Top Picks: new discover of 1-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Integrating Hydrogen Production with Aqueous Selective Semi-Dehydrogenation of Tetrahydroisoquinolines over a Ni2P Bifunctional Electrode

Exploring an alternative anodic reaction to produce value-added chemicals with high selectivity, especially integrated with promoted hydrogen generation, is desirable. Herein, a selective semi-dehydrogenation of tetrahydroisoquinolines (THIQs) is demonstrated to replace the oxygen evolution reaction (OER) for boosting H2 evolution reaction (HER) in water over a Ni2P nanosheet electrode. The value-added semi-dehydrogenation products, dihydroisoquinolines (DHIQs), can be selectively obtained with high yields at the anode. The controllable semi-dehydrogenation is attributed to the in situ formed NiII/NiIII redox active species. Such a strategy can deliver a variety of DHIQs bearing electron-withdrawing/donating groups in good yields and excellent selectivities, and can be applied to gram-scale synthesis. A two-electrode Ni2P bifunctional electrolyzer can produce both H2 and DHIQs with robust stability and high Faradaic efficiencies at a much lower cell voltage than that of overall water splitting.

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

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Structural elaboration of dicyanopyrazine: Towards push-pull molecules with tailored photoredox activity

As an extension of the successful dicyanopyrazine photoredox catalysts, a series of X-shaped push-pull molecules with a systematically altered structure were designed and facilely synthesized; their structure-property relationship was elucidated in detail via experimental as well as theoretical calculations. Dicyanopyrazines are proven to be powerful photoredox catalysts with a push-pull arrangement that allows facile property tuning by interchanging a particular part of the D-pi-A system. Changing the mutual position of the cyano acceptors and the methoxy, methylthio and thienyl donors as well as modifying the linker allowed wide tuning of the fundamental properties of the catalysts. Contrary to the currently available organic photoredox catalysts, we provided a series of catalysts based on a pyrazine heterocyclic scaffold with easy synthesis and further modification, diverse photoredox characteristics and wide application potential across modern photoredox transformations. The photoredox catalytic activities of the target catalysts were examined in a benchmark cross-dehydrogenative coupling and novel and challenging annulation reactions.

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

More research is needed about 166591-85-1

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A new strategy for accessing (S)-1-(furan-2-yl)pent-4-en-1-ol: a key precursor of Ipomoeassin family of compounds and C1?C15 domain of halichondrins

A highly efficient synthesis of (S)-1-(furan-2-yl)pent-4-en-1-ol, known to be an initial precursor of Ipomoeassin family of compounds and C1?C15 domain of halichondrins has been achieved via a sequence involving the use of Weinreb amide formation followed by Weinreb ketone synthesis and finally CBS (Corey?Bakshi?Shibata) reduction. Detailed study on improvement of each step is described. The title compound was converted to a potential cytotoxic agent for further pharmacological studies.

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

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Processes for optical resolution of 1-phenyl-1,2,3,4-tetrahydroisoquinoline

Optically pure 1(S)-phenyl-1,2,3,4-tetrahydroisoquinoline tartrate is prepared. The 1(S)-phenyl-1,2,3,4-tetrahydroisoquinoline tartrate is particularly useful for preparing solifenacin succinate.

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

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Novel N-substituted tetrahydroisoquinoline/isoindoline hydroxamic acid compounds

Compounds of a certain formula I, wherein R1, R2, R3, X, Y, r, s, t, u and v have the meanings as defined in the specification, and the salts, solvates and hydrates thereof are novel effective HDAC 6 inhibitors

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

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Synthesis and antibacterial activities of N-substituted-glycinyl 1 H-1,2,3-triazolyl oxazolidinones

A series of 1H-1,2,3-triazolyl piperazino oxazolidinone analogs with optionally varied glycinyl substitutions were synthesized and their antibacterial activity assessed against a panel of susceptible and resistant Gram-positive and selected Gram-negative bacteria including clinical isolates. The N-aroyl-and N-heteroaroyl-glycinyl (MIC: 0.06-4 mug/ml) derivatives were more potent than the N-acylglycinyl (2-8 mug/ml) derivatives against all Gram-positive bacteria tested. Nitro substitution on aryl and heteroaryl rings significantly enhanced activity against Gram-positive bacteria, as noted with the 3,5-dinitrobenzoyl (6m and 6n) and 5-nitro-2-furoyl (6u and 6v) derivatives with MIC ranges of and 0.25-0.5 and 0.06-0.5 mug/ml, respectively. These nitro analogs also showed more potent extended activity against Moraxella catarrhalis, with MICs ranges of 0.25-1 mug/ml, compared to linezolid (MIC: 8 mug/ml). Hence, the presence of the N-aroyl and/or N-heteroaroyl glycinyl structural motifs as spacer group could significantly enhance the antibacterial activities of 1H-1,2,3-triazolyl oxazolidinone class of compounds.

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

A new application about 2-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Exploiting single-electron transfer in Lewis pairs for catalytic bond-forming reactions

A single-electron transfer (SET) between tris(pentafluorophenyl)borane (B(C6F5)3) andN,N-dialkylanilines is reported, which is operativeviathe formation of an electron donor-acceptor (EDA) complex involving pi-orbital interactions as a key intermediate under dark conditions or visible-light irradiation depending on the structure of the aniline derivatives. This inherent SET in the Lewis pairs initiates the generation of the corresponding alpha-aminoalkyl radicals and their additions to electron-deficient olefins, revealing the ability of B(C6F5)3to act as an effective one-electron redox catalyst.

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

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HETEROCYCLES FROM NITRILE IMINES. PART IV. CHIRAL 4,5-DIHYDRO-1,2,4-TRIAZIN-6-ONES

The reaction of nitrile imines (II) with alpha-amino esters (III) proceeds with no detectable racemization and constitutes a convenient synthetic route to 4,5-dihydro-1,2,4-triazin-6-ones (IV).Permangamate oxidation of heterocycles (IV) affords the corresponding 1,2,4-triazin-6-ones (V).The reaction of (II) with beta-amino esters gives the respective acyclic amidrazone adducts (VI).

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

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Discovery of brain penetrant, soluble, pyrazole amide EP1 receptor antagonists

We describe the discovery of a series of pyrazole amide EP1 receptor antagonists with good aqueous solubility and CNS penetration. In order to achieve solubility we investigated the incorporation of a basic group in the region of the molecule previously occupied by a carboxylic acid, which was known to be a key element of the pharmacophore. This study led to the identification of compounds such as 4h, 4j and 10b which demonstrated brain-to-blood ratios of 0.8:1-2.0:1 in addition to good solubility and metabolic stability.

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

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1-SUBSTITUTED TETRAHYDROISOQUINOLINE COMPOUND

Provided is a compound useful as an N-type Ca2+ channel blocker. As a result of intensive studies of compounds having an action of blocking N-type Ca2+ channels, the present inventors found that a tetrahydroisoquinoline compound of the present invention having a substituent at the 1-position has an action of blocking the N-type Ca2+ channels, an antinociceptive pain action, an antineuropathic pain action, an abdominal pain-inhibitory action and an opioid-induced constipation-improving action, and the present invention has been completed based on these findings. The compound of the present invention can be used as a pharmaceutical composition for preventing and/or treating various pains such as neuropathic pain and nociceptive pain, headaches such as migraine and cluster headache, central nervous system diseases such as anxiety, depression, epilepsy, cerebral stroke and restless legs syndrome, abdominal symptoms such as abdominal pain and abdominal distension, stool abnormalities such as diarrhea and constipation, digestive system diseases such as irritable bowel syndrome, urinary system diseases such as overactive bladder and interstitial cystitis, etc.

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