3230-65-7

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dihydroisoquinoline is used as a reagent in the preparation of 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides, which are antiproliferative tubulin inhibitors. These compounds have potential applications in the development of anticancer drugs.
Used in Organic Synthesis:
3,4-Dihydroisoquinoline can be used as a reactant to synthesize various organic compounds, such as:
5,6-Dihydro-8H-isoquino[1,2-b]quinazolin-8-one: 3,4-DIHYDROISOQUINOLINE is synthesized through a decarboxylative cyclization reaction with isatoic anhydride using tetrabutylammonium iodide (TBAI) as a catalyst.
1-naphtholyl tetrahydroisoquinoline: 3,4-DIHYDROISOQUINOLINE is synthesized through an aza-Friedel-Crafts reaction with various naphthols, which can be used in the development of organic dyes and pigments.
3,4-dihydroisoquinoline pseudo bases: These are employed as starting materials for the preparation of 3-benzazepine derivatives, which have potential applications in the synthesis of pharmaceutical compounds and other organic molecules.

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 6567, 1994 DOI: 10.1016/S0040-4039(00)78274-8

InChI:InChI=1/C9H9N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-4,7H,5-6H2

Upstream product

• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 23069-99-0 N-(2-phenylethyl)formamide 
• 60355-20-6 2'-(2-chloroethyl)benzaldehyde 
• 22901-09-3 2-(2-bromoethyl)benzaldehyde 
• 42429-63-0 3,4-dihydroisoquinoline 1,2-oxide 
• 75-18-3 dimethylsulfide 
• 598-26-5 dimethylketene 
• 24423-87-8 3,4-dihydro-isoquinoline 2-oxide 
• 54105-63-4 1,2,3,4-tetrahydroisoquinolin-2-ol 
• 2079-11-0 N-allyl 1,2,3,4-tetrahydroisoquinoline 
• 100-68-5 methyl-phenyl-thioether 
• 139-66-2 diphenyl sulfide 
• 1822-73-7 phenylthioethylene 
• 64-17-5 ethanol 

Downstream Products

• 22990-19-8 1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 116956-99-1 2-(2,4-dinitro-phenyl)-3,4-dihydro-isoquinolinium; chloride . compound with 3,4-dihydro-isoquinoline 
• 10166-05-9 4-benzylisoquinoline 
• 119-65-3 isoquinoline 
• 62541-59-7 7-nitro-3,4-dihydroisoquinoline 
• 66610-76-2 3-(2,2,6,6-tetramethyl-cyclohexylidene)-6,10b-dihydro-5H-[1,2,4]oxathiazolo[5,4-a]isoquinoline 
• 37760-44-4 3-phenyl-6,10b-dihydro-5H-[1,2,4]oxadiazolo[5,4-a]isoquinoline 
• 129818-76-4 1-(3-hydroxy-2-cyclohexen-1-on-2-yl)-2-acetyl-1,2,3,4-tetrahydroisoquinoline 
• 110254-47-2 1-Diacetylmethyl-2,3-diphenyl-5,6-dihydropyrrolo<2.1-a>isochinolin 
• 74156-45-9 2-(2-Chloromethyl-benzoyl)-1,2,3,4-tetrahydro-isoquinoline-1-carbonitrile 
• 105400-81-5 2-(1,2,3,4-tetrahydro-1-isoquinolinyl)acetic acid 
• 1424-84-6 1-(ethoxycarbonylmethyl)-1,2,3,4-tetrahydroisoquinoline 
• 90136-99-5 4-(p-hydroxybenzyl)-isoquinoline 
• 90136-93-9 4-(o-hydroxybenzyl)-isoquinoline 

Relevant academic research and scientific papers

A one-pot catalyst/external oxidant/solvent-free cascade approach to pyrimidines: Via a 1,5-hydride transfer

A cascade 3-component reaction of 6-aminouracil, aldehyde and tetrahydroisoquinolines under heating in the absence of catalyst, external oxidant and solvent is performed. The reaction constructs a new pyrimidine ring by the functionalization of the C-H bond adjacent to nitrogen through a 1,5-hydride shift. No chromatographic techniques were required to purify the products.

OXIDATION OF 1,2,3,4-TETRAHYDROISOQUINOLINES TO 3,4-DIHYDROISOQUINOLINES WITH MOLECULAR OXYGEN CATALYZED BY COPPER(II) CHLORIDE

A catalytic oxidation system, a CuCl2-O2 system, was efficient for dehydrogenation of 1,2,3,4-tetrahydroisoquinolines to 3,4-dihydroquinolines.Oxidation of 1,2,3,4-tetrahydroquinoline was also carried out.

Investigation of the regio- and stereoselectivity of the annelation reaction of cyclic Schiff base with structurally asymmetrical β,β′-triketones. Synthesis and properties of 17-acetoxy-8-aza-D-Homogona-12,17a-diones

Annelation ([2+4]-cyclocondensation) of 3,4-dihydroixoquinolines and 2-acetyl-4-acetoxycyclohexane-1,3-dione gives 17-acetoxy-8-aza-D-homogona-12,17a-diones as a mixture of the C(9), C(17)-stereoisomers with the (9R, 17S: 9S, 17R) racemic pair predominating.

Visible-Light/Photoredox-Mediated sp3 C-H Functionalization and Coupling of Secondary Amines with Vinyl Azides in Flow Microreactors

Structurally diverse imidazole derivatives were synthesized by a visible-light/[Ru(bpy)3][(PF6)2]-mediated coupling of vinyl azides and secondary amines in flow microreactors. This operationally simple and atom-economical

Stereochemistry and Mechanistic Insight in the [2k+2i+2i] Annulations of Ketenes and Imines

The stereochemistry and mechanistic insight in the annulations of one ketene molecule with two imine molecules ([2k+2i+2i] annulation) are studied by using six-membered 3,4-dihydroisoquinoline as an imine probe. A concerted hetero-Diels-Alder cycloaddition mechanism is proposed to explain the stereochemical outcomes. In most cases, the zwitterionic 2-aza-1,3-butadiene-type intermediates, generated from ketenes and imines, undergo endo hetero-Diels-Alder cycloaddition with the second imine molecule. For ketenes with electron-donating substituents, (2,4)-cis-(4,5)-cis-[2k+2i+2i] annuladducts formed stereospecifically, while, for ketenes with electron-accepting substituents, (2,4)-cis-(4,5)-trans-[2k+2i+2i] annuladducts are generated stereospecifically. The [2k+2i+2i] annulations of aryloxyketenes and 3,4-dihydroisoquinoline give stereodivergent products due to the occurrence of the stepwise nucleophilic annulation. However, in the [2k+2i+2i] annulations of seven-membered cyclic imine dibenzo[b,f][1,4]oxazepine, the zwitterionic aza-butadiene-type intermediates exclusively undergo exo hetero-Diels-Alder cycloadditions with another molecule of imine to yield (2,4)-trans-(4,5)-trans-[2k+2i+2i] annuladducts stereospecifically, regardless of the ketene substituents. The mechanistic model not only discloses the nature of the [2k+2i+2i] annulations, but also can be used to explain and predict the stereochemistry of the [2k+2i+2i] annuladducts from different ketenes and imines.

Accelerating H2 Evolution by Anodic Semi-dehydrogenation of Tetrahydroisoquinolines in Water over Co3O4 Nanoribbon Arrays Decorated Nickel Foam

Coupling the H2 evolution reaction in water with thermodynamically favorable organic oxidation reactions is highly desirable, because it can enhance the energy conversion efficiency compared with electrocatalytic water splitting, and produce value-added chemicals instead of O2 in the anodic reaction. Herein, Co3O4 nanoribbon arrays in situ grown on nickel foam (Co3O4@NF) was employed as an effective electrocatalyst for the selective oxidation of tetrahydroisoquinolines (THIQs). Various value-added semi-dehydrogenation products including dihydroisoquinolines with electro-deficient or -rich groups could be obtained with moderate yields and faradaic efficiencies. Benefitting from the rich surface active sites of Co3O4@NF, a two-electrode (Co3O4@NF||Pt) electrolytic system drove a benchmark current density of 10 mA cm?2 at a cell voltage as low as 1.446 V in 1.0 M KOH aqueous solution containing 0.02 M THIQ, which was reduced by 174 mV in comparison with that of overall water splitting.

Synthesis and properties of a chiral bis-tetrahydroisoquinoline proton sponge

A new chiral proton sponge has been prepared, and the reasons for its unusually high basicity elucidated by a quantum chemical study.

A biomass-derived N-doped porous carbon catalyst for the aerobic dehydrogenation of nitrogen heterocycles

N-doped porous carbon (NC) was synthesized from sugar cane bagasse, which is a sustainable and widely available biomass waste. The preferred NC sample had a well-developed porous structure, a graphene-like surface morphology and different N species. More

Azolium Control of the Osmium-Promoted Aromatic C-H Bond Activation in 1,3-Disubstituted Substrates

The hexahydride complex OsH6(PiPr3)2 promotes the C-H bond activation of the 1,3-disubstituted phenyl group of the [BF4]- and [BPh4]- salts of the cations 1-(3-(isoquinolin-1-yl)phenyl)-3-methylimidazolium and 1-(3-(isoquinolin-1-yl)phenyl)-3-methylbenzimidazolium. The reactions selectively afford neutral and cationic trihydride-osmium(IV) derivatives bearing κ2-C,N- or κ2-C,C-chelating ligands, a cationic dihydride-osmium(IV) complex stabilized by a κ3-C,C,N-pincer group, and a bimetallic hexahydride formed by two trihydride-osmium(IV) fragments. The metal centers of the hexahydride are separated by a bridging ligand, composed of κ2-C,N- and κ2-C,C-chelating moieties, which allows electronic communication between the metal centers. The wide variety of obtained compounds and the high selectivity observed in their formation is a consequence of the main role of the azolium group during the activation and of the existence of significant differences in behavior between the azolium groups. The azolium role is governed by the anion of the salt, whereas the azolium behavior depends upon its imidazolium or benzimidazolium nature. While [BF4]- inhibits the azolium reactions, [BPh4]- favors the azolium participation in the activation process. In contrast to benzimidazolylidene, the imidazolylidene resulting from the deprotonation of the imidazolium substituent coordinates in an abnormal fashion to direct the phenyl C-H bond activation to the 2-position. The hydride ligands of the cationic dihydride-osmium(IV) pincer complex display intense quantum mechanical exchange coupling. Furthermore, this salt is a red phosphorescent emitter upon photoexcitation and displays a noticeable catalytic activity for the dehydrogenation of 1-phenylethanol to acetophenone and of 1,2-phenylenedimethanol to 1-isobenzofuranone. The bimetallic hexahydride shows catalytic synergism between the metals, in the dehydrogenation of 1,2,3,4-tetrahydroisoquinoline and alcohols.

Peganumine A alkaloid structure simplifier and application thereof

The invention discloses a Peganumine A alkaloid structure simplifier, a stereoisomer or a pharmaceutical salt thereof. The structure is shown in the following general formula: each substituent group is defined in the specification. The simplified structure of the Peganumine A alkaloid provided by the invention has a relatively obvious proliferation inhibition effect on liver cancer HepG2, lung cancer A549 and intestinal cancer HCT116, and the anti-tumor activity of part of compounds is higher than the anti-liver cancer HepG2 activity of Peganumine A reported in literatures.