5840-01-7

Basic information

• Product Name: Lilolidine
• Synonyms: (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-17-[2-(4-methylpiperazin-1-yl)acetyl]-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one;(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-17-[2-(4-methylpiperazin-1-yl)ethanoyl]-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one;Lilolidene;Lilolidine AutonaMe: 2,3-dihydro-1H-pyrrolo[3,2,1-ij]quinoline;2,3-dihydro-1H-pyrrolo[3,2,1-ij]quinoline, 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline;5,6-Dihydro-4H-pyrrolo[3,2,1-IJ]quinoline, 97%, 97%;Lilolidine;2,3-dihydro-1H-pyrrolo[3,2,1-ij]quinoline
• CAS NO: 5840-01-7
• Molecular Formula: C₁₁H₁₁N
• Molecular Weight: 157.21174
• EINECS: 1312995-182-4
• Product Categories: Pale White Powder
• Mol File: 5840-01-7.mol

Chemical Properties

• Melting Point: 80-81°C
• Boiling Point: 318.377 °C at 760 mmHg
• Flash Point: 146.349 °C
• Appearance: /
• Density: 1.16
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.656
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: Lilolidine(CAS DataBase Reference)
• NIST Chemistry Reference: Lilolidine(5840-01-7)
• EPA Substance Registry System: Lilolidine(5840-01-7)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 5840-01-7(Hazardous Substances Data)

Usage

Uses

Acts as a reagent primarily in reactions of ring-expansions with indoles.

InChI:InChI=1/C11H11N/c1-3-9-5-2-7-12-8-6-10(4-1)11(9)12/h1,3-4,6,8H,2,5,7H2

Synthetic route

5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid (124730-56-9) → 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7)

Conditions	Yield
With quinoline; copper chromite at 185℃; for 3h;	93%
With quinoline; copper chromite at 185℃; for 2h;	72%
With copper chromite In quinoline at 185℃; for 2h;	72%
With quinoline; copper chromite at 185℃; for 4h;	58%
copper(II) chromite In quinoline at 185℃; for 4h;	58%

5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-one (16078-37-8) → 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7)

Conditions	Yield
Stage #1: 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-one With diisobutylaluminium hydride In tetrahydrofuran; toluene at -20 - -10℃; Stage #2: With hydrogenchloride In tetrahydrofuran; water; toluene at 40℃; for 0.5h; Temperature; Concentration; Reagent/catalyst;	88.9%

5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline 1,2-dicarboxylic acid (1220339-77-4) → 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7)

Conditions	Yield
Stage #1: 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline 1,2-dicarboxylic acid With quinoline; copper at 238℃; for 3h; Stage #2: With hydrogenchloride In water Stage #3: With sodium hydroxide In water	72%

1,2,3,4-tetrahydroisoquinoline (635-46-1) + ethylene glycol (107-21-1) → 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7)

Conditions	Yield
With Pt/Al2O3; zinc(II) oxide In neat (no solvent) at 175℃; for 24h; Sealed tube;	50%

1,2,3,4-tetrahydroisoquinoline (635-46-1) + ethylene glycol (107-21-1) → 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) + 2-[1,2,3,4-tetrahydroquinolin-1-yl]ethan-1-ol (52704-48-0)

Conditions	Yield
With palladium on activated charcoal; zinc(II) oxide In water at 150℃; for 24h; Sealed tube;	A 45% B 45%
With palladium on activated charcoal; zinc(II) oxide In water at 150℃; for 24h; Sealed tube;

quinoline (91-22-5) + ethylene glycol (107-21-1) → 1,2,3,4-tetrahydroisoquinoline (635-46-1) + 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7)

Conditions	Yield
With palladium 10% on activated carbon; zinc In water at 150℃; for 24h; Autoclave;	A 37% B 16%
With palladium 10% on activated carbon; zinc In water at 150℃; for 40h; Autoclave;	A 33 %Spectr. B 33 %Spectr.
With palladium 10% on activated carbon; zinc In water at 150℃; for 70h; Autoclave;	A 45 %Spectr. B 50 %Spectr.

5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid (117273-45-7) → 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7)

Conditions	Yield
With quinoline; copper oxide-chromium oxide; hydrogen at 190℃;

[(E)-8-Allyl-3,4-dihydro-2H-quinolin-1-ylimino]-acetic acid (1026530-18-6) → 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7)

Conditions	Yield
With potassium hydroxide; sulfuric acid 1.) ethanol, 120 deg C, 4 h, 2.) ethanol, reflux, 4 h; Yield given. Multistep reaction;

2-[(E)-8-Allyl-3,4-dihydro-2H-quinolin-1-ylimino]-propionic acid ethyl ester → 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7)

Conditions	Yield
With pyridine; sulfuric acid; acetic anhydride 1.) ethanol, 3.5 h; Yield given. Multistep reaction;

1-allyl-7-bromo-1H-indole (194231-71-5) → 1-allylindole (16886-08-1) + 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene for 12h; Heating; Yield given. Yields of byproduct given;
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene for 12h; Product distribution; Heating; different N-substituted-7-bromoindoles;

1,2,3,4-tetrahydroisoquinoline (635-46-1) → 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: tetrahydrofuran / 24 h / Ambient temperature 2: MgCl2 / 2-methoxy-ethanol; tetrahydrofuran / 6 h / 125 °C 3: 94 percent / aq. NaOH / ethanol / 2 h / Heating 4: 93 percent / copper chromite, quinoline / 3 h / 185 °C View Scheme
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon / 24 h / 150 °C / Autoclave 2: palladium 10% on activated carbon; zinc / water / 24 h / 150 °C / Autoclave View Scheme
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon / 24 h / 150 °C / Autoclave 2: palladium 10% on activated carbon; zinc / water / 70 h / 150 °C / Autoclave View Scheme

5,6-dihydro-4H-pyrrolo [3,2,1-ij]quinoline-1-carboxylic acid ethyl ester (124730-53-6) → 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / aq. NaOH / ethanol / 2 h / Heating 2: 93 percent / copper chromite, quinoline / 3 h / 185 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide; water / ethanol / 2 h / Reflux 2: copper chromite / quinoline / 2 h / 185 °C View Scheme

3-(3,4-dihydro-2H-quinolin-1-yl)-2-oxopropionic acid ethyl ester (152712-44-2) → 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: MgCl2 / 2-methoxy-ethanol; tetrahydrofuran / 6 h / 125 °C 2: 94 percent / aq. NaOH / ethanol / 2 h / Heating 3: 93 percent / copper chromite, quinoline / 3 h / 185 °C View Scheme
Multi-step reaction with 3 steps 1: magnesium chloride / 2-methoxy-ethanol / 6 h / 125 °C / Reflux 2: sodium hydroxide; water / ethanol / 2 h / Reflux 3: copper chromite / quinoline / 2 h / 185 °C View Scheme

8-allyl-1,2,3,4-tetrahydroquinoline hydrochloride (92679-18-0) → 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 94.8 percent / CF3COOH / acetonitrile / 4 h 2: 88.6 percent / 1.8 N aq. sodium hypochlorite, 2.6 N aq. NaOH / ethanol / 1 h / 70 °C 3: 93 percent / 66percent aq. AcOH / 1 h / Ambient temperature 4: 1.) 10percent aq. H2SO4, 2.) Ac2O, pyridine / 1.) ethanol, 3.5 h View Scheme
Multi-step reaction with 4 steps 1: 94.8 percent / CF3COOH / acetonitrile / 4 h 2: 88.6 percent / 1.8 N aq. sodium hypochlorite, 2.6 N aq. NaOH / ethanol / 1 h / 70 °C 3: 0.2percent aq. H2SO4 / ethanol / 2 h / Ambient temperature 4: 1.) aq. H2SO4, 2.) 30percent aq. KOH / 1.) ethanol, 120 deg C, 4 h, 2.) ethanol, reflux, 4 h View Scheme

8-allyl-1-carbamoyl-1,2,3,4-tetrahydroquinoline (152771-24-9) → 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 88.6 percent / 1.8 N aq. sodium hypochlorite, 2.6 N aq. NaOH / ethanol / 1 h / 70 °C 2: 93 percent / 66percent aq. AcOH / 1 h / Ambient temperature 3: 1.) 10percent aq. H2SO4, 2.) Ac2O, pyridine / 1.) ethanol, 3.5 h View Scheme
Multi-step reaction with 3 steps 1: 88.6 percent / 1.8 N aq. sodium hypochlorite, 2.6 N aq. NaOH / ethanol / 1 h / 70 °C 2: 0.2percent aq. H2SO4 / ethanol / 2 h / Ambient temperature 3: 1.) aq. H2SO4, 2.) 30percent aq. KOH / 1.) ethanol, 120 deg C, 4 h, 2.) ethanol, reflux, 4 h View Scheme

8-allyl-1-amino-1,2,3,4-tetrahydroquinoline (152771-25-0) → 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / 66percent aq. AcOH / 1 h / Ambient temperature 2: 1.) 10percent aq. H2SO4, 2.) Ac2O, pyridine / 1.) ethanol, 3.5 h View Scheme
Multi-step reaction with 2 steps 1: 0.2percent aq. H2SO4 / ethanol / 2 h / Ambient temperature 2: 1.) aq. H2SO4, 2.) 30percent aq. KOH / 1.) ethanol, 120 deg C, 4 h, 2.) ethanol, reflux, 4 h View Scheme

quinoline (91-22-5) + ethylene glycol (107-21-1) → 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7)

Conditions	Yield
With palladium 10% on activated carbon; zinc In water at 150℃; for 24h; Autoclave;	30 %Spectr.

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → C17H22BNO2

Conditions	Yield
With benzylidene dichloride; C14H14N3P; N-ethyl-N,N-diisopropylamine In acetonitrile for 16h; regioselective reaction;	98%

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) + 2-((trifluoromethyl)thio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide → 1-((trifluoromethyl)thio)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

Conditions	Yield
In 2,2,2-trifluoroethanol at 40℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube;	97%

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) → C11H10(2)HN

Conditions	Yield
With water-d2; silver trifluoromethanesulfonate In chloroform-d1 at 90℃; for 18h; regioselective reaction;	96%

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) + 2-((trifluoromethyl)sulfonyl)benzo[d]thiazole → 1-((trifluoromethyl)sulfinyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

Conditions	Yield
With Diphenylphosphinic chloride In acetonitrile at 60℃; for 1h; Schlenk technique; Inert atmosphere;	95%

methanol (67-56-1) + 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) + oxalyl dichloride (79-37-8) + sodium methylate (124-41-4) → (5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)oxoacetic acid methyl ester (345264-02-0)

Conditions	Yield
Stage #1: 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline; oxalyl dichloride In tetrahydrofuran at 0℃; for 2.5h; Stage #2: methanol; sodium methylate In tetrahydrofuran at -78℃;	94%
Stage #1: 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline; oxalyl dichloride In tetrahydrofuran; dichloromethane at 0℃; for 0.5h; Stage #2: methanol; sodium methylate In tetrahydrofuran; dichloromethane at -78 - 20℃; for 2h;	87%

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) → 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione (4290-72-6)

Conditions	Yield
With oxygen; Rose Bengal lactone In water; N,N-dimethyl-formamide for 48h; Inert atmosphere; Irradiation;	93%

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) + 1,1,1,3',3',3'-hexafluoro-propanol (920-66-1) → 2-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol

Conditions	Yield
With copper diacetate; 4,4'-di-tert-butyl-2,2'-bipyridine at 90℃; for 24h; Schlenk technique; regioselective reaction;	92%

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) + 2-vinylbenzaldehyde (28272-96-0) → 8-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-13-methyl-5,6-dihydro-4H-benzo[b]pyrido[3,2,1-jk]carbazole

Conditions	Yield
With dipotassium peroxodisulfate; tetrakis(acetonitrile)palladium bistriflate In acetonitrile at 60℃; for 18h; Inert atmosphere; Schlenk technique; Sealed tube; regioselective reaction;	91%

2,6-Dichloropyrimidine (3934-20-1) + 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) → 1-(2-chloropyrimidin-4-yl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

Conditions	Yield
Stage #1: 2,6-Dichloropyrimidine With aluminum (III) chloride In 1,2-dimethoxyethane at 20℃; for 0.333333h; Stage #2: 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline In 1,2-dimethoxyethane at 80℃; for 6h;	90.1%
With iron(III) chloride In 1,2-dichloro-ethane at 60℃;
Stage #1: 2,6-Dichloropyrimidine With aluminum (III) chloride In 1,2-dimethoxyethane at 20℃; for 0.333333h; Stage #2: 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline In 1,2-dimethoxyethane at 80℃; for 6h;
Stage #1: 2,6-Dichloropyrimidine With aluminum (III) chloride In 1,2-dimethoxyethane at 20℃; for 0.333333h; Stage #2: 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline In 1,2-dimethoxyethane at 80℃; for 6h;

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) + Thiram (137-26-8) → 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl N,N-dimethylaminodithioformate

Conditions	Yield
With dipotassium peroxodisulfate; potassium iodide at 60℃; for 12h;	89%
With dipotassium peroxodisulfate; potassium iodide In water; N,N-dimethyl-formamide at 60℃; for 12h; Green chemistry;	89%

4-Methoxystyrene (637-69-4) + 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) + 1,3-dioxoisoindolin-2-yl (3r,5r,7r)-adamantane-1- carboxylate (118334-83-1) → 1-(2-(-adamantan-1-yl)-1-(4-methoxyphenyl)ethyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

Conditions	Yield
With indium(III) triflate; tris[2-phenylpyridinato-C2,N]iridium(III) at 30℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation;	88%

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) + 1,1,1-trifluoro-2-phenylbut-3-yn-2-yl 2,3,4,5,6-pentafluorobenzoate → C21H16F3N

Conditions	Yield
With 4-methyl-morpholine; copper(I) triflate benzene complex; 2,6-bis[(4S,5R)-4,5-diphenyl-4,5-dihydro-1,3-oxazol-2-yl]pyridine In methanol at 0℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction;	86%

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) + sodium methylate (124-41-4) → (5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)oxoacetic acid methyl ester (345264-02-0)

Conditions	Yield
Stage #1: 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline; oxalyl dichloride In diethyl ether at 0℃; for 0.5 - 0.75h; Stage #2: sodium methylate In methanol; diethyl ether at -78 - 20℃;	85%

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) + oxalyl dichloride (79-37-8) + sodium methylate (124-41-4) → (5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)oxoacetic acid methyl ester (345264-02-0)

Conditions	Yield
Stage #1: 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline; oxalyl dichloride In diethyl ether at 0℃; Stage #2: sodium methylate In methanol at -78 - 20℃;	85%
Stage #1: 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline; oxalyl dichloride In diethyl ether at 0℃; for 0.666667h; Stage #2: sodium methylate In methanol; diethyl ether at -78 - 24℃; for 2h;	84%

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) + sodium trifluoroethylsulfinate → 1-((2,2,2-trifluoroethyl)thio)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]-quinoline

Conditions	Yield
With chloro-trimethyl-silane; phosphonic acid diethyl ester In acetonitrile at 85℃; for 3h; Sealed tube;	85%

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) + ethyl 2-diazo-3-oxobutanoate (2009-97-4) → ethyl 2,2-bis(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-3-oxobutanoate

Conditions	Yield
With air In 2,2,2-trifluoroethanol; water at 120℃; for 12h; Sealed tube;	85%

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) + diethyl (bromodifluoromethyl)phosphonate (65094-22-6) → 1-((difluoromethyl)thio)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

Conditions	Yield
Stage #1: 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline With water; iodine; thiourea; potassium iodide In 1,4-dioxane at 50℃; Stage #2: With sodium hydroxide In 1,4-dioxane at 50℃; for 1h; Stage #3: diethyl (bromodifluoromethyl)phosphonate In 1,4-dioxane at 20℃; for 4h;	80%

1,2,4-Triazole (288-88-0) + 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) → C13H12N4

Conditions	Yield
With 5-ethyl-1,3,7,8-tetramethylalloxazinium triflate; iodine; oxygen In acetonitrile at 50℃; under 760.051 Torr; for 36h; Green chemistry;	79%

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) → C22H20N2

Conditions	Yield
With oxygen; palladium diacetate; acetic acid In dimethyl sulfoxide at 40℃; under 760.051 Torr; for 24h; regioselective reaction;	76%

4-Methoxystyrene (637-69-4) + 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) + acetonitrile (75-05-8) → 4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(4-methoxyphenyl)butanenitrile

Conditions	Yield
With indium(III) triflate; silver carbonate at 120℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;	75%

NH-pyrazole (288-13-1) + 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) → C14H13N3

Conditions	Yield
With 5-ethyl-1,3,7,8-tetramethylalloxazinium triflate; iodine; oxygen In acetonitrile at 50℃; under 760.051 Torr; for 36h; Green chemistry;	75%

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) + difluoromethylsulfinyl chloride → 1-((difluoromethyl)thio)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

Conditions	Yield
In acetonitrile at 90℃; for 6h; Inert atmosphere;	73%

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) + 2,2,2-trifluoroethanol (75-89-8) → 1-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-2,2,2-trifluoroethan-1-ol

Conditions	Yield
With copper diacetate; 4,4'-di-tert-butyl-2,2'-bipyridine at 90℃; for 24h; Schlenk technique; regioselective reaction;	73%

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) + C19H17NO4 → 1-((2R,4R,4aR,10aS)-4-(nitromethyl)-2-phenyl-3,4,4a,10a-tetrahydro-2H,5H-pyrano[2,3-b]chromen-2-yl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 0℃; Inert atmosphere; Molecular sieve; chemoselective reaction;	72%

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) + 2,2'-diiodobiphenyl (2236-52-4) → C23H17N

Conditions	Yield
With palladium(II) trimethylacetate; silver carbonate In dimethyl sulfoxide; N,N-dimethyl-formamide at 80℃; for 19h;	72%

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) + 4-chloro-6,7-bis(2-methoxyethoxy)quinazoline (183322-18-1) → 1-(6,7-bis(2-methoxyethoxy)quinazolin-4-yl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

Conditions	Yield
With 1,1,1,3',3',3'-hexafluoro-propanol; bis(trifluoromethanesulfonyl)amide at 100℃; for 6h; Sealed tube;	72%

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline (5840-01-7) + 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine (24415-66-5) → 1-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolinone

Conditions	Yield
With 1,1,1,3',3',3'-hexafluoro-propanol; bis(trifluoromethanesulfonyl)amide at 100℃; for 6h; Sealed tube;	72%
With 1,1,1,3',3',3'-hexafluoro-propanol; bis(trifluoromethanesulfonyl)amide at 100℃; for 6h; Microwave irradiation; Sealed tube;	72%

Upstream product

• 117273-45-7 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic acid 
• 1026530-18-6 [(E)-8-Allyl-3,4-dihydro-2H-quinolin-1-ylimino]-acetic acid 
• 124730-56-9 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid 
• 194231-71-5 1-allyl-7-bromo-1H-indole 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 124730-53-6 5,6-dihydro-4H-pyrrolo [3,2,1-ij]quinoline-1-carboxylic acid ethyl ester 
• 152712-44-2 3-(3,4-dihydro-2H-quinolin-1-yl)-2-oxopropionic acid ethyl ester 
• 92679-18-0 8-allyl-1,2,3,4-tetrahydroquinoline hydrochloride 
• 152771-24-9 8-allyl-1-carbamoyl-1,2,3,4-tetrahydroquinoline 
• 152771-25-0 8-allyl-1-amino-1,2,3,4-tetrahydroquinoline 
• 1220339-77-4 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline 1,2-dicarboxylic acid 
• 91-22-5 quinoline 
• 107-21-1 ethylene glycol 
• 16078-37-8 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-one 

Downstream Products

• 480-73-9 1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline 
• 345264-02-0 (5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)oxoacetic acid methyl ester 
• 345261-20-3 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dion 
• 905854-02-6 Tivantinib 
• 1000873-98-2 (±)-cis-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione 
• 1000873-98-2 (±)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione 
• 1313508-66-5 (3R,4R)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione pseudoephedrine complex 
• 1312995-22-4 N-((1-(4-chlorophenylsulfonyl)piperidin-4-yl)methyl)-4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)pyrimidin-2-amine trifluoroacetate 
• 1383937-41-4 3-[6-(benzyloxy)-1H-indol-3-yl]-4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-1H-pyrrole-2,5-dione 
• 905854-16-2 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(2-chloro-4-fluorophenyl)pyrrole-2,5-dione 
• 1000873-98-2 3(S),4(R)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione 
• 1000873-98-2 tivatinib 
• 905854-03-7 (+)-3(S),4(S)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-j]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione 
• 905854-06-0 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(3-methoxyphenyl)pyrrole-2,5-dione 

Relevant articles and documents

Straight Access to Indoles from Anilines and Ethylene Glycol by Heterogeneous Acceptorless Dehydrogenative Condensation

The development of original strategies for the preparation of indole derivatives is a major goal in drug design. Herein, we report the first straight access to indoles from anilines and ethylene glycol by heterogeneous catalysis, based on an acceptorless dehydrogenative condensation, under noninert conditions. In order to achieve high selectivity, a combination of Pt/Al2O3 and ZnO have been found to slowly dehydrogenate ethylene glycol generating, after condensation with the amine and tautomeric equilibrium, the corresponding pyrrole-ring unsubstituted indoles.

β-Amino alcohols from anilines and ethylene glycol through heterogeneous Borrowing Hydrogen reaction

Borrowing Hydrogen (BH), also called Hydrogen Autotransfer (HA), reaction with neat ethylene glycol represents a key step in the preparation of β-amino alcohols. However, due to the stability of ethylene glycol, mono-activation has rarely been achieved. Herein, a combination of Pd/C and ZnO is reported as heterogeneous catalyst for this BH/HA reaction. This system results in an extremely air and moisture stable, and economic catalyst able to mono-functionalize ethylene glycol in water, without further activation of the diol. In this work, different diols and aromatic amines have been explored affording a new approach towards amino alcohols. This study reveals how the combination of two solid species can afford interesting catalytic properties in heterogeneous phase. ZnO activates ethylene glycol while Pd/C is the responsible of the BH/HA cycle. This catalytic system has also been found useful to dehydrogenate indoles affording indolines that undergo in situ BH/HA cycle prior to re-aromatization, representing a tandem heterogeneous process.

Heterogeneous borrowing hydrogen reactions with Pd/C and ZnO: Diol scope

A borrowing hydrogen reaction with different diols was employed for the preparation of complex beta- gamma- or epsilon-amino alcohols from p-toluidine and tetrahydroquinoline with the aim of better understanding the applicability of the Pd/C ZnO heterogeneous catalyst.

METHOD FOR PRODUCING TRICYCLIC HETEROCYCLIC COMPOUND

It is an object of the present invention to provide a method for producing a high-purity tricyclic heterocyclic compound represented by formula (I), which is useful as a production intermediate for a pharmaceutical agent, wherein the method is an efficient production method with short steps and with a high yield, which does not use, as raw materials, expensive bromopyruvate and highly harmful copper chromite, and does not need silica gel column chromatography that generates, as by-products, large quantities of waste. The present invention relates to production of Compound (I) by the following method.

COMBINATIONAL COMPOSITIONS AND METHODS FOR TREATMENT OF CANCER

The present invention provides methods of treating a cell proliferative disorder, such as a cancer, by administering to a subject in need thereof a therapeutically effective amount of a pyrroloquinolinyl-pyrrole-2,5-dione compound or a pyrroloquinolinyl-pyrrolidine-2,5-dione compound in combination with a therapeutically effective amount of a second anti-proliferative agent.

An efficient one pot transfer hydrogenation and N-alkylation of quinolines with alcohols mediated by Pd/C/Zn

A Pd/C/Zn mixture with alcohols has been revealed to be an efficient transfer hydrogenation system to quinolines. Furthermore, the metals mixture is able to activate alcohols as N-alkylating agents in a hydrogen autotransfer process. 1,2,3,4-Tetrahydroquinolines and N-alkylated tetrahydroquinolines from quinolines have been obtained with excellent yields in one step.

MELEIMIDE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS AND METHODS FOR TREATMENT OF CANCER

The present invention relates to pyrroloquinolinyl-pyrrole-2,5-dione compounds and pyrroloquinolinyl-pyrrolidine-2,5-dione compounds, and methods of preparation of these compounds. The present invention also relates to pharmaceutical compositions comprising pyrroloquinolinyl-pyrrole-2,5-dione compounds and pyrroloquinolinyl-pyrrolidine-2,5-dione compounds. The present invention provides methods of treating a cell proliferative disorder, such as a cancer, by administering to a subject in need thereof a therapeutically effective amount of a pyrroloquinolinyl-pyrrole-2,5-dione compound or pyrroloquinolinyl-pyrrolidine-2,5-dione compound of the present invention.

PURINE DERIVATIVES AS KINASE INHIBITORS

The present invention provides kinase inhibitors of Formula I.