Alternatived Products of [ 3449-50-1 ]
Product Details of [ 3449-50-1 ]
| CAS No. : | 3449-50-1 |
MDL No. : | MFCD16090101 |
| Formula : |
C13H13NO
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | MYXBAASANSTUBM-UHFFFAOYSA-N |
| M.W : | 199.25 |
Pubchem ID : | 11769501 |
| Synonyms : |
|
Application In Synthesis of [ 3449-50-1 ]
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
- Downstream synthetic route of [ 3449-50-1 ]
- 1
-
[ 3449-50-1 ]
-
8-methyl-6-nitro-2,3,4,9-tetrahydro-carbazol-1-one
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
With sulfuric acid; potassium nitrate at -5℃; |
|
- 2
-
[ 2257-18-3 ]
-
[ 3449-50-1 ]
| Yield | Reaction Conditions | Operation in experiment |
| 50% |
With acide sulfurique In ethanol for 3.5h; Heating; |
|
|
With hydrogenchloride; water; acetic acid |
|
|
With hydrogenchloride; acetic acid In water |
|
|
With sulfuric acid In water; acetonitrile for 4h; Reflux; |
2,3,4,9-tetrahydro-1H-carbazol-1-one (3)
General procedure: To a 100mL round-bottom bottle equipped with a condenser was added phenylhydrazone 2(10mmol), sulfuric acid solution (16.7mL, 1.8M) and 40mL of acetonitrile. The mixture was heated to reflux and kept for 4h and then the reaction was quenched with 30mL of cold water. The precipitate wasfiltered and washed with water after aging 1h . A brown solid was obtained after dry in 58% yield. |
Reference：
[1]Bisagni, Emile; Ducrocq, Claire; Hung, Nguyen Chi
[Tetrahedron, 1980, vol. 36, # 10, p. 1327 - 1330]
[2]Anderson; Campbell
[Journal of the Chemical Society, 1950, p. 2855]
Mears; Oakeshott; Plant
[Journal of the Chemical Society, 1934, p. 272,275]
[3]Shanmugasundaram, Kandasamy; Rajendra Prasad, Karnam J.
[Heterocycles, 1999, vol. 51, # 9, p. 2163 - 2169]
[4]Wu, Zhijie; Li, Ying; Cai, Yu; Yuan, Junying; Yuan, Chengye
[Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 17, p. 4903 - 4906]
- 3
-
[ 3449-50-1 ]
-
[ 4774-33-8 ]
-
[ 132906-63-9 ]
| Yield | Reaction Conditions | Operation in experiment |
| 60% |
With toluene-4-sulfonic acid In formamide at 185℃; for 7h; |
|
- 4
-
[ 3449-50-1 ]
-
[ 6510-65-2 ]
- 5
-
[ 3449-50-1 ]
-
1-Hydroxyimino-8-methyl-1,2,3,4-tetrahydrocarbazole
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 70% |
With pyridine; hydroxylamine hydrochloride In ethanol for 1h; Heating; |
|
- 6
-
[ 2257-18-3 ]
-
[ 3449-50-1 ]
| Yield | Reaction Conditions | Operation in experiment |
| 52% |
With hydrogenchloride; acetic acid for 0.0333333h; Heating; |
|
- 7
-
[ 3449-50-1 ]
-
[ 141-43-5 ]
-
2-[8-Methyl-2,3,4,9-tetrahydro-carbazol-(1E)-ylideneamino]-ethanol
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 60% |
In methanol for 1h; Heating; |
|
- 8
-
[ 3449-50-1 ]
-
[ 73910-78-8 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With palladium on activated charcoal In diphenylether |
|
|
With palladium on activated charcoal |
|
Reference：
[1]Shanmugasundaram, Kandasamy; Rajendra Prasad, Karnam J.
[Heterocycles, 1999, vol. 51, # 9, p. 2163 - 2169]
[2]Location in patent: body text
Yamuna, Ezhumalai; Zeller, Matthias; Rajendra Prasad, Karnam Jayarampillai
[Tetrahedron Letters, 2011, vol. 52, # 45, p. 6030 - 6034]
- 9
-
[ 3449-50-1 ]
-
[ 551-93-9 ]
-
1,7-dimethyl-13<i>H</i>-indolo[3,2-<i>c</i>]acridine
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 68% |
With air; sulfuric acid In acetic acid for 8h; Heating; |
|
- 10
-
[ 3449-50-1 ]
-
[ 59-88-1 ]
-
1-Methyl-5,6,11,12-tetrahydroindolo[2,3-a]carbazole
[ No CAS ]
-
8-Methyl-1-phenylhydrazono-1,2,3,4-tetrahydrocarbazole
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 63% |
In ethanol for 4h; Heating; |
|
- 11
-
[ 3449-50-1 ]
-
[ 100-63-0 ]
-
1-Methyl-5,6,11,12-tetrahydroindolo[2,3-a]carbazole
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 70% |
With acetic acid for 3h; Heating; |
|
- 12
-
[ 98-03-3 ]
-
[ 3449-50-1 ]
-
8-methyl-2-thienyl-1-oxo-1,2,3,4-tetrahydrocarbazole
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 78% |
With potassium hydroxide In ethanol at 20℃; for 8h; |
|
- 13
-
[ 3449-50-1 ]
-
[ 100-52-7 ]
-
2-benzylidene-8-methyl-1-oxo-1,2,3,4-tetrahydrocarbazole
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 80% |
With potassium hydroxide In ethanol at 20℃; for 6h; |
|
- 14
-
[ 3449-50-1 ]
-
[ 64-19-7 ]
-
6-acetyl-8-methyl-2,3,4,9-tetrahydro-carbazol-1-one
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 72% |
With PPA at 100℃; for 8h; |
|
- 15
-
[ 120-57-0 ]
-
[ 3449-50-1 ]
-
8-methyl-2-(3',4'-methylenedioxy)benzylidene-1-oxo-1,2,3,4-tetrahydrocarbazole
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 82% |
With potassium hydroxide In ethanol at 20℃; for 48h; |
|
- 16
-
[ 3449-50-1 ]
-
[ 66-77-3 ]
-
8-Methyl-2-[1-naphthalen-1-yl-meth-(E)-ylidene]-2,3,4,9-tetrahydro-carbazol-1-one
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 78% |
With potassium hydroxide at 20℃; for 6h; |
|
- 17
-
[ 1121-60-4 ]
-
[ 3449-50-1 ]
-
8-Methyl-2-[1-pyridin-2-yl-meth-(E)-ylidene]-2,3,4,9-tetrahydro-carbazol-1-one
[ No CAS ]
-
2-(hydroxy-pyridin-2-yl-methyl)-8-methyl-2,3,4,9-tetrahydro-carbazol-1-one
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 1: 39%
2: 38% |
With sodium hydroxide In ethanol at 20℃; for 1h; |
|
- 18
-
[ 3449-50-1 ]
-
[ 109-94-4 ]
-
[ 248246-37-9 ]
| Yield | Reaction Conditions | Operation in experiment |
| 75% |
Stage #1: 8-methyl-2,3,4,9-tetrahydro-carbazol-1-one; formic acid ethyl ester With sodium hydride In benzene at 20℃; for 30h;
Stage #2: With sodium acetate; acetic anhydride at 170℃; for 10h; |
|
- 19
-
[ 3449-50-1 ]
-
[ 1885-29-6 ]
-
1-methyl-12,13-dihydro-indolo[3,2-<i>c</i>]acridin-7-one
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 75% |
With toluene-4-sulfonic acid In toluene for 6h; Heating; |
|
- 20
-
[ 3449-50-1 ]
-
[ 616-38-6 ]
-
8-methyl-2-ethylidene-3,4-dihydrocarbazol-1(2H)-one
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 80% |
With ethanol; sodium hydride In benzene for 24h; |
|
- 21
-
[ 108-05-4 ]
-
[ 3449-50-1 ]
-
8-methyl-1-oxo-2-(3-methyl-1-oxoprop-3-yl)-1,2,3,4-tetrahydrocarbazole
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 80% |
With potassium hydroxide In ethanol for 24h; |
|
- 22
-
[ 3449-50-1 ]
-
9-methyl-2-(8-methyl-4,9-dihydro-3<i>H</i>-carbazol-1-yloxy)-3,4,5,10-tetrahydro-azepino[2,3-<i>b</i>]indole
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 68% |
With formic acid; hydroxylamine hydrochloride for 11h; Heating; |
|
- 23
-
[ 3449-50-1 ]
-
[ 156424-64-5 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With pyridine; hydroxylamine hydrochloride In ethanol |
|
- 24
-
[ 3449-50-1 ]
-
[ 2835-77-0 ]
-
[ 1027365-23-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 64% |
With sulfuric acid; acetic acid for 8h; Heating; |
|
- 25
-
[ 3449-50-1 ]
-
[ 62-53-3 ]
-
[ 1027365-33-8 ]
| Yield | Reaction Conditions | Operation in experiment |
| 45% |
With toluene-4-sulfonic acid In o-xylene for 10h; Heating; |
|
- 26
-
[ 3449-50-1 ]
-
[ 1027365-28-1 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 64 percent / acetic acid; sulfuric acid / 8 h / Heating
2: 68 percent / Pd/C / diphenyl ether / Heating |
|
- 27
-
[ 3449-50-1 ]
-
[ 1027365-37-2 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 45 percent / p-toluenesulfonic acid / o-xylene / 10 h / Heating
2: 45 percent / POCl3 / 4 h / 20 °C |
|
- 28
-
[ 3449-50-1 ]
-
1,13-dimethyl-7-phenylindolo[3,2-c]acridine
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: 64 percent / acetic acid; sulfuric acid / 8 h / Heating
2: 68 percent / Pd/C / diphenyl ether / Heating
3: 48 percent / K2CO3 / acetone / Heating |
|
- 29
-
[ 3449-50-1 ]
-
1,13-dimethylindolo[3,2-c]acridine
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: 45 percent / p-toluenesulfonic acid / o-xylene / 10 h / Heating
2: 45 percent / POCl3 / 4 h / 20 °C
3: 53 percent / K2CO3 / acetone / Heating |
|
- 30
-
[ 3449-50-1 ]
-
3-acetoxy-2,3,3a,4,5,10b-hexahydro-9-methylpyrrolo[2,3-a]carbazole
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride; pyridine / ethanol
2: 68 percent / p-toluenesulfonic acid / acetonitrile / 6 h / Heating |
|
- 31
-
[ 3449-50-1 ]
-
3,4-dihydro-8-methyl-2-phenyloxeteno[2,3-a]carbazole
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 80 percent / KOH / ethanol / 6 h / 20 °C
2: 80 percent / benzene / 36 h / Irradiation |
|
- 32
-
[ 3449-50-1 ]
-
9-Methyl-1,10-dihydro-1,2,10-triaza-cyclopenta[a]fluorene
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 78 percent / Heating
2: 78 percent / NH2NH2*H2O / ethanol / 5 h / Heating |
|
- 33
-
[ 3449-50-1 ]
-
10-Methyl-3H-pyrazino[3,2,1-jk]carbazole
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: 60 percent / methanol / 1 h / Heating
2: 92 percent / sodium borohydride / methanol / 2 h / Ambient temperature
3: 44 percent / NH4Cl / diphenyl ether / 2 h / Heating |
|
- 34
-
[ 3449-50-1 ]
-
2-(8-Methyl-2,3,4,9-tetrahydro-1H-carbazol-1-ylamino)-ethanol
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 60 percent / methanol / 1 h / Heating
2: 92 percent / sodium borohydride / methanol / 2 h / Ambient temperature |
|
- 35
-
[ 3449-50-1 ]
-
[ 141-78-6 ]
-
2-acetyl-8-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one
[ No CAS ]
-
[ 141-97-9 ]
-
[ 836612-58-9 ]
| Yield | Reaction Conditions | Operation in experiment |
| 1: 56%
2: 10% |
With potassium hydride; sodium hydride In benzene for 2h; Heating; |
|
- 36
-
[ 3449-50-1 ]
-
[ 124-41-4 ]
-
[ 95-92-1 ]
-
[ 934342-66-2 ]
| Yield | Reaction Conditions | Operation in experiment |
| 77% |
In methanol at 0℃; |
|
- 37
-
[ 635-26-7 ]
-
[ 6946-05-0 ]
-
[ 3449-50-1 ]
- 38
-
[ 3449-50-1 ]
-
[ 120-14-9 ]
-
[ 1161434-64-5 ]
| Yield | Reaction Conditions | Operation in experiment |
| 94% |
With potassium hydroxide In ethanol at 20℃; for 24h; |
|
- 39
-
[ 3449-50-1 ]
-
[ 91-56-5 ]
-
[ 1260252-96-7 ]
| Yield | Reaction Conditions | Operation in experiment |
| 85% |
Stage #1: 8-methyl-2,3,4,9-tetrahydro-carbazol-1-one; indole-2,3-dione With sodium hydroxide In ethanol; water for 24h; Reflux;
Stage #2: With hydrogenchloride In water Cooling with ice; |
|
- 40
-
[ 3449-50-1 ]
-
[ 118-92-3 ]
-
[ 1260252-91-2 ]
| Yield | Reaction Conditions | Operation in experiment |
| 45% |
Stage #1: 8-methyl-2,3,4,9-tetrahydro-carbazol-1-one; anthranilic acid With trichlorophosphate at 140℃; for 48h;
Stage #2: With sodium hydroxide In water Cooling with ice; |
|
- 41
-
[ 98-01-1 ]
-
[ 3449-50-1 ]
-
[ 1279703-37-5 ]
| Yield | Reaction Conditions | Operation in experiment |
| 90% |
With potassium hydroxide In ethanol at 20℃; for 6h; |
|
- 42
-
[ 3449-50-1 ]
-
[ 1279703-41-1 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: potassium hydroxide / ethanol / 6 h / 20 °C
2: hydrazine hydrate / ethanol / 6 h / Reflux |
|
- 43
-
[ 3449-50-1 ]
-
[ 1279703-46-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: potassium hydroxide / ethanol / 6 h / 20 °C
2: pyridine; hydroxylamine hydrochloride / 8 h / 130 °C |
|
- 44
-
[ 3449-50-1 ]
-
[ 1279703-61-5 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: potassium hydroxide / ethanol / 6 h / 20 °C
2: sodium hydride / benzene / 24 h / Reflux |
|
- 45
-
[ 3449-50-1 ]
-
[ 1343478-08-9 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: palladium on activated charcoal
2: potassium carbonate / acetone / 3 h / Reflux |
|
- 46
-
[ 3449-50-1 ]
-
[ 1343478-12-5 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: palladium on activated charcoal
2: potassium carbonate / acetone / 3 h / Reflux
3: tetrabutylammomium bromide; palladium diacetate; caesium carbonate / N,N-dimethyl-formamide / 2 h / 110 °C / Inert atmosphere |
|
- 47
-
[ 3449-50-1 ]
-
[ 3433-80-5 ]
-
[ 1343477-99-5 ]
| Yield | Reaction Conditions | Operation in experiment |
| 90% |
With potassium hydroxide In acetone for 3h; Cooling with ice; |
22 General procedure for the synthesis of 9-(2-bromobenzyl)-2,3,4,9-tetrahydro-1H-carbazol-1-one (3):
General procedure: To a solution of respective 2,3,4,9-tetrahydro-1H-carbazol-1-one (1, 1 mmol) and acetone (15 mL), powdered KOH was added in ice cold condition. After few minutes 2-bromobenzylbromide (1 mmol) was added to the solution with vigorous stirring and the reaction mixture was stirred for 3 h. Benzene (75 mL) was added to the reaction mixture and insoluble materials were removed by filtration. The benzene solution was washed with saturated NaCl solution and dried over sodium sulfate. Then, the solvent is evaporated to get the respective 9-(2-bromobenzyl)-2,3,4,9-tetrahydro-1H-carbazol-1-one (3). |
- 48
-
[ 3449-50-1 ]
-
[ 719-59-5 ]
-
[ 1220889-02-0 ]
| Yield | Reaction Conditions | Operation in experiment |
| 85% |
With sulfuric acid; tin(IV) oxide at 20℃; for 0.5h; |
|
| 82% |
With acetic acid |
|
Reference：
[1]Location in patent: experimental part
Roopan, Selvaraj Mohana; Khan, Fazlur Rahman Nawaz
[Medicinal Chemistry Research, 2011, vol. 20, # 6, p. 732 - 737]
[2]Sridharan, Makuteswaran; Prasad, K.J. Rajendra; Madhumitha; Al-Dhabi, Naif Abdullah; Arasu, Mariadhas Valan
[Journal of Photochemistry and Photobiology B: Biology, 2016, vol. 162, p. 641 - 645]
- 49
-
[ 3449-50-1 ]
-
[ 1576-35-8 ]
-
[ 1451422-92-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 90% |
In methanol for 4h; Reflux; |
|
- 50
-
[ 3449-50-1 ]
-
[ 1122-91-4 ]
-
2-(4'-bromobenzylidene)-8-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 75% |
With potassium hydroxide In ethanol at 20℃; for 24h; |
|
- 51
-
[ 3449-50-1 ]
-
4,5-dihydro-9-methyl-3-(4'-bromophenyl)isoxazolo[3,4-a]carbazole
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: potassium hydroxide / ethanol / 24 h / 20 °C
2: hydroxylamine hydrochloride; pyridine / 8 h / 130 °C |
|
- 52
-
[ 3449-50-1 ]
-
4-(4'-bromophenyl)-2-ethoxy-5,6-dihydro-10-methylpyrido[2,3-a]carbazole-3-carbonitrile
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: potassium hydroxide / ethanol / 24 h / 20 °C
2.1: sodium hydride / ethanol; benzene / Cooling with ice
2.2: 5 h / Reflux |
|
- 53
-
[ 3449-50-1 ]
-
2-amino-4-(4'-bromophenyl)-10-methylpyrimido[4,5-a]carbazole
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: potassium hydroxide / ethanol / 24 h / 20 °C
2: sodium hydride / benzene / 18 h / Reflux |
|
- 54
-
[ 3449-50-1 ]
-
9-methyl-2,4,5,10-tetrahydropyrazolo[3,4-a]carbazole
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: sodium hydride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
1.2: 4 h / 20 °C / Inert atmosphere
2.1: hydrazine hydrate / ethanol / 20 °C |
|
- 55
-
[ 3449-50-1 ]
-
[ 109-94-4 ]
-
2-[1-Hydroxy-meth-(E)-ylidene]-8-methyl-2,3,4,9-tetrahydro-carbazol-1-one
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Stage #1: 8-methyl-2,3,4,9-tetrahydro-carbazol-1-one With sodium hydride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
Stage #2: formic acid ethyl ester In tetrahydrofuran at 20℃; for 4h; Inert atmosphere; |
(Z)-2-(hydroxymethylene)-2,3,4,9-tetrahydro-1H-carbazol-1-one (4)
General procedure: Under N2, to a solution of compound 3 (5mmol) in 40mL of dry THF was added 4eq of NaH at room temperature. The mixture was stirred for 1h before ethyl formate was added. The resulted greensolution was quenched with water 4h later and then washed with CHCl3 twice. The aqueous phase was acidified with conc. HCl to pH = 1 - 2 followed by extraction with CHCl3 (3 × 10mL). The combined organic phase was dried with anhydrous MgSO4, evaporated in vacuo. The crude product was purified by flash chromatography (PE : EA = 5:1) to give a yellow solid in 97% yiled. |
- 56
-
[ 823-45-0 ]
-
[ 3449-50-1 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: hydrogenchloride / water / Cooling with ice
1.2: 1 h / -10 - 0 °C
1.3: 3 h / 0 °C
2.1: sulfuric acid / water; acetonitrile / 4 h / Reflux |
|
- 57
-
[ 108-94-1 ]
-
[ 3449-50-1 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: sodium hydride; ethanol / mineral oil; diethyl ether / 20 °C
2.1: hydrogenchloride / water / Cooling with ice
2.2: 1 h / -10 - 0 °C
2.3: 3 h / 0 °C
3.1: sulfuric acid / water; acetonitrile / 4 h / Reflux |
|
- 58
-
[ 53475-32-4 ]
-
[ 3449-50-1 ]
| Yield | Reaction Conditions | Operation in experiment |
| 55% |
With acetic anhydride; bis-[(trifluoroacetoxy)iodo]benzene at 20℃; for 0.166667h; |
4.3. General procedure for the synthesis of substituted tetrahydro-1H-carbazol-1-one 2
General procedure: To a solution of 2-(substituted phenylamino)cyclohex-2-enone 1 (0.6 mmol) in Ac2O (10 mL) was added a solution of PIFA(0.66 mmol) in Ac2O (2 mL) in a dropwise manner. The reactionmixture was stirred at room temperature for 10 min, monitored byTLC. Then the solution was poured into saturated NaHCO3 solution(50 mL) and NaHCO3 (solid) was added portionwise while themixture was stirred vigorously until no more CO2 emerged. Themixture was extracted with EA (20 mL3), and the combined organiclayerwaswashed by brine (20 mL), dried with NaSO4, filtered,and concentrated under vacuum. Purification of the crude residueby column chromatography using PE and EA as eluent gave compounds 2a-l. |
- 59
-
[ 3449-50-1 ]
-
3-(3',4'-diethoxyphenyl)-9-methyl-4,5-dihydro-10H-isoxazolo[3,4-a]carbazole
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: potassium hydroxide / neat (no solvent) / 0.17 h / 20 °C / Milling; Green chemistry
2: pyridine; hydroxylamine hydrochloride / neat (no solvent) / 0.25 h / 130 °C / Milling; Green chemistry |
|
- 60
-
[ 3449-50-1 ]
-
4-(3',4'-diethoxyphenyl)-2-ethoxy-10-methyl-6,11-dihydro-5H-pyrido[2,3-a]carbazole-3-nitrile
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: potassium hydroxide / neat (no solvent) / 0.17 h / 20 °C / Milling; Green chemistry
2: sodium hydride / neat (no solvent) / 0.25 h / 80 °C / Milling; Green chemistry |
|
- 61
-
[ 3449-50-1 ]
-
[ 2029-94-9 ]
-
2-(3',4'-diethoxybenzylidene)-8-methyl-2,3,4,9-tetrahydrocarbazol-1-one
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 89% |
With potassium hydroxide In neat (no solvent) at 20℃; for 0.166667h; Milling; Green chemistry; |
4 4.1.1. General procedure for the synthesis of 2-(30,40-diethoxybenzylidene)-2,3,4,9-tetrahydro-carbazol-1-ones (3a-c).
General procedure: An equimolar mixture of the-2,3,4,9-tetrahydro-carbazol-1-ones (1, 0.005 mol) and 3,4-diethoxy benzaldehyde, (0.005 mol)was grinded in the presence of KOH for 10 min. The reaction wasmonitored by TLC. The reaction mixture was poured into ice coldwater and neutrralised with 1:1 HCl. The precipated product wasrecrystallised from ethanol to yield the respective 2-(30,40-diethoxy-benzylidene)-2,3,4,9-tetrahydro-carbazol-1-one (3). |
- 62
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[ 98-03-3 ]
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[ 3449-50-1 ]
-
[ 109-77-3 ]
-
2-amino-10-methyl-4-(thiophen-2'-yl)-4,5,6-trihydro-11H-pyrano[2,3-a]carbazole-3-carbonitrile
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 67% |
With piperidine In N,N-dimethyl-formamide at 120℃; for 3h; |
General Procedure for the Synthesis of 2-Amino-4-aryl/heteroaryl-5,6-dihydro-11H-pyrano[2,3-a]carbazol-3-carbonitriles 4-8
General procedure: A mixture of an appropriate 2,3,4,9-tetrahydro-1H-carbazol-1-one (1, 1 mmol), malononitrile (2, 1 mmol), and aromatic/heteroaromatic aldehyde (3, 1 mmol) in DMF (10 mL) was refluxed at 120 °C for 3 h in the presence of piperidine (4 drops). After the completion of the reaction, the excess solvent was evaporated and the solid poured into ice-cold water. The obtained solid was filtered, dried, and purified by column chromatography over silica gel using petroleum ether-ethyl acetate (98:2) to yield the respective product. |
- 63
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[ 3449-50-1 ]
-
[ 100-52-7 ]
-
[ 109-77-3 ]
-
2-amino-10-methyl-4-phenyl-4,5,6-trihydro-11H-pyrano[2,3-a]carbazole-3-carbonitrile
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 82% |
With piperidine In N,N-dimethyl-formamide at 120℃; for 3h; |
General Procedure for the Synthesis of 2-Amino-4-aryl/heteroaryl-5,6-dihydro-11H-pyrano[2,3-a]carbazol-3-carbonitriles 4-8
General procedure: A mixture of an appropriate 2,3,4,9-tetrahydro-1H-carbazol-1-one (1, 1 mmol), malononitrile (2, 1 mmol), and aromatic/heteroaromatic aldehyde (3, 1 mmol) in DMF (10 mL) was refluxed at 120 °C for 3 h in the presence of piperidine (4 drops). After the completion of the reaction, the excess solvent was evaporated and the solid poured into ice-cold water. The obtained solid was filtered, dried, and purified by column chromatography over silica gel using petroleum ether-ethyl acetate (98:2) to yield the respective product. |
- 64
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[ 3449-50-1 ]
-
[ 123-11-5 ]
-
[ 109-77-3 ]
-
2-amino-10-methyl-4-(4'-methoxyphenyl)-4,5,6-trihydro-11H-pyrano[2,3-a]carbazole-3-carbonitrile
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 87% |
With piperidine In N,N-dimethyl-formamide at 120℃; for 3h; |
General Procedure for the Synthesis of 2-Amino-4-aryl/heteroaryl-5,6-dihydro-11H-pyrano[2,3-a]carbazol-3-carbonitriles 4-8
General procedure: A mixture of an appropriate 2,3,4,9-tetrahydro-1H-carbazol-1-one (1, 1 mmol), malononitrile (2, 1 mmol), and aromatic/heteroaromatic aldehyde (3, 1 mmol) in DMF (10 mL) was refluxed at 120 °C for 3 h in the presence of piperidine (4 drops). After the completion of the reaction, the excess solvent was evaporated and the solid poured into ice-cold water. The obtained solid was filtered, dried, and purified by column chromatography over silica gel using petroleum ether-ethyl acetate (98:2) to yield the respective product. |
- 65
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[ 3449-50-1 ]
-
[ 104-87-0 ]
-
[ 109-77-3 ]
-
2-amino-10-methyl-4-(4'-methylphenyl)-4,5,6-trihydro-11H-pyrano[2,3-a]carbazole-3-carbonitrile
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 90% |
With piperidine In N,N-dimethyl-formamide at 120℃; for 3h; |
General Procedure for the Synthesis of 2-Amino-4-aryl/heteroaryl-5,6-dihydro-11H-pyrano[2,3-a]carbazol-3-carbonitriles 4-8
General procedure: A mixture of an appropriate 2,3,4,9-tetrahydro-1H-carbazol-1-one (1, 1 mmol), malononitrile (2, 1 mmol), and aromatic/heteroaromatic aldehyde (3, 1 mmol) in DMF (10 mL) was refluxed at 120 °C for 3 h in the presence of piperidine (4 drops). After the completion of the reaction, the excess solvent was evaporated and the solid poured into ice-cold water. The obtained solid was filtered, dried, and purified by column chromatography over silica gel using petroleum ether-ethyl acetate (98:2) to yield the respective product. |
- 66
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[ 3449-50-1 ]
-
[ 1122-91-4 ]
-
[ 109-77-3 ]
-
2-amino-10-methyl-4-(4'-bromophenyl)-4,5,6-trihydro-11H-pyrano[2,3-a]carbazole-3-carbonitrile
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 71% |
With piperidine In N,N-dimethyl-formamide at 120℃; for 3h; |
General Procedure for the Synthesis of 2-Amino-4-aryl/heteroaryl-5,6-dihydro-11H-pyrano[2,3-a]carbazol-3-carbonitriles 4-8
General procedure: A mixture of an appropriate 2,3,4,9-tetrahydro-1H-carbazol-1-one (1, 1 mmol), malononitrile (2, 1 mmol), and aromatic/heteroaromatic aldehyde (3, 1 mmol) in DMF (10 mL) was refluxed at 120 °C for 3 h in the presence of piperidine (4 drops). After the completion of the reaction, the excess solvent was evaporated and the solid poured into ice-cold water. The obtained solid was filtered, dried, and purified by column chromatography over silica gel using petroleum ether-ethyl acetate (98:2) to yield the respective product. |
- 67
-
[ 3449-50-1 ]
-
4-(3'-bromo-4'-methoxyphenyl)-2-ethoxy-5,6-dihydro-10-methyl-11H-pyrido[2,3-a]carbazole-3-carbonitrile
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: potassium hydroxide / ethanol / 24 h / 20 °C
2: sodium hydride / benzene / 5 h / Cooling with ice; Reflux |
|
- 68
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[ 3449-50-1 ]
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2-amino-4-(3'-bromo-4'-methoxyphenyl)-10-methyl-11H-pyrimido[4,5-a]carbazole
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: potassium hydroxide / ethanol / 24 h / 20 °C
2: sodium hydride / benzene / 18 h / Reflux |
|
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