55580-65-9

Upstream product

• 27644-76-4 2-(p-methoxyphenyl)-4,4-dimethyloxazolidine 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 123-11-5 4-methoxy-benzaldehyde 
• 66040-50-4 N-(4-methoxybenzylidene)-2-(3',4'-dimethoxyphenyl)ethylamine 
• 66040-50-4 [2-(3,4-Dimethoxy-phenyl)-ethyl]-[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-amine 

Downstream Products

• 1007356-62-8 C₂₇H₂₉NO₅ 
• 1007356-64-0 C₂₆H₂₉NO₃ 
• 1007356-63-9 C₂₅H₂₆FNO₃ 
• 66040-39-9 N-acetyl-6,7-dimethoxy-1-(4'-methoxyphenyl)-1,2,3,4-tetrahydrioisoquinoline 
• 15547-67-8 6,7-dimethoxy-1-(4-methoxy-phenyl)-isoquinoline 
• 15462-83-6 6,7-dimethoxy-1-<(para-methoxy)phenyl>-3,4-dihydroisoquinoline 

Relevant academic research and scientific papers

Synthesis of 1-aryltetrahydroisoquinoline alkaloids and their analogs

Three alkaloids of the cryptostylin series and 20 monomolecular and 3 bimolecular 1-aryltetrahydroisoquinoline derivatives were prepared using the Picte-Spengler reaction.

Synthesis and structure - Active relationship of 1-aryl-6,7-dimethoxy-1,2, 3,4-tetrahydroisoquinoline anticonvulsants

We have previously disclosed that some 6,7-dimethoxyisoquinoline derivatives are able to produce anticonvulsant effects in different animal models of epilepsy. Following these studies this paper describes the synthesis of a small series of new 1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines strictly related to previously reported analogues. This novel series of isoquinolines was designed on the basis of well defined structure-active relationship (SAR) information already acquired for this class of anticonvulsant agents. The pharmacological effects of the new synthesized compounds were evaluated against audiogenic seizures in Dilute Brown non-Agouti (DBA/2) mice. The preliminary pharmacological screening led to the identification of a new active molecule the 2-acetyl-1-(4′-methylphenyl)-6,7-dimethoxy-1,2,3,4- tetrahydroisoquinoline (6d) that displayed significant anticonvulsant activity. Computational studies helped to rationalize these obtained pharmacological results.

Strategies and synthetic methods directed toward the preparation of libraries of substituted isoquinolines

Strategies for the production of substituted isoquinoline libraries were developed and explored. Routes involving microwave-assisted variants of the Bischler-Napieralski or Pictet-Spengler reaction allowed for cyclization of substituted β-arylethylamine derivatives. The dihydroisoquinolines and tetrahydroisoquinolines thus generated could then be oxidized to their corresponding isoquinoline analogues. An alternate strategy, however, involving the preparation and activation of isoquinolin-1(2H)-ones is demonstrated to be a more practical, rapid, and efficient route to C1- and C4-substituted isoquinoline libraries.

O-Benzenedisulfonimide as a reusable acid catalyst for an easy, efficient, and green synthesis of tetrahydroisoquinolines and tetrahydro-β-carbolines through Pictet-Spengler reaction

The synthesis of tetrahydroisoquinolines and tetrahydro-β-carbolines, using the Pictet-Spengler reaction, was carried out in the presence of a catalytic amount of o-benzenedisulfonimide, which worked as a Br?nsted acid organocatalyst. The reaction conditi

1-Aryl-tetrahydroisoquinoline analogs as active anti-HIV agents in vitro

A series of 1-aryl-6,7-dihydroxyl(methoxy)-1,2,3,4-tetrahydroisoquinolines (compounds 1-36) were synthesized via Pictet-Spengler cyclization. All the synthesized compounds were assayed for activities against HIV-1IIIB in C8166 cell cultures by

Synthesis of benzoazocines from substituted tetrahydroisoquinolines and activated alkynes in a tetrahydropyridine ring expansion

Tetrahydroisoquinolines underwent tandem piperidine ring enlargement in the presence of activated alkynes in acetonitrile or methanol, producing tetrahydrobenzo[d]azocines in high yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Tandem enlargement of the tetrahydropyridine ring in 1-aryl-tetrahydroisoquinolines using activated alkynes-a new and effective synthesis of benzoazocines

Tetrahydroisoquinolines 3a-e underwent piperidine ring enlargement under the action of activated alkynes, giving benzoazocines 4, 5 and 7-11 in high yields.

Synthesis of carbon-11 and fluorine-18 labeled N-acetyl-1-aryl-6,7- dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives as new potential PET AMPA receptor ligands

New carbon-11 and fluorine-18 labeled N-acetyl-1-aryl-6,7-dimethoxy-1,2,3, 4-tetrahydroisoquinoline derivatives were designed and synthesized as potential positron emission tomography AMPA (2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl) propionic acid) recep

Racemic and diastereoselective synthesis of aryl and heteroaryl tetrahydroisoquinolines via the Pictet-Spengler reaction

New tetrahydroisoquinolines were synthesized by the Pictet-Spengler reaction. Influence of a wide range of aryl and heteroaryl aldehydes, was investigated in the cyclization step with 3,4-dimethoxyphenylethylamine 1, L-DOPA 2 and L-3,4-dimethoxyphenylalan

Synthesis and pharmacological properties of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives

Some selected 1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives were synthesized and evaluated as the β-adrenoceptor agents. Some of the compounds showed a weak agonistic or antagonistic activity on these receptors.