3418-45-9

Usage

Uses

Used in Pharmaceutical Industry:
3-Quinolinol,1,2,3,4-tetrahydrois used as a key intermediate in the synthesis of various pharmaceuticals for its ability to form complex molecular structures that can target specific biological pathways.
Used in Agrochemical Industry:
3-Quinolinol,1,2,3,4-tetrahydrois used as a building block in the development of agrochemicals, contributing to the creation of effective compounds for pest and disease control in agriculture.
Used in Antimicrobial and Antifungal Applications:
3-Quinolinol,1,2,3,4-tetrahydrois used as an antimicrobial and antifungal agent, leveraging its potential to inhibit the growth of harmful microorganisms, thereby offering a means to control infections and maintain hygiene.
Used in Neurodegenerative Disease Treatment:
3-Quinolinol,1,2,3,4-tetrahydrois used in the research and development of treatments for neurodegenerative diseases, due to its potential to interact with neurological pathways and offer therapeutic benefits.
Used in Metal Extraction and Purification:
3-Quinolinol,1,2,3,4-tetrahydrois used as a chelating agent in the extraction and purification of metals, facilitating the separation and concentration of metal ions in various industrial processes.
Used in Metalworking Fluids:
3-Quinolinol,1,2,3,4-tetrahydrois used as a corrosion inhibitor in metalworking fluids, helping to prevent the deterioration of metal surfaces during manufacturing and machining processes.
Environmental Considerations:
3-Quinolinol,1,2,3,4-tetrahydrois considered a potential environmental hazard and has been subject to environmental risk assessments due to its potential toxicity to aquatic organisms, necessitating careful handling and disposal to minimize ecological impact.

InChI:InChI=1/C9H11NO/c11-8-5-7-3-1-2-4-9(7)10-6-8/h1-4,8,10-11H,5-6H2

Synthetic route

quinoline (91-22-5) → 1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) + 1,2,3,4-tetrahydroquinolin-2-ol

Conditions	Yield
Stage #1: quinoline With borane-THF; boron trichloride In hexane at 0 - 65℃; for 4h; Inert atmosphere; Stage #2: With sodium perborate; water at 20℃; for 2h; Reagent/catalyst; Inert atmosphere;	A 70% B 21%

3-hydroxyquinoline (580-18-7) → 1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9)

Conditions	Yield
With ethanol; sodium at 80℃; for 2h;	48%
With ethanol; palladium at 55℃; Hydrogenation;
With potassium hydroxide; water elektrochemische Reduktion;
With sulfuric acid; water elektrochemische Reduktion;
With ethanol; sodium

quinoline (91-22-5) → 1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9)

Conditions	Yield
Stage #1: quinoline With monochloroborane dimethyl sulfide complex In tetrahydrofuran at 0 - 65℃; for 48h; Inert atmosphere; Stage #2: With sodium perborate; water at 20℃; for 2h; Reagent/catalyst; Inert atmosphere;	45%
Multi-step reaction with 2 steps 1: tris(pentafluorophenyl)borate / chloroform-d1 / 24 h / 25 °C / Inert atmosphere 2: sodium perborate tetrahydrate / water; tetrahydrofuran / 1 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: tris(pentafluorophenyl)borate / chloroform-d1 / 24 h / 85 °C / Inert atmosphere 2: sodium perborate tetrahydrate / water; tetrahydrofuran / 1 h / 20 °C / Inert atmosphere View Scheme

3-hydroxyquinoline (580-18-7) + sulfuric acid (7664-93-9) + water (7732-18-5) → 1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9)

Conditions	Yield
bei der elektrochemischen Reduktion an Blei-Kathoden;

3-hydroxyquinoline (580-18-7) + water (7732-18-5) + KOH-solution → 1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9)

Conditions	Yield
bei der elektrochemischen Reduktion an Nickel-Kathoden;

C21H17B2NO4 → 1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9)

Conditions	Yield
With sodium perborate tetrahydrate In tetrahydrofuran; water at 20℃; for 1h; Inert atmosphere;

1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) + tert-butyldimethylsilyl chloride (18162-48-6) → 3-((tert-butyldimethylsilyl)oxy)-1,2,3,4-tetrahydroquinoline

Conditions	Yield
With 1H-imidazole In tetrahydrofuran at 80℃; for 12h;	38%

1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) + 1-bromomethyl-3-trifluoromethylbenzene (402-23-3) → 1-[[3-(trifluoromethyl)phenyl]methyl]-3,4-dihydro-2H-quinolin-3-ol

Conditions	Yield
With triethylamine In tetrahydrofuran at 25℃; for 12h;	18.4%

1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) → 1-(3-(3-((tert-butyldimethylsilyl)oxy)-3,4-dihydroquinolin-1(2H)-yl)-1-((S)-tetrahydrofuran-3-yl)-6,7-dihydro-1H-pyrazolo[4,3-c]pyridin-5(4H)-yl)ethanone

Conditions	Yield
Multi-step reaction with 2 steps 1: 1H-imidazole / tetrahydrofuran / 12 h / 80 °C 2: ruphos; dichloro[1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) / 1,4-dioxane / 16 h / 120 °C / Inert atmosphere View Scheme

1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) → 1-(3-(6-bromo-3-((tert-butyldimethylsilyl)oxy)-3,4-dihydroquinolin-1(2H)-yl)-1-((S)-tetrahydrofuran-3-yl)-6,7-dihydro-1H-pyrazolo[4,3-c]pyridin-5(4H)-yl)ethanone

Conditions	Yield
Multi-step reaction with 3 steps 1: 1H-imidazole / tetrahydrofuran / 12 h / 80 °C 2: ruphos; dichloro[1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) / 1,4-dioxane / 16 h / 120 °C / Inert atmosphere 3: N-Bromosuccinimide / dichloromethane / 2 h / 20 °C View Scheme

1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) → 1-(3-(3-((tert-butyldimethylsilyl)oxy)-6-(1-methyl-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)-1-((S)-tetrahydrofuran-3-yl)-6,7-dihydro-1H-pyrazolo[4,3-c]pyridin-5(4H)-yl)ethanone

Conditions

Yield

Multi-step reaction with 4 steps 1: 1H-imidazole / tetrahydrofuran / 12 h / 80 °C 2: ruphos; dichloro[1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) / 1,4-dioxane / 16 h / 120 °C / Inert atmosphere 3: N-Bromosuccinimide / dichloromethane / 2 h / 20 °C 4: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 12 h / 110 °C / Inert atmosphere View Scheme

1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) → (S)-1-[3-[3-hydroxy-6-(1-methylpyrazol-4-yl)-3,4-dihydro-2H-quinolin-1-yl]-1-tetrahydrofuran-3-yl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridin-5-yl]ethanone

Conditions

Yield

Multi-step reaction with 5 steps 1: 1H-imidazole / tetrahydrofuran / 12 h / 80 °C 2: ruphos; dichloro[1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) / 1,4-dioxane / 16 h / 120 °C / Inert atmosphere 3: N-Bromosuccinimide / dichloromethane / 2 h / 20 °C 4: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 12 h / 110 °C / Inert atmosphere 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 80 °C / Inert atmosphere View Scheme

1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) → (S)-1-[3-[3-methoxy-6-(1-methylpyrazol-4-yl)-3,4-dihydro-2H-quinolin-1-yl]-1-tetrahydrofuran-3-yl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridin-5-yl]ethanone

Conditions

Yield

Multi-step reaction with 6 steps 1.1: 1H-imidazole / tetrahydrofuran / 12 h / 80 °C 2.1: ruphos; dichloro[1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) / 1,4-dioxane / 16 h / 120 °C / Inert atmosphere 3.1: N-Bromosuccinimide / dichloromethane / 2 h / 20 °C 4.1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 12 h / 110 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 80 °C / Inert atmosphere 6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 6.2: 16 h / 0 - 25 °C View Scheme

1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) → 1-(5-acetyl-1-((S)-tetrahydrofuran-3-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl)-6-(1-methyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydroquinolin-3-yl methanesulfonate

Conditions

Yield

Multi-step reaction with 6 steps 1: 1H-imidazole / tetrahydrofuran / 12 h / 80 °C 2: ruphos; dichloro[1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) / 1,4-dioxane / 16 h / 120 °C / Inert atmosphere 3: N-Bromosuccinimide / dichloromethane / 2 h / 20 °C 4: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 12 h / 110 °C / Inert atmosphere 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 80 °C / Inert atmosphere 6: triethylamine / dichloromethane / 2 h / 0 - 25 °C View Scheme

1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) → (S)-1-(5-acetyl-1-tetrahydrofuran-3-yl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridin-3-yl)-6-(1-methylpyrazol-4-yl)-3,4-dihydro-2H-quinoline-3-carbonitrile + (S)-2-[1-(5-acetyl-1-tetrahydrofuran-3-yl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridin-3-yl)-5-(1-methylpyrazol-4-yl)indolin-2-yl]acetonitrile

Conditions

Yield

Multi-step reaction with 7 steps 1: 1H-imidazole / tetrahydrofuran / 12 h / 80 °C 2: ruphos; dichloro[1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) / 1,4-dioxane / 16 h / 120 °C / Inert atmosphere 3: N-Bromosuccinimide / dichloromethane / 2 h / 20 °C 4: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 12 h / 110 °C / Inert atmosphere 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 80 °C / Inert atmosphere 6: triethylamine / dichloromethane / 2 h / 0 - 25 °C 7: dimethyl sulfoxide / 16 h / 20 °C View Scheme

1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) → 6-bromo-1,2,3,4-tetrahydroquinolin-3-ol

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 15h;

1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) → 6-bromo-3-((tert-butyldimethylsilyl)oxy)-1,2,3,4-tetrahydroquinoline

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C 2: dichloromethane / 0.83 h / 0 - 20 °C View Scheme

1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) → (6-bromo-3-((tert-butyldimethylsilyl)oxy)-3,4-dihydroquinolin-1(2H)-yl)(3-chlorophenyl)methanone

Conditions	Yield
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C 2: dichloromethane / 0.83 h / 0 - 20 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 20 °C View Scheme

1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) → (6-bromo-3-hydroxy-3,4-dihydroquinolin-1(2H)-yl)(3-chlorophenyl)methanone

Conditions	Yield
Multi-step reaction with 4 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C 2: dichloromethane / 0.83 h / 0 - 20 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 20 °C 4: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 0 °C View Scheme

1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) → (6-bromo-3-fluoro-3,4-dihydroquinolin-1(2H)-yl)(3-chlorophenyl)methanone

Conditions	Yield
Multi-step reaction with 5 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C 2: dichloromethane / 0.83 h / 0 - 20 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 20 °C 4: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 0 °C 5: diethylamino-sulfur trifluoride / dichloromethane / 1.5 h / 0 °C View Scheme

1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) → tert-butyl 2-(1-(3-chlorobenzoyl)-3-fluoro-1,2,3,4-tetrahydroquinolin-6-yl)acetate

Conditions

Yield

Multi-step reaction with 6 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C 2: dichloromethane / 0.83 h / 0 - 20 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 20 °C 4: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 0 °C 5: diethylamino-sulfur trifluoride / dichloromethane / 1.5 h / 0 °C 6: tris-(dibenzylideneacetone)dipalladium(0); XPhos / tetrahydrofuran / 7 h / 65 °C / Microwave irradiation; Inert atmosphere View Scheme

1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) → tert-butyl 2-(1-(3-chlorobenzoyl)-3-fluoro-1,2,3,4-tetrahydroquinolin-6-yl)propanoate

Conditions

Yield

Multi-step reaction with 7 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C 2.1: dichloromethane / 0.83 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 20 °C 4.1: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 0 °C 5.1: diethylamino-sulfur trifluoride / dichloromethane / 1.5 h / 0 °C 6.1: tris-(dibenzylideneacetone)dipalladium(0); XPhos / tetrahydrofuran / 7 h / 65 °C / Microwave irradiation; Inert atmosphere 7.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / -78 °C 7.2: 1.75 h / -78 - 20 °C View Scheme

1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) → 2-(1-(3-chlorobenzoyl)-3-fluoro-1,2,3,4-tetrahydroquinolin-6-yl)propanoic acid

Conditions

Yield

Multi-step reaction with 8 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C 2.1: dichloromethane / 0.83 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 20 °C 4.1: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 0 °C 5.1: diethylamino-sulfur trifluoride / dichloromethane / 1.5 h / 0 °C 6.1: tris-(dibenzylideneacetone)dipalladium(0); XPhos / tetrahydrofuran / 7 h / 65 °C / Microwave irradiation; Inert atmosphere 7.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / -78 °C 7.2: 1.75 h / -78 - 20 °C 8.1: hydrogenchloride / dichloromethane / 5 h / 0 - 20 °C View Scheme

1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) → 6-bromo-1-(2-methylpyrimidin-4-yl)-1,2,3,4-tetrahydroquinolin-3-ol

Conditions	Yield
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C 2: dichloromethane / 0.83 h / 0 - 20 °C 3: toluene-4-sulfonic acid / 1,4-dioxane / 1 h / 160 °C / Microwave irradiation View Scheme

1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) → 6-bromo-3-fluoro-1-(2-methylpyrimidin-4-yl)-1,2,3,4-tetrahydroquinoline

Conditions	Yield
Multi-step reaction with 4 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C 2: dichloromethane / 0.83 h / 0 - 20 °C 3: toluene-4-sulfonic acid / 1,4-dioxane / 1 h / 160 °C / Microwave irradiation 4: diethylamino-sulfur trifluoride / dichloromethane / 3 h / 0 °C View Scheme

1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) → 3-fluoro-1-(2-methylpyrimidin-4-yl)-1,2,3,4-tetrahydroquinoline-6-carbonitrile

Conditions

Yield

Multi-step reaction with 5 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C 2: dichloromethane / 0.83 h / 0 - 20 °C 3: toluene-4-sulfonic acid / 1,4-dioxane / 1 h / 160 °C / Microwave irradiation 4: diethylamino-sulfur trifluoride / dichloromethane / 3 h / 0 °C 5: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 0.67 h / 140 °C / Inert atmosphere; Microwave irradiation View Scheme

1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) → 1-(3-fluoro-1-(2-methylpyrimidin-4-yl)-1,2,3,4-tetrahydroquinolin-6-yl)cyclopropanamine

Conditions

Yield

Multi-step reaction with 6 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C 2: dichloromethane / 0.83 h / 0 - 20 °C 3: toluene-4-sulfonic acid / 1,4-dioxane / 1 h / 160 °C / Microwave irradiation 4: diethylamino-sulfur trifluoride / dichloromethane / 3 h / 0 °C 5: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 0.67 h / 140 °C / Inert atmosphere; Microwave irradiation 6: titanium(IV) isopropylate / tetrahydrofuran / 5.67 h / 20 °C View Scheme

1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) → 4-chloro-N-(1-(3-fluoro-1-(2-methylpyrimidin-4-yl)-1,2,3,4-tetrahydroquinolin-6-yl)cyclopropyl)benzamide 2,2,2-trifluoroacetate salt

Conditions

Yield

Multi-step reaction with 7 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C 2: dichloromethane / 0.83 h / 0 - 20 °C 3: toluene-4-sulfonic acid / 1,4-dioxane / 1 h / 160 °C / Microwave irradiation 4: diethylamino-sulfur trifluoride / dichloromethane / 3 h / 0 °C 5: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 0.67 h / 140 °C / Inert atmosphere; Microwave irradiation 6: titanium(IV) isopropylate / tetrahydrofuran / 5.67 h / 20 °C 7: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C View Scheme

1,2,3,4-tetrahydroquinolin-3-ol (3418-45-9) → 2-(1-(3-chlorobenzoyl)-3-fluoro-1,2,3,4-tetrahydroquinolin-6-yl)-N-(4-chlorophenyl)propanamide

Conditions

Yield

Multi-step reaction with 9 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 0 - 20 °C 2.1: dichloromethane / 0.83 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 20 °C 4.1: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 0 °C 5.1: diethylamino-sulfur trifluoride / dichloromethane / 1.5 h / 0 °C 6.1: tris-(dibenzylideneacetone)dipalladium(0); XPhos / tetrahydrofuran / 7 h / 65 °C / Microwave irradiation; Inert atmosphere 7.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / -78 °C 7.2: 1.75 h / -78 - 20 °C 8.1: hydrogenchloride / dichloromethane / 5 h / 0 - 20 °C 9.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1.5 h / 0 - 20 °C View Scheme

Upstream product

• 580-18-7 3-hydroxyquinoline 
• 7664-93-9 sulfuric acid 
• 7732-18-5 water 
• 91-22-5 quinoline 

Relevant academic research and scientific papers

Double Hydroboration of Quinolines via Borane Catalysis: Diastereoselective One Pot Synthesis of 3-Hydroxytetrahydroquinolines

Described herein is an organoborane-catalysed consecutive borylative reduction of quinolines and isoquinolines to furnish tetrahydro(iso)quinolines bearing a C(sp3)?B bond β to the nitrogen atom. The installed C?B bond is oxidatively transformed to the hydroxy group in one pot. The present double hydroboration is proposed to proceed via a stepwise ionic mechanism involving a boronium ion. The stereo-outcome was found to be dependent on the position (C2 vs C4) of the substituents in quinolines. (Figure presented.).

β-Hydroxy-tetrahydroquinolines from Quinolines Using Chloroborane: Synthesis of the Peptidomimetic FISLE-412

A new synthetic protocol provides a simple and direct method to generate functionalized β-hydroxy-tetrahydroquinolines (THQs). Hydroboration of quinolines using chloroboranes followed by oxidation with NaBO3?H2O led to the formation of functionalized β-hydroxy THQs. High regio- and diastereoselectivities were observed in α and γ substituted quinolines and the trans diastereomer of the β-hydroxy-THQ was the major isostere. This new protocol was utilized to build the novel antibody-targeted lupus peptidomimetic, FISLE-412.

4,5,6,7-TETRAHYDRO-1 H-PYRAZOLO[4,3-C]PYRIDIN-3-AMINE COMPOUNDS AS CBP AND/OR EP300 INHIBITORS

The present invention relates to compounds of formula (I) or formula (II): and to salts thereof, wherein R1-R4 of formula (I) and R1-R3 of formula (II) have any of the values defined herein, and compositions and uses thereof. The compounds are useful as inhibitors of CBP and/or EP300. Also included are pharmaceutical compositions comprising a compound of formula (I) of formula (II) or a pharmaceutically acceptable salt thereof, and methods of using such compounds and salts in the treatment of various CBP and/or EP300-mediated disorders.