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Copper-Catalyzed Cyanomethylation of Substituted Tetrahydroisoquinolines with Acetonitrile

A novel method for the synthesis of cyanomethylated tetrahydroisoquinolines has been developed with mild reaction conditions, good yields and a broad substrate scope. Acetonitrile, a common solvent, is for the first time used as a pronucleophile for this type of two sp3C?H bonds cross-dehydrogenative coupling (CDC) reaction. A new oxidative system (CuCl2/TEMPO/Cs2CO3) has been established by our group, in which the mild TEMPO reagent was found to be a highly efficient oxidant. (Figure presented.).

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

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Substituted 2-[monoannelated (3,4-,4,5-, and 5,6-) pyridylalkylenesulfinyl]benzimidazoles

The present invention provides novel substituted 2-[monoannelated(3,4- 4,5-, and 5,6-)pyridylalkylenesulfinyl]-benzimidazoles with gastric acid inhibiting effects.

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

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Inhibition of [3H]dopamine uptake into striatal synaptosomes by isoquinoline derivatives structurally related to 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine.

Isoquinoline derivatives structurally related to 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) or 1-methyl-4-phenylpyridinium (MPP+) may be endogenous neurotoxins causing nigral cell death in Parkinson’s disease. These compounds inhibit mitochondrial function but, like MPP+, require accumulation in dopaminergic neurones via the dopamine reuptake system to exert toxicity. We, now, examine the substrate affinity of 14 neutral and quaternary isoquinoline derivatives (7 isoquinolines, 2 dihydroisoquinolines and 5 1,2,3,4-tetrahydroisoquinolines) for the dopamine reuptake system by their ability to inhibit the uptake of [3H]dopamine into rat striatal synaptosomes. Ten isoquinoline derivatives and MPP+ inhibited [3H]dopamine uptake in a concentration-dependent manner. Only 5 isoquinoline derivatives produced 50% inhibition of [3H]dopamine uptake (IC50 = 8.0-50.0 microM), none of which were as potent as MPP+ (IC50 = 0.33 microM). These findings suggest that isoquinoline derivatives are moderate to poor substrates for the dopamine reuptake system and that high concentrations of, or prolonged exposure to, isoquinoline derivatives may be necessary to cause neurodegeneration.

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

New explortion of 2-Methyl-1,2,3,4-tetrahydroisoquinoline

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A convenient synthesis of deuterium labeled amines and nitrogen heterocycles with KOt-Bu/DMSO-d6

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

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Improved simplicity and practicability in copper-catalyzed alkynylation of tetrahydroisoquinoline

Abstract: Alkynylation reactions of N-protected tetrahydroisoquinolines have been performed using several different protocols of cross dehydrogenative coupling. Initially, a CuCl-catalyzed method was investigated, which worked well with three different N-protecting groups, namely phenyl, PMP, and benzyl and t-BuOOH as oxidant in acetonitrile as solvent. The peroxide could then be replaced by simple air and acetonitrile for water, leading to an overall very environmentally friendly protocol. Finally, a decarboxylative alkynylation protocol starting from alkynoic acids was also developed using again air as oxidant. This avoids the use of gaseous alkynes in the introduction of short-chained alkyne substituents. Graphical abstract: [Figure not available: see fulltext.]

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

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Unexpected alkylation reaction of amines, acids and phenols by alkyl (triphenylphosphoranylidene)acetates

Reaction of methyl (triphenylphosphoranylidene)acetate in methanol with primary and secondary amines led to N-methylated derivatives. Similarly this mixture reacted with acids, phenol and phthalimide to afford methyl esters, anisole and N-methylphthalimide respectively. Treatment of ketolactam 2 by this mixture under high pressure activation gave the rearranged quinolinone 5.

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

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Tetrahydroisoquinolines. Part 2. Synthesis of 4-Substituted N-Methyl-1,2,3,4-tetrahydroisoquinolines via Regio- and Stereo-selective Elaboration of Tricarbonyl(N-methyl-1,2,3,4-tetrahydroisoquinoline)chromium

Thermolysis of hexacarbonylchromium with N-methyltetrahydroisoquinoline generates the tricarbonyl-(N-methyltetrahydroisoquinoline)chromium complex (4).The 4-exo proton of complex (4) can be regio- and stereo-selectively removed with butyl-lithium and replaced stereoselectivity with retention of configuration by a variety of electrophiles .Oxidative decomplexation generates quantitatively the corresponding 4-methyl, ethyl, benzyl, deuterio, phenyl, hydroxy, and (1-hydroxy-1-methylethyl)-N-methyltetrahydroisoquinolines.

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

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Benzylic functionalization of (eta6-alkylarene)chromium tricarbonyl complexes

A general method for the regioselective benzylic metallation of (eta6-alkylarene)chromium tricarbonyl complexes on the action of lithium amides in THF under very mild conditions has been developed. Transmetallation reactions of the lithium derivatives thus obtained produce the corresponding benzylic organotin, zinc and copper chromium tricarbonyl complexes. Methods for the preparative benzylic functionalization of (eta6-alkylarene)chromium tricarbonyl complexes have been developed, including carboxylation, alpha-hydroxyalkylation, gamma-carbonylation, acylation, arylation, vinylation, heteroarylation and alkylation procedures. 5-Acetoxy-3-benzyl-1,4-methano-2,3,4,5-tetrahydro-1H-3-benzazepine has been prepared using the benzylic lithium derivative of the (eta6-alkylarene)chromium tricarbonyl complex at the key step. This compound is a representative of the major class of physiologically active compounds known as C-norbenzomorphans.

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

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Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells

Methanolic extracts from the flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) were found to show inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the methanolic extracts, a new alkaloid, N-methylasimilobine N-oxide, was isolated together with eleven benzylisoquinoline alkaloids. The absolute stereostructure of the new alkaloid was determined from chemical and physicochemical evidence. Among the constituents isolated, nuciferine, N-methylasimilobine, (-)-lirinidine, and 2-hydroxy-1-methoxy-6a,7-dehydroaporphine showed potent inhibition of melanogenesis. Comparison of the inhibitory activities of synthetic related alkaloids facilitated characterization of the structure-activity relationships of aporphine- and benzylisoquinoline-type alkaloids. In addition, 3-30 muM nuciferine and N-methylasimilobine inhibited the expression of tyrosinase mRNA, 3-30 muM N-methylasimilobine inhibited the expression of TRP-1 mRNA, and 10-30 muM nuciferine inhibited the expression of TRP-2 mRNA.

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

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1612-65-3, Name is 2-Methyl-1,2,3,4-tetrahydroisoquinoline, belongs to tetrahydroisoquinoline compound, is a common compound. Quality Control of 2-Methyl-1,2,3,4-tetrahydroisoquinolineIn an article, once mentioned the new application about 1612-65-3.

Mild Reductive Cleavage of alpha-Aminoethers

1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methylisoquinoline (1) is converted by ethyl chloroformate (ECF)/NaBH3CN to 2--4,5-dimethoxytoluene (4) via the quaternary urethane 2.The same procedure leads from laudanosine (5) to the dibenzyl derivative 9.The reaction with ECF/NaBH3CN followed by LiAlH4 reduction is a versatile approach to Emde degradation products avoiding strongly basic conditions and elevated temperature.Cleavage reactions of other alpha-amino ethers, e.g. thebaine (18), and N-demethylation reactions of thetetrahydroisoquinolines 1 and 10 with ECF are reported.

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