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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

✍ Scribed by Mónica Treus; Juan C Estévez; Luis Castedo; Ramón J Estévez

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 93 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)01052-2

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✦ Synopsis

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. Bichler±Napieralski reaction of these latter compounds aords the corresponding benzo[c]phenanthridines, while their hydrolysis and subsequent oxidation constitutes a route to 2-phenyl-1,4naphthoquinones.

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ChemInform Abstract: A Novel C—N Cleavag

ChemInform Abstract: 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.

✍ Monica Treus; Juan C. Estevez; Luis Castedo; Ramon J. Estevez 📂 Article 📅 2000 🏛 John Wiley and Sons ⚖ 32 KB 👁 2 views

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