55178-75-1

Upstream product

• 128942-60-9 2-(methyl-veratryl-amino)-1-phenyl-ethanol 
• 128942-54-1 2-[(3,4-Dimethoxy-benzyl)-methyl-amino]-1-phenyl-ethanone 
• 63-64-9 N-methylveratrylamine 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 1147090-58-1 2-(N-(3,4-dimethoxybenzyl)-N-methylamino)-1-phenylethyl N',N'-diisopropylcarbamate 
• 16620-96-5 2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 108-90-7 chlorobenzene 
• 91-16-7 1,2-dimethoxybenzene 
• 88953-56-4 3-methyl-5-phenyloxazolidine 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

5-Aryloxazolidines as Reagents for Double Alkylation of Arenes: A Novel Synthesis of 4-Aryltetrahydroisoquinolines

5-Aryloxazolidines react with arenes under Lewis or Br?nsted acid conditions via the Friedel-Crafts/Pictet-Spengler double alkylation sequence to give alkaloid-like 4-aryltetrahydroisoquinolines in 12-94% yields. Three approaches for the controlled insertion of substituents into the target molecules and application of oxazolidine derivatives such as 1-arylethanol-2-amines or 4-hydroxytetrahydroisoquinolines in the alkylation of arenes are also described. An unprecedented two-step easily scalable synthesis of the 4-aryltetrahydroisoquinoline core from aromatic aldehyde was achieved applying oxazolidine methodology.

Nucleophilic addition of β-amino carbanions to arynes: One-pot synthesis of 4-aryl-N-methyl-1,2,3,4-tetrahydroisoquinolines

A novel approach for the direct C-4 arylation of N-methyl-1,2,3,4- tetrahydroisoquinolines by nucleophilic addition of β-aminocarbanions to benzynes is described which provides a one-pot procedure for synthesis of the title compounds.

Direct syntheses of 4-aryl-1,2,3,4-tetrahydroisoquinolines and 1-aryl-2,3,4,5-tetrahydro-3-benzoazepines via hydroamination of enol carbamates

An efficient and simple procedure for the syntheses of 4-aryl-1,2,3,4-tetrahydroisoquinolines and 1-aryl-2,3,4,5-tetrahydro-3-benzoazepines has been developed. The approach uses easily available starting materials and requires just three steps. The hydroamination of an enol carbamate is the key step. This general and direct method has been applied to the total synthesis of the natural alkaloid cherylline and to biologically active 3-benzoazepines as well.

A New Synthesis of 1,2,3,4-Tetrahydro-2-methyl-4-phenylisoquinolines

1,2,3,4-Tetrahydro-2-methyl-4-phenylisoquinolines 6 are obtained from aromatic aldehydes 1, methyl amine and α-haloacetophenones 2 in the presence of sodium borohydride followed by cyclization with sulfuric acid and zinc in methanol.