(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

作者：Treus Monica; Salas Cristian O; Gonazalez Marcos A; Estevez Juan C; Tapia Ricardo A^*; Estevez Ramon J

来源：Tetrahedron, 2010, 66(52): 9986-9995.

DOI：10.1016/j.tet.2010.10.035

• Stilbenes
• Isoquinolines
• Benzo[c]phenanthridines
• Naphthoquinones
• Nitro compounds

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 compounds affords the corresponding benzo[c]phenanthridines, while their hydrolysis and subsequent oxidation constitutes a novel route to 2-phenyl-1,4-naphthoquinones.

• 出版日期2010-12-24