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Determining the scope of the lanthanide mediated, sequential hydroamination/C-C cyclization reaction: Formation of tricyclic and tetracyclic aromatic nitrogen heterocycles

The scope of the lanthanide mediated, sequential hydroamination/C-C cyclization reaction was determined for the formation of tricyclic and tetracyclic aromatic nitrogen heterocycles. An array of ring sizes was explored to determine the diastereoselectivity. The electronic characteristics of the aromatic ring was also varied to determine how it affected the cascade reaction. It was found that the benzo[a]quinolizine and the pyrido[2,1,a]isoindolizine ring systems formed with the highest diastereoselectivity (>20:1), regardless of the electronic characteristics of the aromatic ring. Additionally, a tetracyclic indole nitrogen heterocycle was formed with a 2.3:1 diastereomeric ratio. A novel procedure for substrate preparation is also presented.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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Reusable, homogeneous water soluble photoredox catalyzed oxidative dehydrogenation of N-heterocycles in a biphasic system: Application to the synthesis of biologically active natural products

Herein, a simple and efficient method for the oxidative dehydrogenation (ODH) of tetrahydro-beta-carbolines, indolines and tetrahydro-(iso)quinolines is described using a reusable, homogeneous cobalt-phthalocyanine photoredox catalyst in a biphasic medium. A biphasic system offers an advantage of easy separation of the product and an efficient reusability of the homogeneous photoredox catalyst. Also, the current system significantly helps to overcome the solubility issue of the substrate and catalyst at room temperature. Its potential applications to organic transformations are demonstrated by the synthesis of various biologically active N-heterocycles such as indoles, (iso)quinolines and beta-carbolines and natural products such as eudistomin U, norharmane, and harmane and precursors to perlolyrine and flazin. Without isolation and purification, the catalyst solution can be reused up to 5 times with almost comparable reactivity. Furthermore, the efficiency of the reaction was demonstrated on a gram scale. To the best of our knowledge, this is the first report on ODH reactions using a non noble, reusable and homogeneous cobalt photoredox catalyst under environmentally friendly conditions.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Brief introduction of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline

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Construction of 1,3-Oxazolidines through a Three-Component [3+2] Cycloaddition of Tetrahydroisoquinolines, Aldehydes, and Ethyl Ketomalonate

A chemoselective and diastereoselective synthesis of fused oxazolidines was achieved by a three-component cascade reaction of tetrahydroisoquinolines (THIQs), alpha,beta-unsaturated aldehydes, and diethyl 2-oxomalonate. Probably due to the reactivity difference between the aldehyde and the ketone, the reaction proceeded through the condensation of THIQs with alpha,beta-unsaturated aldehydes and 1,3-dipolar cycloaddition of the generated azomethine ylide intermediate with 2-oxomalonate. The key features are easily available starting materials, mild reaction conditions, broad substrate scope, and high chemo- and diastereoselectivity.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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The influence of substitution at aromatic part of 1,2,3,4-tetrahydroisoquinoline on in vitro and in vivo 5-HT1A/5-HT2A receptor activities of its 1-adamantoyloaminoalkyl derivatives

Further structure-activity relationship (SAR) studies with the 1,2,3,4-tetrahydroisoquinoline (THIQ) class of 5-HT1A ligands led to the synthesis of new 1-adamantoyloaminoalkyl derivatives. The impact of substituent variations in the aromatic part of THIQ moiety on 5-HT1A and 5-HT2A receptor affinities, as well as in vivo functional properties of the investigated compounds were discussed. It was found that modification reduced the binding affinity for 5-HT1A receptors (in comparison with unsubstituted THIQ derivatives); however, the majority of new compounds still remained potent 5-HT1A ligands (Ki = 4.9-46 nM) and most of them showed features of partial agonists of postsynaptic 5-HT1A receptors. At the same time, their 5-HT2A receptor affinity was slightly increased (Ki = 40-1475 nM), which resulted in a loss of 5-HT2A/5-HT1A selectivity. 5-Br,8-OCH3 derivative – the most potent, mixed 5-HT1A/5-HT2A ligand – produced activation of presynaptic 5-HT1A receptors and showed properties of a 5-HT2A receptor antagonist. Copyright

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Extracurricular laboratory:new discovery of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline

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Visible light catalyzed Mannich reaction between: Tert -amines and silyl diazoenolates

The present work documents the alpha-C-H functionalization of tertiary amines via the visible light catalyzed Mannich reaction with silyl diazoenolates. The reaction takes place at room temperature with an organic dye, Rose Bengal, as a photocatalyst and oxygen as the oxidant. The resulting multifunctional products bearing an alpha-diazo-beta-keto group undergo Rh-carbenoid mediated cyclization, affording stable ammonium ylides in high yields.

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Reference£º
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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Silver-Catalyzed, Aldehyde-Induced alpha-C-H Functionalization of Tetrahydroisoquinolines with Concurrent C-P Bond Formation/N-Alkylation

(Chemical Equation Presented). The first facile and efficient silver-catalyzed, aldehyde-induced three-component reaction of N-unprotected tetrahydroisoquinolines, aldehydes, and dialkyl phosphonates has been developed, providing a general one-step approach to structurally diverse C1-phosphonylated THIQs accompanied by concurrent C-P bond formation/N-alkylation with remarkable functional group tolerance and excellent regioselectivity for endo products.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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Related Products of 1745-07-9, Because a catalyst decreases the height of the energy barrier, its presence increases the reaction rates of both the forward and the reverse reactions by the same amount.1745-07-9, Name is 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline, molecular formula is C11H15NO2. In a article£¬once mentioned of 1745-07-9

Fluorescent and Biocompatible Ruthenium-Coordinated Oligo(p-phenylenevinylene) Nanocatalysts for Transfer Hydrogenation in the Mitochondria of Living Cells

It is challenging to design metal catalysts for in situ transformation of endogenous biomolecules with good performance inside living cells. Herein, we report a multifunctional metal catalyst, ruthenium-coordinated oligo(p-phenylenevinylene) (OPV-Ru), for intracellular catalysis of transfer hydrogenation of nicotinamide adenine dinucleotide (NAD+) to its reduced format (NADH). Owing to its amphiphilic characteristic, OPV-Ru possesses good self-assembly capability in water to form nanoparticles through hydrophobic interaction and pi?pi stacking, and numerous positive charges on the surface of nanoparticles displayed a strong electrostatic interaction with negatively charged substrate molecules, creating a local microenvironment for enhancing the catalysis efficiency in comparison to dispersed catalytic center molecule (TOF value was enhanced by about 15 fold). OPV-Ru could selectively accumulate in the mitochondria of living cells. Benefiting from its inherent fluorescence, the dynamic distribution in cells and uptake behavior of OPV-Ru could be visualized under fluorescence microscopy. This work represents the first demonstration of a multifunctional organometallic complex catalyzing natural hydrogenation transformation in specific subcellular compartments of living cells with excellent performance, fluorescent imaging ability, specific mitochondria targeting and good chemoselectivity with high catalysis efficiency.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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METHOD OF PREPARING TETRABENAZINE AND DIHYDROTETRABENAZINE

The present invention relates to a method for preparing tetrabenazine (TBZ) and dihydrotetrabenazine (DTBZ), and more specifically to a method for preparing tetrabenazine (TBZ) and dihydrotetrabenazine (DTBZ) by using simple and short reaction processes of using 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline and 4-methyl-2-(3-(trimethylsilyl)prop-1-ene-2-yl)pentane as starting materials to sequentially perform an alkylation reaction, an Aza-Prins cyclization reaction in the presence of an oxidant and an oxidation reaction.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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Rearrangements of 1,6,7-Trisubstituted 2-Methyl-1,2,3,4-tetrahydroisoquinolinium 2-Methylides

Chemical behavior of 1,6,7-trisubstituted 2-methy-1,2,3,4-tetrahydroisoquinolinium 2-methylides 4 was investigated in fluoride-ion induced desilation reaction of 1,6,7-trisubstituted 2-methyl-2-(trimethylsilyl)methyl-1,2,3,4-tetrahydroisoquinolinium iodides 3.The 1-nonsubstituted (4a,b) and 1-alkyl-substituted ylides (4c,d) gave mixtures of five products (7-11), but the 1-phenyl-substituted analogues (4e,f) yielded (E)- and (Z)-2,3-disubstituted 5-benzylidene-1,3-cyclohexadiene-6-spiro-3′-1′-methylpyrrolidines (E)-5 and (Z)-5 and 7,8-disubstituted 3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines 6.The mechanisms of the rearrangement are discussed.

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Reference£º
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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18F-Labeled indole-based analogs as highly selective radioligands for imaging sigma-2 receptors in the brain

We have designed and synthesized a series of indole-based sigma2 receptor ligands containing 5,6-dimethoxyisoindoline or 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline as pharmacophore. In vitro competition binding assays showed that all ten ligands possessed low nanomolar affinity (Ki?=?1.79?5.23?nM) for sigma2 receptors and high subtype selectivity (Ki (sigma2)/Ki (sigma1)?=?56?708). Moreover, they showed high selectivity for sigma2 receptor over the vesicular acetylcholine transporter (>1000-fold). The corresponding radiotracers [18F]16 and [18F]21 were prepared by an efficient one-pot, two-step reaction sequence with a home-made automated synthesis module, with 10?15% radiochemical yield and radiochemical purity of >99%. Both radiotracers showed high brain uptake and sigma2 receptor binding specificity in mice.

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Reference£º
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem