154490-65-0Relevant academic research and scientific papers
(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 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.
A formal new access to the benzo[c]phenanthridine alkaloids, synthesis of Nitidine and O-Methyl Fagaronine analogues
Janin,Bisagni
, p. 10305 - 10316 (2007/10/02)
Previously unreported 2-aryl-1-naphthylamines were obtained in good yields from 2-aryl-1-tetraloneoximes by using the Semmler-Wolf reaction but omitting the acetic anhydride usually present in the reaction mixture. From these amines, through the thermal cyclization of their corresponding ethyl carbamates, a new access to the benzo[c]phenanthridin-6(5H)-ones was found. Preparation of water-soluble Nitidine and O-Methyl Fagaronine analogues bearing an alkylamino side chain on the C-6 position was achieved from these compounds.
