7149-64-6

Upstream product

• 77-78-1 dimethyl sulfate 
• 22990-19-8 1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 80574-72-7 N-formyl-2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 119-61-9 benzophenone 
• 50-00-0 formaldehyd 
• 92885-35-3 2-methyl-3,4-dihydroisoquinolinium cation 
• 100-58-3 phenylmagnesium bromide 
• 67-56-1 methanol 
• 52250-50-7 1-phenyl-3,4-dihydroisoquinoline 
• 1612-65-3 2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 62753-44-0 2-Methyl-3,4-dihydroisoquinolinium bromide 
• 108-90-7 chlorobenzene 
• 64-04-0 phenethylamine 
• 98-88-4 benzoyl chloride 

Downstream Products

• 74675-41-5 2,2-dimethyl-1-phenyl-1,2,3,4-tetrahydro-isoquinolinium; iodide 
• 74675-39-1 2-methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline N-oxide 
• 74688-60-1 3-methyl-1-phenyl-1,3,4,5-tetrahydro-2,3-benzoxazepine 

Relevant academic research and scientific papers

Cp*Ir complex bearing a flexible bridging and functional 2,2′-methylenebibenzimidazole ligand as an auto-tandem catalyst for the synthesis of N-methyl tertiary amines from imines via transfer hydrogenation/N-methylation with methanol

A Cp*Ir complex bearing a flexible bridging and functional 2,2′-methylenebibenzimidazole ligand was designed, synthesized, and found to be a general and efficient auto-tandem catalyst for the synthesis of N-methyl tertiary amines from imines via transfer hydrogenation/N-methylation with methanol as both hydrogen source and methylating reagent. In the presence of [Cp*Ir(2,2′-CH2BiBzImH2)Cl][Cl], a range of desirable products were obtained in high yields with nearly complete selectivities. The reaction is highly attractive due to the highly atom economy, and minimal consumption of chemicals and energy. Notably, this research exhibits new potential of metal–ligand bifunctional catalysts for the activation of methanol as C1 source for organic synthesis.

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.

Concise Redox Deracemization of Secondary and Tertiary Amines with a Tetrahydroisoquinoline Core via a Nonenzymatic Process

A concise deracemization of racemic secondary and tertiary amines with a tetrahydroisoquinoline core has been successfully realized by orchestrating a redox process consisted of N-bromosuccinimide oxidation and iridum-catalyzed asymmetric hydrogenation. This compatible redox combination enables one-pot, single-operation deracemization to generate chiral 1-substituted 1,2,3,4-tetrahydroisoquinolines with up to 98% ee in 93% yield, offering a simple and scalable synthetic technique for chiral amines directly from racemic starting materials.

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.

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.

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

A highly efficient synthesis of 1-methyl-, 1-benzyl-, and 1-phenyl-1,2,3,4-tetrahydroisoquinolines by a modified pummerer reaction

(±)-1-Methyl- (13b), (±)-1-benzyl- (13c), and (±)-1-phenyl- (13d)-1,2,3,4-tetrahydroisoquinolines, which are supposed to participate in the pathogenesis of Parkinson's disease, were prepared by using a modified Pummerer reaction as a key step in excellent overall yields from the commercially available ketones (4b-c).

A practical triphenylcarbenium tetrafluoroborate mediated one-pot synthesis of 1-substituted N-alkyl-1,2,3,4-tetrahydroisoquinolines

Treatment of 2-methyl-1,2,3,4-tetrahydroisoquinoline (1) with 1-2 molar equivalents of triphenylcarbenium tetrafluoroborate at 20°C in either chloroform or acetonitrile resulted in the formation of 2-methyl-3,4-dihydroisoquinolinium tetrafluoroborate (2), whereas triethylamine and N-methylpiperidine were unaffected under these reaction conditions. This hydride abstraction was exploited in a one-pot preparation of 1-functionalized 2-alkyl-1,2,3,4-tetrahydroisoquinolines. Thus, treatment of 2 with aqueous potassium hydroxide afforded 1-hydroxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (9) (61% from 1). Similarly, potassium cyanide in acetonitrile provided 1-cyano-2-methyl-1,2,3,4-tetrahydroisoquinoline (10, 77%). Quenching of 2 with Grignard reagents in tetrahydrofuran afforded the corresponding 1-alkyl and 1-aryl substituted tetrahydroisoquinolines (31 to 78%). Interestingly, nitrile 10 reacted very rapidly (2 min at 0°C) with phenylmagnesium bromide to give 2-methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline (3, 100%), but failed to react with excess phenyllithium even at 20°C.

Phencyclidine-like Effects of Tetrahydroisoquinolines and Related Compounds

A series of 1,2,3,4-tetrahydroisoquinolines, tetrahydrothienopyridines, and related compounds were evaluated for their ability to inhibit binding of -1--N-allylnormetazocine to phencyclidine (PCP) and ? receptors, respectively.A representative series of compounds was evaluated in behavioral assays to determine the ability of the compounds to induce PCP-like stereotyped behavior and ataxia.All of the compounds caused stereotyped behavior and ataxia, indicating their agonist actions at the PCP site.