( 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

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...

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Bibliographic Details
Published in:Tetrahedron 2010-12, Vol.66 (52), p.9986-9995
Main Authors: Treus, Mónica, Salas, Cristian O., Gonazález, Marcos A., Estévez, Juan C., Tapia, Ricardo A., Estévez, Ramón J.
Format: Article
Language:English
Subjects:
Benzo[ c]phenanthridines
Chemistry
Condensed benzenic and aromatic compounds
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Hydrolysis
Isoquinolines
Naphthoquinones
Nitro compounds
Noncondensed benzenic compounds
Organic chemistry
Oxidation
Preparations and properties
Stilbenes
Synthesis (chemistry)
Tetrahedrons
Transformations
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.10.035