What I Wish Everyone Knew About 1-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Diarylmethylamines are key intermediates and products in the pharmaceutical industry. Herein we disclose a novel method toward the synthesis of these important compounds via C-H functionalization. Presented is a reversible deprotonation of N-Boc benzylalkylamines at the benzylic C-H with in situ arylation by a NiXantPhos-based palladium catalyst (50-93 % yield, 29 examples). The method is also successful with N-Boc-tetrahydroisoquinolines. The advantages of this method are it avoids strong bases, low temperatures, and the need to transmetallate to main group metals for the coupling. Skipping steps! Diarylmethylamines are key intermediates and products in the pharmaceutical industry. A novel method toward the synthesis of these important compounds via C-H functionalization is reported. A reversible deprotonation of N-Boc benzylalkylamines at the benzylic C-H is coupled with in situ arylation with a (NiXantPhos)Pd-based catalyst (50-93 % yield, 29 examples). The advantages of this method are that it avoids strong bases, low temperatures, and the need to transmetallate to main group metals for the coupling.

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

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The synthesis of highly functionalised N-heterocycles has been achieved by the visible light mediated photoredox conversion of tertiary amines to azomethine ylides and their further reaction with maleimide derivatives as dipolarophiles. The Royal Society of Chemistry 2011.

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

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A solifenacin succinate-containing composition with less impurities which can be used as a bulk for pharmaceutical is provided. The solifenacin succinate-containing compostiion of the present invention has a reduced content of especially its optical isomers in comparison with the known compositions containing an acid addition salt of solifenacin, so that it can be used for production of a therapeutic agent containing solifenacin succinate. In addition, the above-described solifenacin succinate-containing composition can be easily produced in accordance with the production method of the present invention.

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

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A highly efficient sp3-sp3 carbon-carbon bond formation system was developed for the aerobic ruthenium-catalyzed oxidative cross-dehydrogenative coupling reaction between tertiary amines and sp3 C-H compounds in the presence of RuCl3/O2, thus giving the corresponding alpha-functionalized amines. Compared with the reported method, H2O2 or tBuOOH was replaced successfully by economical and facile oxygen as the oxidant. Three types of activated C-H bonds for pronucleophiles were evaluated in this system. All these features combined are in accordance with important prospective green chemistry aspects.

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

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Class III antiarrhythmic agents have been shown to prevent reentrant arrhythmias but also to be responsible for initiating arrhythmias characterised by afterdepolarizations and triggered activities. By combining potassium and calcium channel antagonistic actions, as with BRL-32872 (1), it might be possible to reduce the incidence of proarrhythmias albeit retaining antiarrhythmic efficacy. In the present study we synthesised and tested for their electrophysiological activity in guinea pig papillary muscle a wide panel of analogues of BRL-32872. Some qualitative relationships between compound structure and the inhibitory effect on the rapidly activating component of the delayed rectifier potassium current and/or the l-type calcium current will be presented. New derivatives depicting bell-shaped dose-response curves on action potential duration may therefore represent novel agents for improved antiarrhythmic therapy. Copyright (C) 1998 Elsevier Science Ltd.

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

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Research speed reading in 2021. Redox catalysis has been broadly utilized in electrochemical synthesis due to its kinetic advantages over direct electrolysis. An article , which mentions Reference of 3340-78-1, molecular formula is C15H15N. The compound – 2-Phenyl-1,2,3,4-tetrahydroisoquinoline played an important role in people’s production and life., Reference of 3340-78-1

For converting a homogeneous synthetic chemistry reaction to a heterogeneous one, using nanocatalysts, it is essential to investigate the underlying principles and the associated dominant factors of methodologies between inorganic nanoparticles and organic substrates. Here it is reported that novel, hydrothermally synthesized ruthenium (Ru) nanoparticles performed differently in molecular oxygen activation via single electron transfer for cross-dehydrogenative-coupling reactions, following a volcano shaped relationship between their oxidation levels and catalytic activity. Characterizations and a systematic mechanism study indicated that Ru3+ sites contributed to more superoxo- or peroxo-like species being formed from molecular oxygen on Ru nanoparticles with a moderate oxidation level, and the Ru3+ were the highly active species which accelerate this cross-dehydrogenative-coupling reaction via single electron transfer.

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

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H/D exchanges of arylmethyl amines and nitrogen heterocycles were conveniently achieved with KOt-Bu/DMSO-d6. The method is also applicable for phenyl benzyl ethers, diarylmethanes, and alkyl arenes. These H/D exchange reactions are suggested to proceed via a free radical pathway.

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

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In the continuing study directed toward the development of peroxisome proliferator-activated receptor gamma (hPPARgamma) agonist, we attempted to improve the water solubility of our previously developed hPPARgamma-selective agonist 3, which is insufficiently soluble for practical use, by employing two strategies: introducing substituents to reduce its molecular planarity and decreasing its hydrophobicity via replacement of the adamantyl group with a heteroaromatic ring. The first approach proved ineffective, but the second was productive. Here, we report the design and synthesis of a series of alpha-benzyl phenylpropanoic acid-type hPPARgamma partial agonists with improved aqueous solubility. Among them, we selected (R)-7j, which activates hPPARgamma to the extent of about 65% of the maximum observed with a full agonist, for further evaluation. The ligand-binding mode and the reason for the partial-agonistic activity are discussed based on X-ray-determined structure of the complex of hPPARgamma ligand-binding domain (LBD) and (R)-7j with previously reported ligand-LDB structures. Preliminal apoptotic effect of (R)-7j against human scirrhous gastric cancer cell line OCUM-2MD3 is also described.

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

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Enzymes dependent on nicotinamide cofactors are important components of the expanding range of asymmetric synthetic techniques. New challenges in asymmetric catalysis are arising in the field of deuterium labelling, where compounds bearing deuterium (2H) atoms at chiral centres are becoming increasingly desirable targets for pharmaceutical and analytical chemists. However, utilisation of NADH-dependent enzymes for 2H-labelling is not straightforward, owing to difficulties in supplying a suitably isotopically-labelled cofactor ([4-2H]-NADH). Here we report on a strategy that combines a clean reductant (H2) with a cheap source of 2H-atoms (2H2O) to generate and recycle [4-2H]-NADH. By coupling [4-2H]-NADH-recycling to an array of C=O, C=N, and C=C bond reductases, we demonstrate asymmetric deuteration across a range of organic molecules under ambient conditions with near-perfect chemo-, stereo- and isotopic selectivity. We demonstrate the synthetic utility of the system by applying it in the isolation of the heavy drug (1S,3?R)-[2?,2?,3?-2H3]-solifenacin fumarate on a preparative scale.

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

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The oxidative C-C bond formations between Csp3-H bond adjacent to nitrogen and Csp3-H bond of nitroalkanes are catalyzed efficiently by magnetically recoverable iron nanoparticles using oxygen. The catalyst can be magnetically removed and recycled easily for nine times without decreasing activity. Georg Thieme Verlag Stuttgart.

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