76306-41-7

Upstream product

• 76306-60-0 (+/-)-N-acetyl-α-phenyl-β-(3,4-dimethoxy)phenethylamine 
• 29955-23-5 1-Phenyl-2-(3,4-dimethoxyphenyl)ethanone 
• 1128112-70-8 3,4-dimethoxy-7-methyl-N-[(1E)-phenylmethylene]bicyclo[4.2.0]octa-1,3,5-trien-7-amine 
• 76306-68-8 N-<2-(3,4-dimethoxyphenyl)-1-phenylethyl>formamide 
• 135365-14-9 8,9-Dimethoxy-10b-methyl-5-phenyl-6,10b-dihydro-5H-oxazolo[2,3-a]isoquinoline-2,3-dione 
• 155955-78-5 3,4-dimethoxyphenylacetic acid N,O-dimethylhydroxyamide 

Downstream Products

• 104151-19-1 6,7-dimethoxy-1-methyl-3-phenyl-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

Synthesis of 3,4-dihydroisoquinolines by a C(sp3)-H activation/electrocyclization strategy: Total synthesis of coralydine

(Chemical Equation Presented) Thanks to C-H activation: 3-Aryl-3,4-dihydroisoquinolines (2) are synthesized from bromobenzenes (1) by a sequence comprising a C(sp3)-H activation, a Curtius rearrangement, and a tandem electrocyclic ring-opening/

A Modified Bischler-Napieralski Procedure for the Synthesis of 3-Aryl-3,4-dihydroisoquinolines

A modification of the Bischler-Napieralski reaction for the cyclization of (1,2-diphenylethyl)amides to the 3-aryl-3,4-dihydroisoquinolines is presented.Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by its conversion to an N-acyliminium intermediate with oxalyl chloride-FeCl3.Removal of the oxalyl group in refluxing MeOH-sulfuric acid provides the 3,4-dihydroisoquinolines in moderate to high yields.The method is also highly effective with (2-phenylethyl)amides.

Unusual Products in Bischler-Napieralski Reaction

Bischler-Napieralski cyclisation of the benzoyl and acetyl derivatives (I and II) using PCl5 gives the dihydroisoquinolines only when these derivatives have no dimethoxy or methylenedioxy substituents in the α-phenyl ring.All the formyl derivatives (III), however, give the dihydroisoquinolines in good yield.Stilbenes (VII), meso-stilbene dichlorides (VIII) and the hydrindane derivative (X) are obtained as neutral products in the above reactions, sometimes as the sole products.The results clearly demonstrate the occurrence of side raections in this cyclisation reaction even when there are activating groups favouring cycldehydration.