114253-63-3Relevant academic research and scientific papers
Synthesis of benzo[c]phenanthridine alkaloids by Pd(OAc) 2-induced direct aromatic carbonylation
Kumazawa, Eri,Tokuhashi, Takashi,Horibata, Akiyoshi,Tokuda, Masao,Orito, Kazuhiko,Kurono, Nobuhito,Senboku, Hisanori,Ohkuma, Takashi
, p. 4622 - 4633,12 (2020/08/31)
The Pd(OAc)2-induced carbonylation of alkoxy-substituted 1-amino-2-phenyltetralins and 1-amino-2-phenylnaphthalenes was examined to provide the benzo[c]phenanthridine ring system. The carbonylation of substrates containing methylenedioxy groups
(Z)-Ethyl 2-phenyl-1-(2-vinylphenyl)vinylcarbamates. Part 1: Synthesis and preliminary studies on their divergent transformation into benzo[c] phenanthridines and 2-phenyl-1,4-naphthoquinones
Treus, Mónica,Salas, Cristian O.,Gonazález, Marcos A.,Estévez, Juan C.,Tapia, Ricardo A.,Estévez, Ramón J.
experimental part, p. 9986 - 9995 (2011/02/23)
Treatment of N-carbethoxy-1-benzylideneisoquinolines with LDA gives N-ethoxycarbonyl-1-amino-1-(2-vinylphenyl)-2-phenylethylenes, which can easily be transformed into N-carbethoxy-1-amino-2-phenylnaphthalenes. Bischler-Napieralski reaction of these latter
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
A novel C-N cleavage in isoquinolines allowing the first direct transformation of 1-benzylisoquinolines into benzo[c]phenanthridines and a new route to 2-phenyl-1,4-naphthoquinones
Treus,Estevez,Castedo,Estevez
, p. 6351 - 6353 (2007/10/03)
Treatment of N-carbethoxy-1-benzylideneisoquinolines with LDA gives N-ethoxycarbonyl-1-amino-1-(2-vinylphenyl)-2-phenylethylenes, which can easily be transformed into N-carbethoxy-1-amino-2-phenyl-naphthalenes. Bichler-Napieralski reaction of these latter compounds affords the corresponding benzo[c]-phenanthridines, while their hydrolysis and subsequent oxidation constitutes a route to 2-phenyl-1,4-naphthoquinones. (C) 2000 Elsevier Science Ltd.
Applications of a novel carbon-nitrogen bond cleavage reaction: Part IV - A new biomimetic synthesis of benzo[c]phenanthridine alkaloids
Lal, Bansi,Gidwani, Ramesh M.
, p. 679 - 681 (2007/10/03)
A highly practical synthesis of benzo[c]phenanthridine alkaloids nitidine and 2-methoxyfagaronine has been developed from the corresponding protoberberines. The 8-oxoprotoberberines 1-3 on reaction with NaH and DMF give the C-N bond cleavage intermediates
A common and general access to berberine and benzo [c] phenanthridine alkaloids
Beugelmans,Bois-Choussy
, p. 8285 - 8294 (2007/10/02)
The S(RN)1 reactions between o-iodobenzamides and the enolate anion from 2-acetyl homoveratric acid lead to key tricyclic compounds which are easily converted to either berberine or benzo [c] phenanthridine ring systems providing thus a highly-yielding and versatile access to both classes of alkaloids.
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.
