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Conditions | Yield |
---|---|
In toluene for 1h; Heating; | 96% |
Conditions | Yield |
---|---|
With tetraphosphorus decasulfide In pyridine at 85℃; for 0.0833333h; | 90% |
Multi-step reaction with 2 steps 1: PCl5 / benzene / 4 h / Heating 2: 70 percent / thiophenol / benzene / 4 h / Heating; further thiophenols used: 1) p-CH3C6H4SH, 2) p-ClC6H4SH, 3) m-CH3C6H4SH, 4) o-CH3C6H4SH View Scheme | |
Multi-step reaction with 2 steps 1: benzene; phosphorus pentachloride 2: zinc dust; glacial acetic acid View Scheme |
1-acetyl-2,3-dihydro-1H-indol-3-one
N,O-diacetylindoxyl
A
1,2-diacetyl-3-indolinone
B
1H,1H'-2,2'-Biindolylidene-3,3'-dione
Conditions | Yield |
---|---|
With sulfuric acid In acetic anhydride at 20℃; for 20h; | A 88.8% B n/a |
1-acetyl-2-propionyl-3-indolinone
A
1-(3-Hydroxy-1H-indol-2-yl)-propan-1-one
B
1H,1H'-2,2'-Biindolylidene-3,3'-dione
Conditions | Yield |
---|---|
With sodium hydroxide at 20℃; for 2h; | A 86.4% B n/a |
1,2-diacetyl-3-indolinone
A
1-(3-Hydroxy-1H-indol-2-yl)ethanon
B
1H,1H'-2,2'-Biindolylidene-3,3'-dione
Conditions | Yield |
---|---|
With sodium hydroxide at 20℃; for 2h; | A 85.7% B n/a |
N,O-diacetylindoxyl
propionic acid anhydride
A
1-acetyl-2-propionyl-3-indolinone
B
1H,1H'-2,2'-Biindolylidene-3,3'-dione
Conditions | Yield |
---|---|
With sulfuric acid In acetic anhydride | A 72% B n/a |
Conditions | Yield |
---|---|
With thiophenol In benzene for 4h; Heating; further thiophenols used: 1) p-CH3C6H4SH, 2) p-ClC6H4SH, 3) m-CH3C6H4SH, 4) o-CH3C6H4SH; | 70% |
With hydrogen iodide; acetic acid | |
With acetic acid; zinc | |
With ammonium sulfide | |
With phosphorous |
1-acetyl-2-benzoyl-3-indolinone
A
2-benzoyl-3-hydroxyindole
B
1H,1H'-2,2'-Biindolylidene-3,3'-dione
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 20℃; for 20h; | A 67.8% B n/a |
1-(phenylsulfonyl)-2-trimethylsilylindol-3-yl trifluoromethanesulfonate
1H,1H'-2,2'-Biindolylidene-3,3'-dione
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran | 51% |
2,3-dioxo-2,3-dihydro-1H-indole-5-sulfonate
A
1H,1H'-2,2'-Biindolylidene-3,3'-dione
Conditions | Yield |
---|---|
With N,N'-bis(6A-deoxy-β-cyclodextrin-6A-yl)NHCOCONH In water at 20℃; pH=10.0; Product distribution; Further Variations:; Reagents; | A 1.8% B 36% |
Conditions | Yield |
---|---|
at 300℃; for 2h; spray vacuum pyrolysis; | 15% |
Conditions | Yield |
---|---|
With potassium hydroxide; sodium hydroxide; sodium amide at 200℃; Reaktion ueber mehrere Stufen; |
pyridine
indolin-3-one
2-chloro-3H-indol-3-one
1H,1H'-2,2'-Biindolylidene-3,3'-dione
indole
Perbenzoic acid
chloroform
A
N-formyl-2-aminobenzaldehyde
B
1H,1H'-2,2'-Biindolylidene-3,3'-dione
indole
Perbenzoic acid
A
N-formyl-2-aminobenzaldehyde
B
1H,1H'-2,2'-Biindolylidene-3,3'-dione
Conditions | Yield |
---|---|
With chloroform |
Conditions | Yield |
---|---|
With air; sodium sulfite | |
With air; sodium hydrogensulfite | |
With dihydrogen peroxide; sodium hydrogencarbonate |
Conditions | Yield |
---|---|
With soda lime; methyllithium; calcium carbonate; zinc | |
Multi-step reaction with 5 steps 1: H2 / Pd-C 2: aq NaNO2, 1:1 dil aq HCl / 0 °C 3: aq NaN3/NaOAc / 0.17 h 4: xylene / Heating 5: 15 percent / 2 h / 300 °C / spray vacuum pyrolysis View Scheme | |
Multi-step reaction with 4 steps 1: H2 / Pd-C 2: aq NaNO2, 1:1 dil aq HCl / 0 °C 3: aq NaN3/NaOAc / 0.17 h 4: 0.5 g / 2 h / 300 °C / spray vacuum pyrolysis View Scheme |
2-chloro-3H-indol-3-one
A
1H,1H'-2,2'-Biindolylidene-3,3'-dione
B
indirubin
Conditions | Yield |
---|---|
With acetic acid; zinc |
2-formyl-3-hydroxyindole
1H,1H'-2,2'-Biindolylidene-3,3'-dione
Conditions | Yield |
---|---|
Oxydieren; |
1H-indole-3-carboxylic acid
A
anthranilic acid
B
1H,1H'-2,2'-Biindolylidene-3,3'-dione
Conditions | Yield |
---|---|
With sodium hydroxide; ozone; acetone |
3-hydroxy-1H-indole-2-carboxylic acid
3-(2-nitrophenyl)-2-propynoic acid
1H,1H'-2,2'-Biindolylidene-3,3'-dione
Conditions | Yield |
---|---|
With sodium carbonate |
1-hydroxy-1H-indole-2-carboxylic acid
1H,1H'-2,2'-Biindolylidene-3,3'-dione
Conditions | Yield |
---|---|
With sulfuric acid |
2'-nitro-chalcone
A
benzaldehyde
B
benzoic acid
C
1H,1H'-2,2'-Biindolylidene-3,3'-dione
Conditions | Yield |
---|---|
Sonnenlicht; |
Conditions | Yield |
---|---|
With hydrogen sulfide |
D-glucose
2-Nitrobenzoylessigsaeure
1H,1H'-2,2'-Biindolylidene-3,3'-dione
β-(2-Nitrophenyl)-β-propiolacton
acetic acid
1H,1H'-2,2'-Biindolylidene-3,3'-dione
1-nitro-2-(2-nitrovinyl)benzene
1H,1H'-2,2'-Biindolylidene-3,3'-dione
Conditions | Yield |
---|---|
With sodium dithionite |
Conditions | Yield |
---|---|
With hydrogen sulfide; sodium carbonate | |
With potassium xanthate; water; potassium carbonate | |
With D-glucose |
Conditions | Yield |
---|---|
With copper; potassium carbonate In 1,2-dichloro-benzene for 10h; Heating; | 91.7% |
Conditions | Yield |
---|---|
With potassium dichromate; sulfuric acid In water at 40 - 45℃; for 1.5h; | 90% |
With sodium hydroxide Erwaermen des Reaktionsprodukts mit Salpetersaeure (15%ig) die Chromsaeure enthaelt, nach Filtern und den Rueckstand in Natronlauge Loesen und Behandeln mit Saeure; | |
With nitric acid | |
With chromic acid | |
With oxygen; methylene blue In dimethylsulfoxide-d6 for 8h; Irradiation; |
di-tert-butyl dicarbonate
1H,1H'-2,2'-Biindolylidene-3,3'-dione
Conditions | Yield |
---|---|
With dmap In dichloromethane at 20℃; for 48h; Inert atmosphere; | 90% |
With dmap In dichloromethane at 20℃; | 89% |
With dmap In N,N-dimethyl-formamide at 20℃; for 20h; | 85.2% |
acetic acid
1H,1H'-2,2'-Biindolylidene-3,3'-dione
2,2'-diacetoxy-1,2,1',2'-tetrahydro-[2,2']biindolyl-3,3'-dione
Conditions | Yield |
---|---|
With potassium permanganate at 20℃; | 88% |
With lead dioxide | |
With manganese(IV) oxide |
acetic anhydride
1H,1H'-2,2'-Biindolylidene-3,3'-dione
1H,1'H-2,2'-bisindol-3-yl acetate
Conditions | Yield |
---|---|
With tin; acetic acid at 64 - 66℃; reductive acetylation; | 88% |
With tin In acetic acid at 64 - 66℃; | 85% |
With tin; acetic acid at 64 - 66℃; for 3h; | 85% |
With iron; acetic acid at 64 - 66℃; for 2.5h; | 82% |
acetic anhydride
1H,1H'-2,2'-Biindolylidene-3,3'-dione
A
2,2'-biindole
B
1H,1'H-2,2'-bisindol-3-yl acetate
Conditions | Yield |
---|---|
With tin In acetic acid at 64 - 66℃; for 2.5h; | A 1% B 88% |
acetic anhydride
1H,1H'-2,2'-Biindolylidene-3,3'-dione
A
2,2'-biindole
B
1-acetyl-2,3-dihydro-2,2'-bisindole
C
1H,1'H-2,2'-bisindol-3-yl acetate
Conditions | Yield |
---|---|
With acetic acid; zinc at 60 - 62℃; for 8h; | A 3% B 82% C 3% |
With zinc In acetic acid at 60 - 62℃; for 8h; | A 3% B 82% C 3% |
With zinc In acetic acid at 49 - 52℃; for 8h; Product distribution; var. metal, temp., time, atm.; | A 46% B 21% C 18% |
4-iodo-benzoic acid hexyl ester
1H,1H'-2,2'-Biindolylidene-3,3'-dione
Conditions | Yield |
---|---|
With copper; potassium carbonate In 1,2-dichloro-benzene for 17h; Heating; | 80.7% |
1H,1H'-2,2'-Biindolylidene-3,3'-dione
dibenzo{b,g}{1,5}-naphthiridin-6,12(5,11H)-dione
Conditions | Yield |
---|---|
In gas at 460℃; | 80% |
2-propynyl chloride
1H,1H'-2,2'-Biindolylidene-3,3'-dione
B
6-methylene-6,7-dihydropyrazino[1,2-a:4,3-a']diindole-13,14-dione
Conditions | Yield |
---|---|
Stage #1: 1H,1H'-2,2'-Biindolylidene-3,3'-dione With caesium carbonate In N,N-dimethyl-formamide at 88℃; for 1h; Inert atmosphere; Molecular sieve; Stage #2: 2-propynyl chloride In N,N-dimethyl-formamide for 0.0833333h; Inert atmosphere; Molecular sieve; Cooling with ice; | A 3% B 79% |
Conditions | Yield |
---|---|
With copper; potassium carbonate In 1,2-dichloro-benzene for 10h; Heating; | 73.8% |
allyl bromide
1H,1H'-2,2'-Biindolylidene-3,3'-dione
A
8H,16H-pyrido[1,2,3-s,t]-indolo[1,2-a]azepino[3,4-b]indol-17-one
B
1-allyl-10'-allyloxy-2'H-spiro(indoline-2,1'-pyrido[1,2-a]indol)-3-one
Conditions | Yield |
---|---|
Stage #1: 1H,1H'-2,2'-Biindolylidene-3,3'-dione In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Sonication; Stage #2: With caesium carbonate In N,N-dimethyl-formamide at 85 - 88℃; for 0.5h; Inert atmosphere; Molecular sieve; Stage #3: allyl bromide In N,N-dimethyl-formamide at 85 - 88℃; for 3h; Inert atmosphere; Molecular sieve; | A 72% B 15% |
Conditions | Yield |
---|---|
In pyridine at 45℃; for 2h; | 70% |
With sodium hydride 1.) HMPA, 0 deg C, 4 h, 2.) HMPA, 15 h; Yield given. Multistep reaction; |
2-methyl-3-bromo-1-propene
1H,1H'-2,2'-Biindolylidene-3,3'-dione
A
7,15-dimethyl-8H,16H-pyrido[1,2,3-s,t]-indolo[1,2-a]azepino[3,4-b]indol-17-one
B
3'-methyl-1-[3-(2-methyl)prop-1-enyl]-10'-[3-(2-methyl)-prop-1-enyl]oxy-2'H-spiro(indoline-2,1'-pyrido[1,2-a]indol)-3-one
Conditions | Yield |
---|---|
Stage #1: 1H,1H'-2,2'-Biindolylidene-3,3'-dione In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Sonication; Stage #2: With caesium carbonate In N,N-dimethyl-formamide at 85 - 88℃; for 0.5h; Inert atmosphere; Molecular sieve; Stage #3: 2-methyl-3-bromo-1-propene In N,N-dimethyl-formamide at 85 - 88℃; for 3h; Inert atmosphere; Molecular sieve; | A 69% B 15% |
pyridine-3-carbonyl chloride hydrochloride
1H,1H'-2,2'-Biindolylidene-3,3'-dione
N,N'-dinicotinoyl-2,2'-bi-indolinylidene-3,3'-dione
Conditions | Yield |
---|---|
With pyridine at 50℃; for 5h; | 68% |
phthalocyaninatotin(II)
tetrabutylammomium bromide
1,2-dichloro-benzene
1H,1H'-2,2'-Biindolylidene-3,3'-dione
Conditions | Yield |
---|---|
Stage #1: phthalocyaninatotin(II); tetrabutylammomium bromide; 1,2-dichloro-benzene; 1H,1H'-2,2'-Biindolylidene-3,3'-dione With fluorenone radical anion sodium contact ion pair at 80℃; for 24h; Stage #2: μ-diiodo-di((η5-pentamethylcyclopentadienyl)(iodo)iridium) at 80℃; for 24h; | 67% |
1H,1H'-2,2'-Biindolylidene-3,3'-dione
d2-indigo
Conditions | Yield |
---|---|
With pyridine; d(4)-methanol for 12h; 1.)reflux, 2 h 2.)20 deg C, 12 h; | 66.2% |
(E)-1-Bromo-2-butene
1H,1H'-2,2'-Biindolylidene-3,3'-dione
Conditions | Yield |
---|---|
Stage #1: 1H,1H'-2,2'-Biindolylidene-3,3'-dione In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Sonication; Stage #2: With caesium carbonate In N,N-dimethyl-formamide at 85 - 88℃; for 0.5h; Inert atmosphere; Molecular sieve; Stage #3: (E)-1-Bromo-2-butene In N,N-dimethyl-formamide at 85 - 88℃; for 3h; Inert atmosphere; Molecular sieve; | 65% |
Conditions | Yield |
---|---|
Stage #1: 1H,1H'-2,2'-Biindolylidene-3,3'-dione With caesium carbonate In N,N-dimethyl-formamide at 85℃; for 0.5h; Inert atmosphere; Stage #2: 1-Bromo-2-butyne In N,N-dimethyl-formamide at 85℃; for 0.0666667h; Inert atmosphere; | 65% |
1,2-dichloro-benzene
[2.2.2]cryptande
1H,1H'-2,2'-Biindolylidene-3,3'-dione
Conditions | Yield |
---|---|
With potassium graphite at 80℃; Inert atmosphere; Glovebox; | 63% |
Conditions | Yield |
---|---|
Stage #1: 1H,1H'-2,2'-Biindolylidene-3,3'-dione In N,N-dimethyl-formamide for 0.5h; Inert atmosphere; Sonication; Stage #2: With caesium carbonate In N,N-dimethyl-formamide at 85 - 88℃; for 0.5h; Inert atmosphere; Stage #3: 2-methyl-3-bromo-1-propene In N,N-dimethyl-formamide for 0.00138889h; Time; Inert atmosphere; | A 7% B 62% |
Conditions | Yield |
---|---|
With copper; potassium carbonate In 1,2-dichloro-benzene for 13h; Heating; | 60% |
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