244-76-8

Usage

Chemical Properties

Light Brown Solid

Uses

A carcinogenic compound formed during cooking processes

InChI:InChI=1/C11H8N2/c1-2-6-10-8(4-1)9-5-3-7-12-11(9)13-10/h1-7H,(H,12,13)

Synthetic route

5,6,7,8-tetrahydro-9H-pyrido<2,3-b>indole (7076-11-1) → α-carboline (244-76-8)

Conditions	Yield
With palladium on activated carbon In diphenylether at 210℃; for 0.66h; Inert atmosphere;	97%
With palladium on activated charcoal; diphenylether; biphenyl

8-phenyltetrazolo[1,5-a]pyridine (1130816-42-0) → α-carboline (244-76-8)

Conditions	Yield
With silver hexafluoroantimonate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In benzene at 130℃; for 24h; Solvent; Sealed tube; Glovebox; Inert atmosphere;	96%

3-bromo-N-phenylpyridine-2-amine (54904-02-8) → α-carboline (244-76-8)

Conditions	Yield
With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; tricyclohexylphosphine tetrafluoroborate In N,N-dimethyl acetamide; o-xylene at 145℃; for 16h; Inert atmosphere;	90%
With potassium tert-butylate; ammonia for 1h; Inert atmosphere; Irradiation;	88%
With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; CyJohnPhos In N,N-dimethyl acetamide at 140℃; for 1h; Inert atmosphere;	76%

3-chloro-N-phenyl-2-aminopyridine (6604-94-0) → α-carboline (244-76-8)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane at 180℃; for 0.166667h; Microwave irradiation; sealed tube;	88%
Stage #1: 3-chloro-N-phenyl-2-aminopyridine With palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide for 0.166667h; Graebe-Ullmann Synthesis; Inert atmosphere; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 130℃; for 48h; Graebe-Ullmann Synthesis; Inert atmosphere;	87%
With potassium tert-butylate; ammonia for 1h; Inert atmosphere; Irradiation;	75%

2,2-dimethyl-N-(2-(2-fluoro-3-pyridyl)phenyl)propanamide (146141-05-1) → α-carboline (244-76-8)

Conditions	Yield
With pyridine hydrochloride for 0.25h;	82%
With pyridine hydrochloride for 0.25h; Heating; cyclization of various o-pivaloylaminophenyl-o'-halopyridines;	82%

2,2-dimethyl-N-(2-(2-chloro-3-pyridyl)phenyl)propanamide (146141-06-2) → α-carboline (244-76-8)

Conditions	Yield
With pyridine hydrochloride for 0.25h;	82%

3-(2-nitro-phenyl)-pyridine (4253-80-9) → α-carboline (244-76-8)

Conditions	Yield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; triphenylphosphine In 1,4-dioxane at 55℃; for 96h; Cadogan-Cameron Wood Cyclization; Inert atmosphere; Irradiation;	81%
With 1,10-Phenanthroline; carbon monoxide; palladium diacetate In N,N-dimethyl-formamide at 140℃; under 3102.89 Torr; for 16h;	74%

malondialdehyde bis(diethyl acetal) (122-31-6) + 2-tosylamidoindole (36982-86-2) → α-carboline (244-76-8)

Conditions	Yield
With hydrogen bromide In ethanol at 80 - 100℃; for 1.5h;	76%

9-methoxymethyl-9H-pyrido[2,3-b]indole → α-carboline (244-76-8)

Conditions	Yield
With methanol; trifluorormethanesulfonic acid; trimethyl orthoformate In nitromethane at 100℃; for 1h;	74%

tert-butyl 3-((1E,3Z)-3-(methoxyimino)prop-1-en-1-yl)-1bH-indole-1-carboxylate (1497420-36-6) → α-carboline (244-76-8)

Conditions	Yield
In 1,2-dichloro-benzene at 240℃; for 3h; Sealed tube; Microwave irradiation;	73%

1-phenyl-1H-7-azabenzo[d][1,2,3]triazole (62052-02-2) → α-carboline (244-76-8)

Conditions	Yield
In 1,4-dioxane for 15h; Irradiation;	61%

2-(2-methanesulfonylanilino)-pyridine → benzo[4,5]imidazo[1,2-a]pyridine (245-47-6) + α-carboline (244-76-8)

Conditions	Yield
In tert-butyl alcohol for 4h; Cyclization; Irradiation;	A 3% B 59%

1-(pyridin-2-yl)-1H-benzo[d][1,2,3]triazole (13174-93-1) → α-carboline (244-76-8)

Conditions	Yield
With polyphosphoric acid at 160 - 175℃; for 3h;	47%
With PPA at 150 - 160℃; for 2h;	36%
With pyrophosphoric acid at 170℃; for 0.00833333h; microwave irradiation;	34%

3-(4-trifluoromethylphenyl)-1,2,3-triazolo<4,5-b>pyridine → α-carboline (244-76-8) + 2-aniline-3-hydroxypyridine (92755-42-5) + 1-azacarbazole-6-carboxylic acid + 3-hydroxy-2-anilinopyridine-4'-carboxylic acid

Conditions	Yield
With PPA at 140 - 180℃; for 0.5h;	A 1.4% B 10.6% C 25.4% D 42.5%

ethyl 4-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)benzoate → α-carboline (244-76-8) + 2-aniline-3-hydroxypyridine (92755-42-5) + 1-azacarbazole-6-carboxylic acid + 3-hydroxy-2-anilinopyridine-4'-carboxylic acid

Conditions	Yield
With PPA at 140 - 180℃; for 0.5h;	A 4% B 12.8% C 23.5% D 35%
With PPA at 140 - 180℃; for 0.5h;	A 4% B 12.8% C 23.5% D 35%
With PPA at 140 - 180℃; for 0.5h;	A 4% B 12.8% C 23.5% D 35%

2,3-dichloro-pyridine (2402-77-9) + aniline (62-53-3) → α-carboline (244-76-8)

Conditions	Yield
Stage #1: 2,3-dichloro-pyridine; aniline With palladium diacetate; triphenylphosphine; sodium t-butanolate In o-xylene at 120℃; for 3h; Inert atmosphere; Darkness; Stage #2: With tri-tert-butyl phosphine; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl acetamide; o-xylene at 150℃; for 12h; Inert atmosphere;	33%
Stage #1: 2,3-dichloro-pyridine; aniline With sodium t-butanolate; palladium diacetate; triphenylphosphine In o-xylene at 120℃; for 3h; Inert atmosphere; Stage #2: palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; tricyclohexylphosphine In ISOPROPYLAMIDE; o-xylene at 150℃; for 12h;
Multi-step reaction with 2 steps 1.1: palladium diacetate; triphenylphosphine; sodium t-butanolate / toluene / 0.17 h / 20 Torr / Inert atmosphere 1.2: 16 h / 100 °C / Inert atmosphere 2.1: palladium diacetate; triphenylphosphine / N,N-dimethyl-formamide / 0.17 h / Inert atmosphere 2.2: 48 h / 130 °C / Inert atmosphere View Scheme

2-chloropyridine (109-09-1) + 2-Chloroaniline (95-51-2) → α-carboline (244-76-8)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium tert-butylate In 1,4-dioxane; 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 20h;	10%

3-(2-azidophenyl)pyridine (856849-78-0) + decalin (91-17-8) → γ-carboline (244-69-9) + α-carboline (244-76-8)

Conditions	Yield
at 180℃;

3-(2-azidophenyl)pyridine (856849-78-0) → γ-carboline (244-69-9) + α-carboline (244-76-8)

Conditions	Yield
With decalin at 180℃;

1-(N-L-triptophanyl)-1-deoxy-D-fructose (87251-66-9) → 5-hydroxymethyl-2-furfuraldehyde (67-47-0) + Maltol (118-71-8) + isomaltol (3420-59-5) + α-carboline (244-76-8) + L-Tryptophan (73-22-3)

Conditions	Yield
In water at 95℃; under 750.06 - 450036 Torr; Rate constant; Product distribution; various pressure; ΔV*;

1-benzylpyrazole (10199-67-4) + chloroform (67-66-3) → 2-chloropyrimidine (1722-12-9) + 2-phenylpyrimidine (7431-45-0) + α-carboline (244-76-8)

Conditions	Yield
at 550 - 555℃; Title compound not separated from byproducts;

chloroform (67-66-3) + 1-benzyl-4-chloro-1H-pyrazole (50877-40-2) → 2-phenylpyrimidine (7431-45-0) + 1-benzylpyrazole (10199-67-4) + α-carboline (244-76-8) + 3-chloro-9H-pyrido[2, 3-b]indole

Conditions	Yield
at 550 - 555℃; Further byproducts given. Title compound not separated from byproducts;

1-benzyl-4-chloro-1H-pyrazole (50877-40-2) → NH-pyrazole (288-13-1) + 1-benzylpyrazole (10199-67-4) + α-carboline (244-76-8) + 3-chloro-9H-pyrido[2, 3-b]indole

Conditions	Yield
With chloroform at 550 - 555℃; Further byproducts given. Title compound not separated from byproducts;

1--benztriazole → α-carboline (244-76-8)

Conditions	Yield
With zinc(II) chloride
With phosphoric acid

2-chloropyridine (109-09-1) → α-carboline (244-76-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / 2 h / 150 - 160 °C 2: 36 percent / PPA / 2 h / 150 - 160 °C View Scheme
Multi-step reaction with 2 steps 1: 87 percent / 0.17 h / 180 °C / microwave irradiation 2: 34 percent / H4P2O7 / 0.01 h / 170 °C / microwave irradiation View Scheme

1,2,3-Benzotriazole (95-14-7) → α-carboline (244-76-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / 2 h / 150 - 160 °C 2: 36 percent / PPA / 2 h / 150 - 160 °C View Scheme
Multi-step reaction with 2 steps 1: 5 percent / 0.17 h / 180 °C / microwave irradiation 2: 34 percent / H4P2O7 / 0.01 h / 170 °C / microwave irradiation View Scheme
Multi-step reaction with 2 steps 1: 30 percent / 0.17 h / 180 °C / microwave irradiation 2: 34 percent / H4P2O7 / 0.01 h / 170 °C / microwave irradiation View Scheme

2-bromo-pyridine (109-04-6) → α-carboline (244-76-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 30 percent / 0.17 h / 180 °C / microwave irradiation 2: 34 percent / H4P2O7 / 0.01 h / 170 °C / microwave irradiation View Scheme
Multi-step reaction with 2 steps 1: toluene / 18 h / Reflux 2: polyphosphoric acid / 3 h / 160 - 175 °C View Scheme
Multi-step reaction with 2 steps 1: toluene / Reflux 2: polyphosphoric acid / 160 - 175 °C View Scheme

2-methylsulfanyl-pyridine (18438-38-5) → α-carboline (244-76-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 5 percent / 0.17 h / 180 °C / microwave irradiation 2: 34 percent / H4P2O7 / 0.01 h / 170 °C / microwave irradiation View Scheme

2-Amino-3-bromopyridine (13534-99-1) → α-carboline (244-76-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / t-BuONa; 1,1'-bis(diphenylphosphino)ferrocine / Pd2(dba)3 / toluene / 17 h / 100 °C 2: 31 percent / Na2CO3 / Pd(OAc)2 / dimethylformamide / 67 h / Heating View Scheme
Multi-step reaction with 2 steps 1: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate / tert-butyl alcohol 2: palladium diacetate; C26H35P; 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl acetamide View Scheme
Multi-step reaction with 2 steps 1: palladium diacetate; sodium t-butanolate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 2-methyl-propan-1-ol / 18 h / Reflux 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium diacetate; CyJohnPhos / N,N-dimethyl acetamide / 1 h / 140 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / toluene / 24 h / Reflux 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium diacetate; CyJohnPhos / N,N-dimethyl acetamide / 24 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / toluene / 24 h / Reflux 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium diacetate; CyJohnPhos / N,N-dimethyl acetamide / 24 h / Reflux View Scheme

2,6-diiodo-pyridine (53710-17-1) + α-carboline (244-76-8) → 9-(6-iodopyridin-2-yl)-9H-pyrido[2,3-b]indole

Conditions	Yield
With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine In 1,4-dioxane for 12h; Reflux;	100%

α-carboline (244-76-8) + 1,3-dibromobenzene (108-36-1) → 9-(3-bromophenyl)-9H-pyrido[2,3-b]indole

Conditions	Yield
With potassium phosphate; copper(l) iodide; rac-diaminocyclohexane In toluene for 16h; Reflux;	94%
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide for 24h; Inert atmosphere; Reflux;	68%
With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane In 1,4-dioxane for 36h; Reflux; Inert atmosphere;

2-bromo-pyridine (109-04-6) + α-carboline (244-76-8) → 9-(2-pyridyl)-9H-pyrido<2,3-b>indole

Conditions	Yield
With copper; potassium carbonate at 205℃; for 2h; Irradiation;	93%
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene for 4.5h; Inert atmosphere; Reflux;
Stage #1: 2-bromo-pyridine; α-carboline With palladium diacetate; sodium t-butanolate In toluene for 0.5h; Stage #2: With tri-tert-butyl phosphine In toluene for 4h; Reflux;

α-carboline (244-76-8) + iodobenzene (591-50-4) → 9-phenyl-9H-pyrido<2,3-b>indole

Conditions	Yield
With potassium phosphate; copper(l) iodide; rac-diaminocyclohexane In toluene for 16h; Reflux;	93%
With potassium phosphate; copper(l) iodide; (S,S)-1,2-diaminocyclohexane In 1,4-dioxane for 24h; Reflux;	70%
With copper; potassium carbonate at 200℃; for 5h; Irradiation;	59%
Inert atmosphere;

α-carboline (244-76-8) → 6-bromo-9H-pyrido[2,3-b]indole (26066-88-6)

Conditions	Yield
With N-Bromosuccinimide In dichloromethane at 20℃; Inert atmosphere;	93%
With bromine In dichloromethane at 20℃; for 1h;	91%
With N-Bromosuccinimide In dichloromethane at 20℃; for 2h;	89.7%

α-carboline (244-76-8) + 3,3’-oxybis(iodobenzene) (102391-48-0) → 9,9’-(oxybis(3,1-phenylene))bis(9H-pyrido[2,3-b]indole)

Conditions	Yield
With copper(I) oxide; 4,7-dimethoxy-1,10-phenanthroline; caesium carbonate In dimethyl sulfoxide at 130 - 160℃; Inert atmosphere;	92%

monomethyl oxalyl chloride (5781-53-3) + α-carboline (244-76-8) → C14H10N2O3

Conditions	Yield
With aluminium trichloride In dichloromethane at 20℃;	90%

α-carboline (244-76-8) + 2,7-dibromo-10-phenyl-10H-spiro[acridine-9,9'-fluorene] → 10-phenyl-2,7-bis(9H-pyrido[2,3-b]indol-9-yl)-10H-spiro[acridine-9,9'-fluorene]

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 110℃; for 10h; Buchwald-Hartwig Coupling; Inert atmosphere;	88.5%
With tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate In toluene; tert-butyl alcohol for 12h; Inert atmosphere; Reflux;	88.5%

2,6-dibromopyrazine (23229-25-6) + α-carboline (244-76-8) → C26H16N6

Conditions	Yield
With 1-methyl-1H-imidazole; copper(l) iodide; potassium carbonate In toluene at 120℃; for 16h; Sealed tube; Inert atmosphere;	87%

α-carboline (244-76-8) + but-3-enoic anhydride (1760-48-1) → C16H13NO

Conditions	Yield
With sulfuric acid In dichloromethane at 40℃; for 6h;	86%

α-carboline (244-76-8) → 6-iodo-9H-pyrido [2,3-b]indole (26066-89-7)

Conditions	Yield
Stage #1: α-carboline With acetic acid; potassium iodide for 1h; Reflux; Inert atmosphere; Stage #2: With potassium iodate for 2h; Reflux; Inert atmosphere;	85%

α-carboline (244-76-8) + 2-(2-bromophenyl)-5-phenyl-[1,3,4]oxadiazole (83817-43-0) → C25H16N4O

Conditions	Yield
With copper(l) iodide; potassium carbonate; L-proline In dimethyl sulfoxide at 90℃; for 48h; Inert atmosphere;	84.2%

α-carboline (244-76-8) + 1-{2-[4-(chloromethyl)phenoxy]ethyl}hexahydro-1H-azepine hydrochloride (223251-25-0) → 9-(4-(2-(azepan-1-yl)ethoxy)benzyl)-9H-pyrido[2,3-b]indole

Conditions	Yield
Stage #1: α-carboline With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: 1-{2-[4-(chloromethyl)phenoxy]ethyl}hexahydro-1H-azepine hydrochloride In N,N-dimethyl-formamide at 20℃;	84%

α-carboline (244-76-8) + 1-(2-(4-(chloromethyl)phenoxy)ethyl)pyrrolidine hydrochloride → 9-(4-(2-(pyrrolidin-1-yl)ethoxy)benzyl)-9H-pyrido[2,3-b]indole

Conditions	Yield
Stage #1: α-carboline With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: 1-(2-(4-(chloromethyl)phenoxy)ethyl)pyrrolidine hydrochloride In N,N-dimethyl-formamide at 20℃;	83%

α-carboline (244-76-8) + 4-fluoro-1-iodo-2-methylbenzene (66256-28-8) → C18H13FN2

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 7h; Temperature;	82.5%

α-carboline (244-76-8) → 6-nitro-9H-pyrido[2,3-b]indole (6453-22-1)

Conditions	Yield
With nitric acid In water at 0 - 30℃;	82%
With sulfuric acid; nitric acid In water at -5 - 0℃; for 0.333333h; Inert atmosphere;	78.2%
With sulfuric acid; nitric acid In water at -5 - 0℃; for 0.333333h; Inert atmosphere;	78.2%
With nitric acid
Multi-step reaction with 2 steps 1.1: ceric ammonium nitrate / acetonitrile / 12 h / Heating 1.2: 63 percent / DMAP / acetonitrile / 12 h / 20 °C 2.1: 79 percent / TFA / CH2Cl2 / 2 h / Heating View Scheme

α-carboline (244-76-8) + 2-bromo-4-phenylquinazoline → C25H16N4

Conditions	Yield
With potassium phosphate; copper(l) iodide; rac-diaminocyclohexane In N,N-dimethyl-formamide for 16h; Inert atmosphere; Reflux;	82%

α-carboline (244-76-8) + 4-(2-morpholin-1-yl-ethoxy)benzyl chloride hydrochloride → 4-(2-(4-((9H-pyridyl[2,3-b]indol-9-yl)methyl)phenoxy)ethyl)morpholine

Conditions	Yield
Stage #1: α-carboline With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: 4-(2-morpholin-1-yl-ethoxy)benzyl chloride hydrochloride In N,N-dimethyl-formamide at 20℃;	82%

α-carboline (244-76-8) + 2,6-difluoro pyridine (1513-65-1) → 9-(6-(9H-indeno[2,1-b]pyridin-9-yl)pyridin-2-yl)-9H-pyrido[2,3-b]indole

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 150℃; for 12h; Inert atmosphere;	81%

1-bromo-3,5-dichloro-2,4,6-triazine (854450-65-0) + α-carboline (244-76-8) → C14H7Cl2N5

Conditions	Yield
Stage #1: α-carboline With sodium hydride In tetrahydrofuran; hexane at 20℃; for 1h; Inert atmosphere; Stage #2: 2-bromo-4,6-dichloro-1,3,5-triazine In tetrahydrofuran; hexane at 20℃; Inert atmosphere;	81%

α-carboline (244-76-8) + 2,8-dibromo-5H-5λ6-dibenzo[b,d]thiophene-5,5-dione (40307-15-1) → 2,8-bis(9H-pyrido[2,3-b]indol-9-yl)dibenzo[b,d]thiophene 5,5-dioxide

Conditions	Yield
With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine In toluene for 12h; Inert atmosphere; Reflux;	80%

α-carboline (244-76-8) + 3,5-difluoropyridine-2-carbonitrile (298709-29-2) → C28H16N6

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 140℃; for 12h; Inert atmosphere;	80%

α-carboline (244-76-8) + 6-bromo-9H-pyrido[2,3-b]indole (26066-88-6) → C22H14N4

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene for 6h; Inert atmosphere; Reflux;	78.9%

Upstream product

• 7076-11-1 5,6,7,8-tetrahydro-9H-pyrido<2,3-b>indole 
• 856849-78-0 3-(2-azidophenyl)pyridine 
• 91-17-8 decalin 
• 62052-02-2 1-phenyl-1H-7-azabenzo[d][1,2,3]triazole 
• 10199-67-4 1-benzylpyrazole 
• 67-66-3 chloroform 
• 54904-02-8 3-bromo-N-phenylpyridine-2-amine 
• 4253-80-9 3-(2-nitro-phenyl)-pyridine 
• 13174-93-1 1-(pyridin-2-yl)-1H-benzo[d][1,2,3]triazole 
• 109-09-1 2-chloropyridine 
• 18438-38-5 2-methylsulfanyl-pyridine 
• 13534-99-1 2-Amino-3-bromopyridine 
• 372-48-5 2-fluoropyridine 
• 78607-36-0 2-chloro-3-iodopyridine 

Downstream Products

• 111032-63-4 1-(3-trimethylammonio-propyl)-9H-pyrido[2,3-b]indolium; dibromide 
• 79960-47-7 9-benzoyl-α-carboline 
• 26066-88-6 6-bromo-9H-pyrido[2,3-b]indole 
• 94718-66-8 1-azacarbazole-6-carboxylic acid 
• 1402414-65-6 9-(9-tosyl-carbazol-3-yl)-pyrido[2,3-b]indole 
• 1374147-31-5 9-(4-bromobenzene)-9H-pyridin[2,3-b]indole 
• 1466608-45-6 9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-pyrido [2,3-b] indole 
• 1600515-44-3 N-o-tolyl-9H-pyrido[2,3-b]indol-4-amine 
• 1214220-18-4 (3-nitrophenyl)-(9H-pyrido[2,3-b]indol-4-yl)amine 
• 1600515-52-3 C₁₈H₁₅N₃O 
• 1600515-53-4 N-(4-chlorophenyl)-9H-pyrido[2,3-b]indol-amine 
• 1600515-54-5 C₁₈H₁₄ClN₃ 
• 1600515-55-6 C₁₇H₁₁ClFN₃ 
• 1600515-56-7 C₂₄H₁₈ClN₃O 

Relevant academic research and scientific papers

Synthesis of 6-substituted pyrido[2,3-b]indoles by electrophilic substitution

Regioselective electrophilic aromatic substitutions, acylation, bromination, and formylation, of unprotected pyrido[2,3-b]indole (α-carbolines) at the C-6 position are described. Alternative conditions for the nitration were investigated, which led to the unexpected appearance of the minor C-8 isomer. Georg Thieme Verlag Stuttgart.

Method for preparing 9H-pyrido[2,3-B]indole

The invention belongs to the technical field of organic chemical synthesis, and particularly relates to a method for preparing 9H-pyrido[2,3-b]indole. Existing preparation methods of the 9H-pyrido[2,3-b]indole are relatively complex in process and relatively low in yield. According to the method for preparing 9H-pyrido[2,3-b]indole in the invention, benzotriazole and 2-bromopyridine are used as raw materials, a substitution reaction of benzotriazole is conducted in a xylene solvent, and then nitrogen removal rearrangement under the action of acid is carried out to obtain the 9H-pyrido[2,3-b]indole. The method is simple in reaction, easy to operate, high in yield, simple in post-treatment, less in wastewater and friendlier to environment.

Convenient One-Pot Synthesis of 9 H -Carbazoles by Microwave Irradiation Employing a Green Palladium-Based Nanocatalyst

An efficient palladium-catalyzed tandem reaction for the one-pot synthesis of 9 H -carbazoles under microwave irradiation is developed. This approach involves a sequential Buchwald-Hartwig amination and a direct arylation from affordable and inexpensive anilines and 1,2-dihaloarenes. For the development of this purpose, a novel and magnetically recoverable palladium nanocatalyst supported on a green biochar under ligand-free conditions is used. Compared to other existing palladium-based protocols, the present synthetic methodology shows a drastic reduction in reaction times and excellent compatibility with different functional groups allowing to obtain a small library of 9 H -carbazoles in high yields and with good regioselectivity. This procedure represents the first example in the direct synthesis of carbazoles using a heterogeneous palladium nanocatalyst from commercial precursors. To examine the application of this protocol, a direct and scalable synthesis of the bioactive carbazole alkaloid clausenalene from commercially available starting materials is described.

Visible-light-driven Cadogan reaction

Visible-light-driven photochemical Cadogan-type cyclization has been discovered. The organic D-A type photosensitizer 4CzIPN found to be an efficient mediator to transfer energy from photons to the transient intermediate that breaks the barriers of deoxygenation in Cadogan reaction and enables a mild metal-free access to carbazoles and related heterocycles. DFT calculation results indicate mildly endergonic formation of the intermediate complex of nitrobiarenes and PPh3, which corresponds with experimental findings regarding reaction temperature. The robust synthetic capacity of the photoredox Cadogan reaction systems has been demonstrated by the viable productivity of a broad range of carbazoles and related N-heterocycles with good tolerance of various functionalities.

Compound and application thereof in field of organic light emitting

The invention relates to a compound. The structure of the compound is shown in a following formula (the formula is shown in the description), wherein L1 and L2 are respectively independently selectedfrom single-bond, substituted or unsubstituted arylidene or fused ring sub-aromatic hydrocarbon group containing C6 to C60, and substituted or unsubstituted heteroarylidene or fused heterocyclic sub-aromatic hydrocarbon group containing one or multiple heteroatoms and C5 to C60; Ar1 and Ar2 are respectively independently selected from substituted or unsubstituted arylidene or fused ring aromatic hydrocarbon group containing C6 to C60, and substituted or unsubstituted heteroaryl, arylamine group, secondary amine group or fused heterocyclic aromatic hydrocarbon group containing one or multiple heteroatoms and C5 to C60; at least one of Ar1 and Ar2 is a electron-deficient group. The invention also provides an organic electroluminescence device adopting the novel compound shown in the formula.The organic electroluminescence device has the advantages that the drive voltage is low, and the light emitting efficiency is high.

Anthraquinone organic electroluminescent material and application thereof

The invention discloses an anthraquinone organic electroluminescent material and application thereof. A general formula compound is shown in a formula (1) in the specification, and in the formula (1),Z is selected from O or S; X1-X8 are independently selected from CR1 or N, wherein R1 is selected from a structure shown in a formula (2) in the specification, or selected from hydrogen, alkyl, arylor heterocyclic aryl, adjacent R1 groups can form a ring, and at least one of R1 groups is selected from the structure (2) shown in the formula (2); in the formula (2), Y1-Y8 are independently selected from CR2 or N, and at least one of the Y1-Y8 is selected from N; R2 is selected from hydrogen, alkyl, aryl or heterocyclic aryl, and adjacent R2 groups can form a ring; L is selected from single bonds, arylidene or heterocyclic arylidene; and when two or more R1 groups are selected from the formula (2), the selected L groups in the formula (2) are not single bonds at the same time. The compoundshows excellent device performance and stability when serving as the light-emitting material in an organic light-emitting device (OLED), and meanwhile the OLED adopting the general formula compound iswithin the scope of right protection.

ORGANIC COMPOUNDS, LIGHE EMITTING DIODE AND LIGHT EMITTING DEVICE HAVING THE COMPOUNDS

The present invention relates to an organic compound having an amine core substituted with three aromatic rings, wherein a part of the three aromatic rings is substituted with a functional group capable of a solution process while the rest of the three aromatic rings is substituted with a hetero-aromatic functional group; and a light-emitting diode and a light-emitting device having the organic compound applied to a light-emitting layer. The organic compound may be used to the light-emitting layer to eliminate the HOMO energy barrier between the light-emitting layer and another light-emitting layer adjacent thereto. Also, the organic compound, when it forms a light-emitting layer in combination with light-emitting particles, may improve interfacial properties between the light-emitting layer and an adjacent layer to improve morphological properties of the light-emitting diode. The organic compound of the present invention, by allowing holes and electrons to be transported and implanted into a light emitting material layer in a balanced manner, may implement light-emitting diodes and light-emitting devices with improved luminance efficiency and capable of low-voltage driving.(110) First electrode(120) Second electrode(AA) Smooth interface morphology ↑COPYRIGHT KIPO 2019

ORGANIC ELECTROLUMINESCENT MATERIALS CONTAINING CARBOLINE GROUP AND ORGANIC ELECTROLUMINESCENT DEVICE BY USING THE SAME

An organic electroluminescent material is shown in General Formula (1), wherein R3 is a carboline group, R13 is a carbazole group or a carboline group, R1 to R2, R4 to R12 and R14 to R20 are each independently selected from the group consisting of a hydrogen atom, a fluorine atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a haloalkyl group, a thioalkyl group, a silyl group and an alkenyl group.

Organic electroluminescent material and device

The invention provides an organic compound with a specific structure. The organic compound is characterized by being shown as a general formula (I): the formula (I) is shown in the description; in theformula (I), X1 to X8 are respectively independently selected from CR1 or N respectively, wherein at least one is an N atom; L is a single bond and is C5 to C12 substituted or unsubstituted arylene and heteroarylene; R1 is selected from hydrogen, C1 to C10 aryl or cycloalkyl, C6 to C15 aryl or C6 to C19 condensed ring aryl and at least one is azacarbazole; Ar is substituted or unsubstituted N heterophenyl. The invention discloses an inverse intersystem crossing constant and emission delayed fluorescence rule and the designed compound is used for an organic electroluminescent device, can be used for effectively improving the current efficiency and is an organic electroluminescent material with good performance. The invention also provides the organic electroluminescent device adopting thecompound shown as the general formula.

Organic compound and Organic light emitting diode and organic emitting display device including the same

The present invention provides an organic compound represented by the following chemical formula 1 and having high thermal stability and triplet energy and excellent hole mobility. An organic light emitting diode and an organic light emitting display device in which such organic compound is used for a hole transport layer and/or a P-type charge generation layer have advantages in driving voltage, light emitting efficiency and lifetime.COPYRIGHT KIPO 2018