22329-48-2

Upstream product

• 50-00-0 formaldehyd 
• 15547-55-4 1-(3',4'-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 15547-59-8 1-(3,4-dimethoxyphenyl)-3,4-dihydro-6,7-dimethoxy-2-methylisoquinolinium iodide 
• 111427-22-6 N-(3,4-dimethoxybenzoyl)-2-thiazolidine-2-thione 
• 93-07-2 Veratric acid 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 4230-93-7 3,4-dimethoxynitrostyrene 
• 3490-06-0 N-methylhomoveratrylamine 
• 98062-25-0 tert-butyl N-[2-(3,4-dimethoxyphenyl)ethyl]carbamate 
• 1276439-90-7 C₂₀H₂₅NO₅ 
• 16620-96-5 2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 16766-27-1 4-chloro-1,2-dimethoxybenzene 
• 89980-69-8 3,4-dimethoxyphenylmagnesium bromide 
• 1745-07-9 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 74675-38-0 6,7-dimethoxy-1-(3,4-dimethoxyphenyl)-2-methyl-1,3,4,5-tetrahydroisoquinoline N-oxide 
• 152561-03-0 Acetic acid 1-(3,4-dimethoxy-phenyl)-7-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-6-yl ester 

Relevant academic research and scientific papers

Total synthesis of racemic 1-aryl-tetrahydroisoquinoline alkaloids

A new synthetic route was developed for the preparation of natural products cryptostyline I, II, III and 1-phenyl-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline. The Liebeskind-Srogl palladium-catalyzed carbon-carbon cross-coupling protocol was use

Transition-Metal-Free Arylation of N -Alkyl-tetrahydroisoquinolines under Oxidative Conditions: A Convenient Synthesis of C1-Arylated Tetrahydro-isoquinoline Alkaloids

A simple protocol for the C1 arylation of tetrahydroisoquinolines with aryl Grignard reagents via diethyl azodicarboxylate (DEAD) mediated oxidative C-H activation under metal-free conditions has been developed. The target compounds, including some natura

Nucleophilic addition of Lewis acid complexed α-amino carbanions to arynes: Synthesis of 1-aryl- N -methyl-1,2,3,4-tetrahydroisoquinolines

The direct C-1 arylation of N-methyl-1,2,3,4-tetrahydroisoquinolines via coupling of α-amino carbanions derived from Lewis acid complexed tetrahydroisoquinolines and in situ generated arynes is described. This process provides an easy access to the title compounds and a new synthetic route to (±)-cryptostyline alkaloids. Georg Thieme Verlag Stuttgart New York.

Design, synthesis, and biological evaluation of Erythrina alkaloid analogues as neuronal nicotinic acetylcholine receptor antagonists

The synthesis of a new series of Erythrina alkaloid analogues and their pharmacological characterization at various nicotine acetylcholine receptor (nAChR) subtypes are described. The compounds were designed to be simplified analogues of aromatic erythrinanes with the aim of obtaining subtype-selective antagonists for the nAChRs and thereby probe the potential of using these natural products as scaffolds for further ligand optimization. The most selective and potent nAChR ligand to come from the series, 6,7-dimethoxy-2- methyl-1,2,3,4-tetrahydroisoquinoline (3c) (also a natural product by the name of O-methylcorypalline), displayed submicromolar binding affinity toward the α4β2 nAChR with more than 300-fold selectivity over α4β4, α3β4, and α7. Furthermore, this lead structure (which also has inhibitory activity at monoamine oxidases A and B and at the serotonin and norepinephrine transporters) showed antidepressant-like effect in the mouse forced swim test at 30 mg/kg.

A one-pot synthesis of (±) cryptostylines I, II, III

A one-pot synthesis of cryptostylines I, II, III, via the Pictet-Spengler reaction is reported.

Enzymatic resolution of acylates of prochiral phenolic 1-aryl- and 1-arylalkyl-1,2,3,4-tetrahydroisoquinolinols, which possess a Guaiacol-type moiety, by use of immobilized lipase in organic solvent

Enzymatic resolution of acylates of prochiral phenolic 1-aryl, and 1-arylalkyl-1,2,3,4-tetrahydroisoquinolinols, which possess a guaiacol-type moiety by use of lipase immobilized with celite in water-saturated organic solvent gave the corresponding acylates and phenols in moderate optical yields.

Ruthenium dioxide in fluoro acid medium. III. Aplication to the synthesis of aporphinic, homoaporphinic and dibenzazocinic alkaloids. Studies towards the preparation of azafluoranthenic skeleton

Intramolecular oxidative couplings of phenylalkyltetrahydroisoquinoline precursors in aporphinic and homoaporphinic alkaloids by using RuO2,2H2O in fluoro acidic media were performed. A comparative study of our reagent with TTFA has been made with different precursors. The procedure was also extended to the synthesis of one dibenzazocinic alkaloid. Then, we attempted to synthetize the azafluoranthenic ring, using phenolic and non phenolic isoquinoline precursors.

Synthesis of Racemic Cryptostylines I, II, and III by Radical Cyclization

Three 1-phenyl-1,2,3,4-tetrahydroisoquinoline alkaloids, cryptostylines I, II, and III, have been synthesized in racemic forms via an aryl radical-initiated cyclization.

2-BENZOPYRYLIUM SALTS. 34. REACTIONS OF 3-CARBOXY-2-BENZOPYRYLIUM SALTS WITH AMINES. SYNTHESIS OF CYCLIC KETOLS

3-Carboxy-2-benzopyrylium salts form 3-carboxyisoquinolinium salts, their decarboxylated analogs, or products of contraction of the heterocycle, namely, cyclic ketols, depending on the nature of the amine and solvent.Upon treatment with acids, these ketol