56517-12-5

Upstream product

• 1449388-34-4 N-(2-bromo-4,5-dimethoxybenzyl)-N-(naphthalen-1-yl)benzamide 
• 1449388-33-3 N-(2-bromo-4,5-dimethoxybenzyl)-N-(naphthalen-1-yl)acetamide 
• 1449388-32-2 N-(2-bromo-4,5-dimethoxybenzyl)-4-methyl-N-(naphthalen-1-yl)benzenesulfonamide 
• 1449388-31-1 methyl 2-bromo-4,5-dimethoxybenzyl(naphthalen-1-yl)carbamate 
• 575-36-0 1-acetamidonaphthalene 
• 18271-17-5 N-tosyl-1-naphthylamine 
• 5449-00-3 methyl 1-naphthylcarbamate 
• 134-32-7 1-amino-naphthalene 

Relevant academic research and scientific papers

Expeditious approach to pyrrolophenanthridones, phenanthridines, and benzo[ c ]phenanthridines via organocatalytic direct biaryl-coupling promoted by potassium tert -butoxide

A methodology involving a "transition metal-free" intramolecular biaryl-coupling of o-halo-N-arylbenzylamines has been developed in the presence of potassium tert-butoxide and an organic molecule as catalyst. The reaction appears to proceed through KOtBu-promoted intramolecular homolytic aromatic substitution (HAS). Interestingly, this biaryl coupling also works in the presence of potassium tert-butoxide as sole promoter. On extending our approach further, we found that N-acyl 2-bromo-N-arylbenzylamines undergo a one-pot N-deprotection/biaryl coupling followed by oxidation, thus offering an expeditious route to the phenanthridine and benzo[c]phenanthridine skeletons. The strategy has been applied to a concise synthesis of Amaryllidaceae alkaloids viz. oxoassoanine (1b), anhydrolycorinone (1d), 5,6-dihydrobicolorine (2d), trispheridine (2b), and benzo[c]phenanthridines alkaloids dihydronitidine (3b), dihydrochelerythidine (3d), dihydroavicine (3f), nornitidine (3h), and norchelerythrine (3j).