4008-69-9

Upstream product

• 6075-62-3 6,7-dimethoxy-2-methyl-1-phenyl-3,4-dihydroisoquinolinium iodide 
• 5833-05-6 6,7-dimethoxy-2-methyl-1-phenyl-isoquinolinium; iodide 
• 16620-96-5 2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 108-90-7 chlorobenzene 
• 4118-36-9 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 485-80-3 S-adenosyl-L-methionine 
• 32749-01-2 3,4-dihydro-6,7-dimethoxy-2-methylisoquinolinium 
• 100-58-3 phenylmagnesium bromide 
• 78373-75-8 bromure de dimethoxy-6,7 methyl-2 dihydro-3,4 isoquinoleinium 
• 98062-25-0 tert-butyl N-[2-(3,4-dimethoxyphenyl)ethyl]carbamate 
• 3490-06-0 N-methylhomoveratrylamine 
• 4230-93-7 3,4-dimethoxynitrostyrene 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 

Downstream Products

• 74675-30-2 6,7-Dimethoxy-2-methyl-1-phenyl-3,4-dihydro-1H-isoquinoline 2-oxide 
• 74675-30-2 6,7-dimethoxy-2-methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline cis-N-oxide 
• 74675-30-2 6,7-dimethoxy-2-methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline trans-N-oxide 
• 20412-85-5 2-benzyl-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 24770-55-6 6,7-dimethoxy-2,2-dimethyl-1-phenyl-1,2,3,4-tetrahydroisoquinolinium iodide 

Relevant academic research and scientific papers

Synthesis and dopaminergic activity of a series of new 1-aryl tetrahydroisoquinolines and 2-substituted 1-aryl-3-tetrahydrobenzazepines

A series of new 1-aryl-6,7-dihydroxy tetrahydroisoquinolines with several substitution patterns in the 1-aryl group at C-1 were prepared in good yields. The influence of each substituent on the affinity and selectivity for D1 and D2

Structure and Biocatalytic Scope of Coclaurine N-Methyltransferase

Benzylisoquinoline alkaloids (BIAs) are a structurally diverse family of plant secondary metabolites, which have been exploited to develop analgesics, antibiotics, antitumor agents, and other therapeutic agents. Biosynthesis of BIAs proceeds via a common pathway from tyrosine to (S)-reticulene at which point the pathway diverges. Coclaurine N-methyltransferase (CNMT) is a key enzyme in the pathway to (S)-reticulene, installing the N-methyl substituent that is essential for the bioactivity of many BIAs. In this paper, we describe the first crystal structure of CNMT which, along with mutagenesis studies, defines the enzymes active site architecture. The specificity of CNMT was also explored with a range of natural and synthetic substrates as well as co-factor analogues. Knowledge from this study could be used to generate improved CNMT variants required to produce BIAs or synthetic derivatives.

Oxidation of Trialkylamines by BrCCl3: Scope, Applications and Mechanistic Aspects

The catalyst-free photochemical reaction of trialkylamines and BrCCl3 induced by visible light was investigated. The outcome of the reaction was found to depend strongly on the nature of the amine substrates. N-Methyl-1,2,3,4-tetrahydroisoquino

Contra-thermodynamic Hydrogen Atom Abstraction in the Selective C-H Functionalization of Trialkylamine N-CH3 Groups

We report a simple one-pot protocol that affords functionalization of N-CH3 groups in N-methyl-N,N-dialkylamines with high selectivity over N-CH2R or N-CHR2 groups. The radical cation DABCO+?, prepared in situ by oxidation of DABCO with a triarylaminium salt, effects highly selective and contra-thermodynamic C-H abstraction from N-CH3 groups. The intermediates that result react in situ with organometallic nucleophiles in a single pot, affording novel and highly selective homologation of N-CH3 groups. Chemoselectivity, scalability, and recyclability of reagents are demonstrated, and a mechanistic proposal is corroborated by computational and experimental results. The utility of the transformation is demonstrated in the late-stage site-selective functionalization of natural products and pharmaceuticals, allowing rapid derivatization for investigation of structure-activity relationships.

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.

One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates

Nucleophilic trapping of iminium salts generated via oxidative functionalisation of tertiary amines is well established with stabilised carbon nucleophiles. The few reports of organometallic additions have limited scope of substrate and organometallic nucleophile. We report a novel, one-pot methodology that functionalises N - substituted tetrahydroisoquinolines by visible lightassisted photooxidation, followed by trapping of the resultant iminium ions with organometallic nucleophiles. This affords 1,2-disubstituted tetrahydroisoquinolines in moderate to excellent yields.

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.

Diastereoselective synthesis of 1,2-disubstituted 2,3,4,5-tetrahydro1H-3- benzazepines by means of the Stevens rearrangement

1,2-Disubstituted 2,3,4,5-tetrahydro-1H-3-benzazepines were conveniently obtained by making use of the regio- and diastereoselective Stevens rearrangement of the corresponding isoquinolinium salts with 1,8-diazabicyclo[5.4.0]undec-7-ene in acetonitrile, T