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Bifunctional iron complexes: Efficient catalysts for C=O and C=N reduction in water

The application of bifunctional iron complexes for the hydrogenation of polarized C=X bonds is reported. Two modified Knoelker complexes bearing ionic fragments were synthesized and fully characterized. With these well-defined complexes, the reaction proceeded under mild conditions in pure water, and various alcohols and amines were isolated in good yields. Compared with hydrogenation in organic solvents, better reactivities were observed. Is this the iron age? Well-defined iron-complex-catalyzed reduction of aldehydes, ketones, and imines using molecular hydrogen in water is presented. Under mild conditions, good yields for a broad range of substrates are achieved.

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

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Ferritin encapsulation of artificial metalloenzymes: Engineering a tertiary coordination sphere for an artificial transfer hydrogenase

Ferritin, a naturally occuring iron-storage protein, plays an important role in nanoengineering and biomedical applications. Upon iron removal, apoferritin was shown to allow the encapsulation of an artificial transfer hydrogenase (ATHase) based on the streptavidin-biotin technology. The third coordination sphere, provided by ferritin, significantly influences the catalytic activity of an ATHase for the reduction of cyclic imines.

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

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Isoquinoline-N-Boranes as Precursors to Substituted Tetrahydroisoquinolines

A new approach to the syntheses of 1,2-disubstituted 1,2,3,4-tetrahydroisoquinolines from isoquinoline-N-boranes is described.The method is a “one-pot” operation in which substituents are introduced consecutively as electrophiles and nucleophiles with accompanying reduction of the heterocyclic ring.This procedure differs from the classical ones in that both requisite rings are present in the starting material and thus avoids the inefficient cyclizations of phenethylamine derivatives when unactivated substrates would be required.The synthetic utility of this process is demonstrated with several examples including the alkaloids carnegine and hydrohydrastinine.

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

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A succinic acid Solley that new raw materials of synthesizing process (by machine translation)

The invention discloses a succinic acid thorley that new raw materials of synthesizing process, respectively in order to 2 – phenethylamine and 3 – synthesizing hydrochloride as the starting material synthetic fragment A, fragment B, the occurrence of the condensation reaction produced Solley that new, by succinic acid and get thorley that new, characterized in that using straight chain paraffins and water is used as the reaction solvent, alkali metal hydroxide or carbonate, hydrogencarbonate for capture, phenethylamine takes acylation reaction with benzoyl chloride is not soluble in the reaction solvent of solid precipitation fragment A intermediate 1, after treatment directly during the filtering; fragment A isomer, using dimethyl sulfoxide as solvent, alkali metal hydroxide catalytic racemic, the by-product isomer can be recycled; fragment of B 2nd step treatment after the reaction, the conventional vacuum distillation method to obtain a high purity, high yield of 3 – acetoxy quinine acetic acid salt, the invention provides a high yield, is suitable for industrial mass production, economic and environmental protection new synthesis process. (by machine translation)

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

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PROCESSES FOR THE PREPARATION OF SOLIFENACIN OR A SALT THEREOF

The present invention describes recovery and racemization of (1R)-Phenyl- 1,2,3,4-tetrahydroisoquinoline of compound of formula (III) to obtain racemic 1- phenyl-1, 2,3,4-tetrahydroisoquinoline of compound of formula (I) and its further resolution to get ( IS)-1-phenyl-1, 2, 3, 4-tetrahydroisoquinoline (intermediate B) in high chemical and chiral purity, which is the key intermediate for the preparation of (3R)-azabicyclo[2.2.2]oct-3-yl (1S)-1-phenyl-3,4-dihydroisoquinoline-2-(1H)- carboxylate.

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

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3,4-DIHYDROISOQUINOLINE COMPONDS AS MUSCRINIC RECEPTOR ANTAGONISTS FOR THE TREATMENT OF RESPIRATORY, URINARY AND GASTROINTESTINAL DISEASES

The present invention generally relates to muscarinic receptor antagonists of formula (I), which are useful, among other uses, for the treatment of various diseases of the respiratory, urinary and gastrointestinal systems mediated through muscarinic receptors. The invention also relates to the process for the preparation of disclosed compounds, pharmaceutical compositions containing the disclosed compounds, and the methods for treating diseases mediated through muscarinic receptors. Formula (I) wherein Formula (II) represents a nitrogen-containing ring having from 5 to 9 carbon atoms is a bridging group selected from the group consisting of-(CH2)n-,-CH(Q)CH2-,-CH2 CH(Q)CH2-,-CH2-O-CH2-or-CH2-NH-CH2-), where n is an integer selected from 0-3 (wherein when n is zero then T represents a direct bond); Y is alkylene, alkenylene, alkynylene or no atom; X is-NH or oxygen.

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

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Antiimplantation Agents: Part II – 1,2-Diaryl-1,2,3,4-tetrahydroisoquinolines

1,2-Diaryl-3,4-dihydroisoquinolinium derivatives (5) have been synthesised from N-aryl-N-aroyl-beta-phenethylamines (4) and found to exhibit no antiimplantation activity in the rat whereas many of the corresponding tetrahydroisoquinolines (6) are active.Structure-activity relationships have also been studied. 1-(p-Fluorophenyl)-6-methoxy-2-phenyl-1,2,3,4-tetrahydroisoquinoline (6u) and its nor derivative (6v) are very potent, while the ortho (6g) and the meta (6n) fluoro analogues as well as the des-fluoro derivative (6d) are quite active.Extensive biological tests have been carried out on 6g.The enantiomers (+)-6p*HCl and (-)-6q*HCl of 6n have similar activity profiles as that of 6n showing no separation of antiimplantation and estrogenic properties.Diastereomeric 2-(2-methyl-2-phenethyl)-1-phenyl-1,2,3,4-tetrahydroisoquinolines (13a and 13b) show similar properties, while the tetracyclic derivative 19 is inactive. 2-Phenoxyethyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline (26) shows moderate activity, but 1-(beta-phenethyl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline 29 is inactive.

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

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Redox-Annulation of Cyclic Amines and beta-Ketoaldehydes

Benzo[a]quinolizine-2-one derivatives are readily assembled from 1,2,3,4-tetrahydroisoquinoline and beta-ketoaldehydes by means of a new intramolecular redox-Mannich process. These reactions are promoted by simple acetic acid and are thought to involve azomethine ylides as reactive intermediates.

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

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Redox-Annulations of Cyclic Amines with ortho-Cyanomethylbenzaldehydes

Amines such as 1,2,3,4-tetrahydroisoquinoline undergo redox-neutral annulations with ortho-cyanomethylbenzaldehydes. These amine alpha-C-H bond functionalization reactions are promoted by acetic acid. The resulting beta-aminonitriles can be converted to the corresponding beta-aminoalcohols in diastereoselective fashion.

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

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Noncompetitive NMDA Antagonists: A novel synthesis of 1-phenyltetrahydro-3-benzazepines

The key step in the synthesis of the pharmacologically interesting l-phenyltetrahydro-3-benzazepine skeleton is the Michael addition of (2-lithiophenyl)acetaldehyde acetals, which are generated in situ upon treatment of the bromo acetals 5a,b with n-butyllithium, to beta-nitrostyrene (6). The reductive ring closure of the nitro acetals 7a,b succeeded with zinc dust and hydrochloric acid to give the 3-benzazepines 11a,b in good yields. The unsubstituted 3-benzazepine 11a showed a considerable affinity for the phencyclidine binding site of the NMDA receptor (K(i) = 6.41 muM), whereas donor substituents in the aryl moiety (11b,c) reduce the affinity for the NMDA receptor.

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