15889-93-7

Upstream product

• 56014-48-3 N-<2-(3,4-dimethoxyphenyl)ethyl>proline 
• 104058-44-8 8,9-bis(methyloxy)-2,3,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-5(1H)-one 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 4230-93-7 3,4-dimethoxynitrostyrene 
• 123190-12-5 2-(2-bromoethyl)-4,5-(dimethoxy)benzaldehyde 
• 39662-45-8 N-<2-(3,4-dimethoxyphenyl)ethyl>succinimide 
• 39662-50-5 1-[2-(3,4-dimethoxyphenyl)ethyl]-5-hydroxy-2-pyrrolidinone 
• 73357-23-0 2-(4,5-dimethoxy-2-nitrophenyl)ethan-1-ol 
• 65907-71-3 1,2-dimethoxy-4-nitro-5-vinylbenzene 
• 20357-25-9 6-nitroveratraldehyde 
• 1745-07-9 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 127119-08-8 3,4-dihydro-6,7-dimethoxy-2(1H)-isoquinolinecarboxylic acid 1,1-dimethylethyl ester 

Downstream Products

• 1345019-56-8 C₁₀H₁₅OPS*C₁₄H₁₉NO₂ 
• 1345019-54-6 C₁₀H₁₅OPS*C₁₄H₁₉NO₂ 

Relevant academic research and scientific papers

Direct C-H Allylation of N-Acyl/Sulfonyl Tetrahydroisoquinolines and Analogues

A highly efficient direct C-H allylation reaction at the α position of N-acyl/sulfonyl tetrahydroisoquinolines under mild conditions was developed. The reaction was also suitable for allylation of other protected nitrogen-containing heterocycles. Several

One-pot synthesis of (±)-crispine A and its C-ring-substituted analogs

A straightforward access to crispine A and C-ring-substituted analogs by 1,4-addition of a deprotonated α-amino nitrile to α,β- unsaturated carbonyl compounds is described. If the reduction step is omitted, substituted 5,6-dihydropyrrolo[2,1-α]isoquinolin

Total synthesis of the antitumor active pyrrolo[2,1-a]isoquinoline alkaloid (±)-crispine a

Addition of a propargyl Grignard reagent to 3,4-dihydro-6,7- dimethoxyisoquinoline, silver(I)-promoted oxidative cyclization, and chemoselective hydrogenation of the pyrrole ring provide a simple three-step route to the antitumor active pyrrolo[2,1-a]isoquinoline alkaloid (±)-crispine A.

Facile two-step synthesis of crispine A and harmicine by cyclopropylimine rearrangement

The synthesis of 4 and 8 is reported. These intermediates are obtained by a one-pot tandem cyclization of 1 and 6, respectively, via Bischler Napieralski reaction followed by cyclopropylimine rearrangement. Compounds 4 and 8 were reduced by sodium borohydride in methanol to afford cytotoxic alkaloid (±)-crispine A and antileishmania compound (±)-harmicine.

Direct Arylation of Distal and Proximal C(sp3)-H Bonds of t-Amines with Aryl Diazonium Tetrafluoroborates via Photoredox Catalysis

A visible light-mediated arylation protocol for t-amines has been reported through the coupling of γ- and α-amino alkyl radicals with different aryl diazonium salts using Ru(bpy)3Cl2·6H2O as a photocatalyst. Structurally different 9-aryl-9,10-dihydroacridine, 1-aryl tetrahydroisoquinoline, hexahydropyrrolo[2,1-a]isoquinoline, and hexahydro-2H-pyrido[2,1-a]isoquinoline frameworks with different substitution patterns have been synthesized in good yield using this methodology.

One-pot tandem route to fused indolizidines and quinolizidines: Application in the synthesis of alkaloids and bioactive compounds

Fused indolizidines and quinolizidines are important skeletons in a variety of natural products and pharmacologically important compounds. A one-pot tandem route from amide to fused indolizidines and quinolizidines is disclosed. This method is conducted in mild conditions and shows well tolerance of functional groups. It is also easy to be scaled up to gram scale and can be applied smoothly to the total synthesis of alkaloids such as (±)-crispine A, (±)-xylopinine, (±)-desbromoarborescidine A, (±)-harmicine and other bioactive substances.

Tf2O/TTBP (2,4,6-Tri-tert-butylpyrimidine): An Alternative Amide Activation System for the Direct Transformations of Both Tertiary and Secondary Amides

Ten types of Tf2O/TTBP-mediated amide transformation reactions were investigated. The results showed that compared with pyridine derivatives 2,6-di-tert-butyl-4-methylpyridine (DTBMP) and 2-fluoropyridine (2-F-Pyr.), TTBP can serve as an alternative amide activation system for the direct transformation of both secondary and tertiary amides. For most surveyed examples, higher or comparable yields were generally obtained. In addition, Tf2O/TTBP combination was used to promote the condensation reactions of 2-(tert-butyldimethylsilyloxy)furan (TBSOF) with both tertiary and secondary amides, the one-pot reductive Bischler-Napieralski-type reaction of tertiary lactams, and Movassaghi and Hill's modern version of the Bischler-Napieralski reaction. The value of the Tf2O/TTBP-based methodology was further demonstrated by the concise and high-yielding syntheses of several natural products.

Synthetic method of tetrahydroisoquino ring compound and tetrahydro-beta-carbo ring compound

The invention provides a synthetic method of a tetrahydroisoquino ring compound and a tetrahydro-beta-carbo ring compound, and belongs to the technical field of synthesis. According to the method forsynthesizing the tetrahydroisoquino and the tetrahydro-b

N -Acyliminium Ion Chemistry: Improving the Access to Unsaturated γ-Lactams and Their N -α-Methoxylated Derivatives: Application to an Expeditive Synthesis of (±)-Crispine A

An improved synthesis of unsaturated γ-lactams by condensation of various primary amines with 2,5-dimethoxy-2,5-dihydrofuran is described. A modified mechanism for this reaction is suggested. Synthesis of their N -α-methoxylated derivatives, as N -acyliminium ion precursors, is also reported. Finally, a short synthesis of (±)-crispine A is presented as an illustrative application.

Dual Nicotinic Acetylcholine Receptor α4β2 Antagonists/α7 Agonists: Synthesis, Docking Studies, and Pharmacological Evaluation of Tetrahydroisoquinolines and Tetrahydroisoquinolinium Salts

We describe the synthesis of tetrahydroisoquinolines and tetrahydroisoquinolinium salts together with their pharmacological properties at various nicotinic acetylcholine receptors. In general, the compounds were α4β2 nAChR antagonists, with the tetrahydroisoquinolinium salts being more potent than the parent tetrahydroisoquinoline derivatives. The most potent α4β2 antagonist, 6c, exhibited submicromolar binding Ki and functional IC50 values and high selectivity for this receptor over the α4β4 and α3β4 nAChRs. Whereas the (S)-6c enantiomer was essentially inactive at α4β2, (R)-6c was a slightly more potent α4β2 antagonist than the reference β2-nAChR antagonist DHβη. The observation that the α4β2 activity resided exclusively in the (R)-enantiomer was in full agreement with docking studies. Several of tetrahydroisoquinolinium salts also displayed agonist activity at the α7 nAChR. Preliminary in vivo evaluation revealed antidepressant-like effects of both (R)-5c and (R)-6c in the mouse forced swim test, supporting the therapeutic potential of α4β2 nAChR antagonists for this indication.