Archives for Chemistry Experiments of 2-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Oxidative Difluoromethylation of Tetrahydroisoquinolines Using TMSCF2SPh: Synthesis of Fluorinated Pyrrolo[2,1-a]isoquinolines and Benzo[a]quinolizidines

An efficient C1-difluoromethylation of tetrahydroisoquinolenes was achieved using TMSCF2SPh as a difluoromethylating agent and 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (TEMPO+BF4-) as an oxidant. The process provides an access to a variety of C1-difluoro(phenylsulfanyl)methylated tetrahydroisoquinoline adducts in good yields. These adducts were employed as key precursors for preparing fluorinated pyrrolo[2,1-a]isoquinoline and benzo[a]quinolizidines.

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

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Visible-Light-Driven Palladium-Catalyzed Radical Alkylation of C?H Bonds with Unactivated Alkyl Bromides

Reported herein is a novel visible-light photoredox system with Pd(PPh3)4 as the sole catalyst for the realization of the first direct cross-coupling of C(sp3)?H bonds in N-aryl tetrahydroisoquinolines with unactivated alkyl bromides. Moreover, intra- and intermolecular alkylations of heteroarenes were also developed under mild reaction conditions. A variety of tertiary, secondary, and primary alkyl bromides undergo reaction to generate C(sp3)?C(sp3) and C(sp2)?C(sp3) bonds in moderate to excellent yields. These redox-neutral reactions feature broad substrate scope (>60 examples), good functional-group tolerance, and facile generation of quaternary centers. Mechanistic studies indicate that the simple palladium complex acts as the visible-light photocatalyst and radicals are involved in the process.

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

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Photoredox catalysis under shear using thin film vortex microfluidics

A microfluidic vortex fluidic device (VFD) operating in either confined or continuous mode is effective in high yielding photoredox reactions involving Rose Bengal, with short reaction times. This processing can be translated to multi-components reactions, also with significantly reduced processing times relative to batch processing and channel microfluidic processing, with comparable or improved yields.

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

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Proline metabolism in cell regulation and cancer biology: Recent advances and hypotheses

Significance: It is increasingly clear that proline metabolism plays an important role in metabolic reprogramming, not only in cancer but also in related fields such as aging, senescence, and development. Although first focused on proline catabolism, recent studies from a number of laboratories have emphasized the regulatory effects of proline synthesis and proline cycling. Recent Advances: Although proline dehydrogenase/proline oxidase (PRODH/POX) has been known as a tumor protein 53 (P53)-activated source of redox signaling for initiating apoptosis and autophagy, senescence has been added to the responses. On the biosynthetic side, two well-recognized oncogenes, c-MYC and phosphoinositide 3-kinase (PI3K), markedly upregulate enzymes of proline synthesis; mechanisms affected include augmented redox cycling and maintenance of pyridine nucleotides. The reprogramming has been shown to shift in clonogenesis and/or metastasis. Critical Issues: Although PRODH/POX generates reactive oxygen species (ROS) for signaling, the cellular endpoint is variable and dependent on metabolic context; the switches for these responses remain unknown. On the synthetic side, the enzymes require more complete characterization in various cancers, and demonstration of coupling of proline metabolites to other pathways may require studies of protein-protein interactions, membrane transporters, and shuttles. Future Directions: The proline metabolic axis can serve as a scaffold on which a variety of regulatory mechanisms are integrated. Once understood as a central mechanism in cancer metabolism, proline metabolism may be a good target for adjunctive cancer therapy.

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

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Iodo-Bodipys as visible-light-absorbing dual-functional photoredox catalysts for preparation of highly functionalized organic compounds by formation of C-C bonds via reductive and oxidative quenching catalytic mechanisms

Iodo-Bodipys were used as organic catalysts for three different photoredox catalytic organic reactions, i.e. the aza-Henry reaction of tetrahydroisoquinoline, oxidation/[3 + 2] cycloaddition/oxidative aromatization tandem reaction between tetrahydroisoquinolines and maleimides, and C-H arylation of heteroarenes with diazonium salts. The organic photocatalysts act as either electron acceptors (reductive quenching) or electron donors (oxidative quenching) in the single electron transfer (SET) of the catalytic cycles. Different from the widely used Ru(bpy)3[PF6]2, Ir(ppy)3, or halo-xanthane photocatalysts (Eosin Y or Rose Bengal), the new organic photocatalysts show strong absorption of visible light and long-lived triplet excited states, which are beneficial for SET, a crucial step for photoredox catalytic organic reactions. Moreover, the molecular structures of the new photocatalysts can be easily modified, as a result the absorption wavelength of the photocatalysts was readily tuned from 529 nm to 630 nm. The three different types of organic reactions are accelerated with the new organic photocatalysts (typical reaction times 1-2 h) compared to that catalyzed by Ru(bpy)3[PF6]2 or Ir(ppy)3 (reaction time: 12-72 h). The C-H arylation of thiophene with phenyl diazonium salts was used to prepare new Bodipy derivatives that show large Stokes shift. Our results are useful for designing of new organic catalysts for photoredox catalytic organic reactions to prepare highly functionalize organic compounds.

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

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SELECTIVE REDUCTION of 2-CARBAMOYL-1-PHENYL-1,4-DIHYDROISOQUINOLIN-3(2H)-ONES

Treatment of 2-carbamoyl-1-phenyl-1,4-dihydroisoquinolin-3(2H)-ones (1) with lithium aluminium hydride or diborane resulted always in the reduction of the ring carbonyl group and, depending on the nature of the reducing agent and the structure of the starting compound 1,2,3,4-tetrahydro- (2), 1,2-dihydroisoquinoline derivatives (3) or 1,2,3,4-tetrahydroisoquinolin-3-ols (5) were obtained.

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

The Absolute Best Science Experiment for (S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Enantioselective and rapid Rh-catalyzed arylation of N -tosyl- and N -nosylaldimines in methanol

Enantiomerically enriched tosyl-protected diarylmethylamines were rapidly prepared by the asymmetric addition of arylboronic acids to N-tosylaldimines under mild conditions in the presence of a catalyst prepared in situ from Rh(I) and a chiral diene ligand. This methodology offers access to diarylmethylamines in good yields with excellent chiral purity at room temperature using MeOH as a solvent and NEt3 as a base. Its synthetic utility was demonstrated by the preparation of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (14), an antagonist of the N-methyl-d-aspartate (NMDA) receptor.

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

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Identification of an Imine Reductase for Asymmetric Reduction of Bulky Dihydroisoquinolines

A new imine reductase from Stackebrandtia nassauensis (SnIR) was identified, which displayed over 25- to 1400-fold greater catalytic efficiency for 1-methyl-3,4-dihydroisoquinoline (1-Me DHIQ) compared to other imine reductases reported. Subsequently, an efficient SnIR-catalyzed process was developed by simply optimizing the amount of cosolvent, and up to 15 g L-1 1-Me DHIQ was converted completely without a feeding strategy. Furthermore, the reaction proceeded well for a panel of dihydroisoquinolines, affording the corresponding tetrahydroisoquinolines (mostly in S-configuration) in good yields (up to 81%) and with moderate to excellent enantioselectivities (up to 99% ee).

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

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Cobalt(II)-Catalyzed N-Acylation of Amines through a Transamidation Reaction

A practical protocol has been developed for a Co(OAc)2¡¤4H2O-catalyzed transamidation reaction. The reaction gives high yields and uses N,N-dimethylformamide and other amides as carbonyl sources. The protocol is rapid and simple, and it does not require any acids, bases, ligands, or other additives. It works well for a wide range of primary, secondary, and heterocyclic amines.

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

New explortion of 7-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride

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COMPOUNDS FOR TREATMENT OF NEURODEGENERATIVE DISEASES

The present invention relates to a class of small molecule hydroxamic acid compounds capable of inhibiting histone deacetylases (HDACs). The present invention also relates to methods of preparation of hydroxamic acid HDAC inhibitor compounds of the invention, which are N-substituted-1,2,3,4-tetrahydroisoquinoline hydroxamic acid derivatives, and their incorporation into pharmaceutical compositions and methods of administration. The present invention also relates to N-substituted-1,2,3,4-tetrahydroisoquinoline hydroxamic acid derivatives, which may be prepared as a hydroxamic acid HDAC inhibitor compound library that can be utilized in screening methods known in the art.

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