3423-37-8

Upstream product

• 4876-00-0 1-benzyl-6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 103-82-2 phenylacetic acid 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 122-78-1 phenylacetaldehyde 
• 20359-09-5 (6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)(phenyl)methanone 
• 4876-02-2 N-(3,4-dimethoxyphenethyl)-phenyl acetamide 
• 103-80-0 phenylacetyl chloride 
• 101-97-3 Ethyl 2-phenylethanoate 
• 20226-04-4 1-benzyl-6,7-dimethoxy-3,4-dihydroisoquinoline-hydrochloride 

Downstream Products

• 114873-36-8 1-Benzyl-2-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline; hydrochloride 
• 120034-55-1 (1S)-1,2,3,4-tetrahydro-1-benzoyl-6,7-dimethoxy-2-<((R)-1-phenylethyl)carbamoyl>isoquinoline 
• 120034-56-2 (1R)-1,2,3,4-tetrahydro-1-benzoyl-6,7-dimethoxy-2-<((R)-1-phenylethyl)carbamoyl>isoquinoline 
• 91-01-0 1,1-Diphenylmethanol 
• 464-72-2 tetraphenylethane-1,2-diol 
• 23818-73-7 6,7-dimethoxy-1-benzylisoquinoline 
• 861429-63-2 [3-(1-benzyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-1-(2-cyano-pyrrolidine-1-carbonyl)-3-oxo-propyl]-carbamic acid tert-butyl ester 
• 3423-13-0 1-benzyl-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline 
• 47145-37-9 (1R)-1,2,3,4-tetrahydro-1-benzoyl-6,7-dimethoxyisoquinoline 
• 47145-36-8 (1S)-1-benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 14919-82-5 6,7DHBnTIQ 
• 14347-96-7 6,7-Dimethoxy-2-ethyl-1-benzyl-1,2,3,4-tetrahydroisochinolin 
• 1007356-48-0 C₂₆H₂₉NO₂ 
• 876066-63-6 1-benzyl-5,8-dichloro-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride 

Relevant academic research and scientific papers

Enhancement of the carbamate activation rate enabled syntheses of tetracyclic benzolactams: 8-oxoberbines and their 5- And 7-membered C-ring homologues

A route to the direct amidation of aromatic-ring-tetheredN-carbamoyl tetrahydroisoquinoline substrates was developed. This route enabled general access to 8-oxoberberines and their 5- and 7- membered C-ring homologues. It overcomes the undesired tandem side-reactions that result in the destruction of the isoquinoline backbone, which inevitably occurred under our previously reported superacidic carbamate activation method.

Development of Pd(OAc)2-catalyzed tandem oxidation of C[sbnd]N, C[sbnd]C, and C(sp3)–H bonds: Concise synthesis of 1-aroylisoquinoline, oxoaporphine, and 8-oxyprotoberberine alkaloids

A catalytic tandem oxidation of C[sbnd]N, C[sbnd]C, and C(sp3)–H bonds is developed. This tandem oxidation is applied to two-step total syntheses of papaveraldine and pulcheotine A. Additionally, the total synthesis of liriodenine is achieved in six steps from homopiperonyl alcohol and 2-bromophenylacetonitrile by applying this catalytic tandem oxidation. Moreover, the direct conversion of xylopinine to 8-oxypseudopalmatine in a 76% yield demonstrates the versatility of this catalytic reaction.

Synthesis of 8-oxoberbines and related benzolactams by Pd(OAc) 2-catalyzed direct aromatic carbonylation

A variety of alkoxy-substituted benzolactams with a berbine or yohimbane skeleton were prepared from 1-benzyl-1,2,3,4-tetrahydroisoquinolines or 1-benzyl-1,2,3,4-tetrahydro-β-carbolines by a phosphine-free Pd(II)-catalyzed direct aromatic carbonylation in a Pd(OAc)2-Cu(OAc) 2 catalytic system. The site selectivity was compared with that of the carbonylation with Pd(OAc)2 or Pd(OAc)2·2 PPh3, respectively.

Oxidation of 1-benzyldihydroisoquinolines or 1- benzyltetrahydroisoquinolines with dioxygen to 1-benzoylisoquinolines

An environmental-benign methodology to synthesize 1-benzoylisoquinolines from 1-benzyl-3, 4-dihydroisoquinolines or 1-benzyl-1,2,3,4- tetrahydroisoquinolines using dioxygen as an oxidant was developed. This methodology in combination with Bischler-Napieralski reaction leads to a facile synthesis of 1-benzoylisoquinolines from phenylacetic acids and phenylethanamines.

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

The synthesis of N-phenoxyethyl-1-substituted-1,2,3,4-tetrahydroisoquinolines and their α1-adrenoceptor blocking activity

A series of phenoxyisoquinolines, N-phenoxyethyl-1-(2-nitrophenyl)-1,2,3,4-THIQs 3a-3d, N-phenoxyethyl-1-benzyl-1,2,3,4-THIQ 3e, N-phenoxyethyl-1-(2-aminophenyl)-1,2,3,4-THIQs 5f-5i, N-phenoxyethyl-1-(2-phenoxyethylaminophenyl)-1,2,3,4-THIQs 5f′-5i′, have

A highly enantioselective access to tetrahydroisoquinoline and β-carboline alkaloids with simple noyori-type catalysts in aqueous media

Silver enhancement: A very convenient modified protocol for the enantioselective transfer hydrogenation of dihydroisoquinoline skeletons under aqueous conditions is reported. Unmodified Noyori ligands can be used and the activity of the catalyst is greatly enhanced with silver additives (see scheme). The protocol was used in a very short synthesis of the alkaloids (S)-harmicine and (S)-crispine.

Unexpected unique behavior of spiro-isoquinolines with a cyclohexadienone system in attempted dienone-phenol rearrangement

8',9'-Dimethoxy-1',5',6',10b'-tetrahydro-4H-spiro(cyclohexa-2,5-diene-1,2'-pyrrolo[2,1-a]isoquinoline)-3',4-dione 2 with a basic skeleton of a natural product, annnosqualine, exhibited unique behavior in a dienone-phenol rearrangement. Treatment of 2 with trifluoroacetic acid gave a simple 1-benzylisoquinoline alkaloid, norarmepavine 4. Plausible reaction mechanism for the observed transformation is also described.

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.

Synthesis of (±)-Glaucine and (±)-Neospirodienone via an One-Pot Bischler-Napieralski Reaction and Oxidative Coupling by a Hypervalent Iodine Reagent

Condensation of 3,4-dimethoxybenzeneethanamine (3d) and various benzeneacetic acids, i.e., 4a-e, via a practical and efficient one-pot Bischler-Napieralski reaction, followed by NaBH4 reduction, produced a series of 1-benzyl-1,2,3,4-tetrahydroisoquinolines, i.e., 5a-e, in satisfactory yields (Scheme 3). Oxidative coupling of the N-acyl and N-methyl derivatives 6a-e of the latter with hypervalent iodine ([IPh(CF 3COO)2]) yielded products with two different skeletons (Scheme 4). The major products from N-acyl derivatives 6a-c were (±)-N-acylneospirodienones 2a-c, while the minor was the 3,4-dihydroisoquinoline 7. (±)-Glaucine (1), however, was the major product starting from N-methyl derivative 6e. Possible reaction mechanisms for the formation of these two types of skeleton are proposed (Scheme 5).