155602-65-6

Upstream product

• 18066-68-7 ethyl 3,4-dimethoxyphenylacetate 
• 90149-75-0 ethyl 2-acetyl-4,5-dimethoxyphenylacetate 
• 477338-23-1 methyl methyl 2-(1-butoxyvinyl)-4,5-dimethoxybenzoate 
• 19193-05-6 3,4-dihydro-4-keto-6,7-dimethoxyisocoumarin 
• 477338-26-4 6,7-Dimethoxy-3-[1-phenyl-meth-(Z)-ylidene]-isochroman-1,4-dione 
• 2684-02-8 benzenediazonium 
• 17173-25-0 2-hydroxy-6,7-dimethoxynaphthalene-1,4-dione 
• 15964-79-1 methyl (3,4-dimethoxyphenyl)acetate 
• 17667-32-2 methyl 6-bromo-3,4-dimethoxybenzoate 
• 477338-24-2 methyl 2-acetyl-4,5-dimethoxybenzoate 
• 58657-20-8 4',5'-Dimethoxy-2'-carboxyacetophenon 
• 477338-25-3 2-(2-Bromo-acetyl)-4,5-dimethoxy-benzoic acid 

Relevant academic research and scientific papers

Palladium-catalyzed synthesis of o-acetylbenzoic acids: A new, efficient general route to 2-hydroxy-3-phenyl-1,4-naphthoquinones and indolo[2,3-b]naphthalene-6,11-diones

We describe here a new, efficient general synthesis of o-acetylbenzoic acids by Heck palladium-catalyzed arylation of n-butyl vinyl ether with o-bromobenzoic acid esters and the use of these compounds as starting materials for the synthesis of 3-benzylideneisochroman-1,4-diones, which readily rearrange to 2-hydroxy-3-phenyl-1,4-naphthoquinones. The application of this strategy to the synthesis of indolo[2,3-b]naphthalene-6,11-diones is also described.

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

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.