved by the Hofmann degradation of α-N-methyl-(+/-)-13α-hydroxyxylopinine p-toluenesulfonate, accompanied by dehydration and oxidation.