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A new route to 3-(2-vinylphenyl)-2-methyl-2H-isoquinolin-1-ones and benzo[c]phenanthridines: total synthesis of fagaronine

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

Book ID
104251430
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
88 KB
Volume
43
Category
Article
ISSN
0040-4039

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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 be transformed into 3-(2-vinylphenyl)-2-methyl-2H-isoquinolin-1-ones by Bischler-Napieralski reactions, and thence into benzo[c]phenanthridin-6-ones. The use of this route for a new total synthesis of fagaronine is described.

📜 SIMILAR VOLUMES

A novel C–N cleavage in isoquinolines al
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
✍ Mónica Treus; Juan C Estévez; Luis Castedo; Ramón J Estévez 📂 Article 📅 2000 🏛 Elsevier Science 🌐 French ⚖ 93 KB

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]phe

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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