CN104592088B - The method that laurel acid catalysis prepares 3- amine alkyl-indol - Google Patents
The method that laurel acid catalysis prepares 3- amine alkyl-indol Download PDFInfo
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- CN104592088B CN104592088B CN201510011864.8A CN201510011864A CN104592088B CN 104592088 B CN104592088 B CN 104592088B CN 201510011864 A CN201510011864 A CN 201510011864A CN 104592088 B CN104592088 B CN 104592088B
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- aromatic aldehyde
- indol
- amine alkyl
- indole
- amine
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- 238000000034 method Methods 0.000 title claims abstract description 9
- 235000017858 Laurus nobilis Nutrition 0.000 title description 3
- 235000005212 Terminalia tomentosa Nutrition 0.000 title description 3
- 238000007171 acid catalysis Methods 0.000 title description 2
- 244000125380 Terminalia tomentosa Species 0.000 title 1
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000003934 aromatic aldehydes Chemical class 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 239000005639 Lauric acid Substances 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 150000003335 secondary amines Chemical class 0.000 claims abstract description 5
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims description 10
- 239000012043 crude product Substances 0.000 claims description 8
- 238000004440 column chromatography Methods 0.000 claims description 5
- -1 alkyl indole Chemical compound 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 8
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 5
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 5
- 239000012153 distilled water Substances 0.000 claims 1
- 150000002475 indoles Chemical class 0.000 abstract description 14
- 238000002360 preparation method Methods 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 239000003960 organic solvent Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000003125 aqueous solvent Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 150000004671 saturated fatty acids Chemical class 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- VTTONGPRPXSUTJ-UHFFFAOYSA-N bufotenin Chemical compound C1=C(O)C=C2C(CCN(C)C)=CNC2=C1 VTTONGPRPXSUTJ-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000003810 ethyl acetate extraction Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- QVDSEJDULKLHCG-UHFFFAOYSA-N psilocybin Chemical compound C1=CC(OP(O)(O)=O)=C2C(CCN(C)C)=CNC2=C1 QVDSEJDULKLHCG-UHFFFAOYSA-N 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
- PYIXHKGTJKCVBJ-UHFFFAOYSA-N Astraciceran Natural products C1OC2=CC(O)=CC=C2CC1C1=CC(OCO2)=C2C=C1OC PYIXHKGTJKCVBJ-UHFFFAOYSA-N 0.000 description 1
- NDVRQFZUJRMKKP-UHFFFAOYSA-N Betavulgarin Natural products O=C1C=2C(OC)=C3OCOC3=CC=2OC=C1C1=CC=CC=C1O NDVRQFZUJRMKKP-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- 241000218195 Lauraceae Species 0.000 description 1
- 244000147568 Laurus nobilis Species 0.000 description 1
- IHPVFYLOGNNZLA-UHFFFAOYSA-N Phytoalexin Natural products COC1=CC=CC=C1C1OC(C=C2C(OCO2)=C2OC)=C2C(=O)C1 IHPVFYLOGNNZLA-UHFFFAOYSA-N 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 229940089536 indocin Drugs 0.000 description 1
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 239000000280 phytoalexin Substances 0.000 description 1
- 150000001857 phytoalexin derivatives Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
The present invention relates to a kind of preparation methods of organic synthesis intermediate 3- amine alkyl-indol.The present invention directlys adopt lauric acid as catalyst, prepares 3- amine alkyl-indol by aromatic aldehyde, indoles and secondary amine one-step method.The present invention has the features such as catalyst is inexpensive without preparation, safety, and reaction condition is mild, easy to operate, and reaction process is avoided using organic solvent, and yield is higher.
Description
Technical field
The present invention relates to a kind of preparation method of indole derivatives more particularly to a kind of use linear saturated fatty acids laurels
Acid is catalyst, the method for preparing 3- amine alkyl-indol by aromatic aldehyde, indoles and secondary amine.
Background technique
Indoles is important pharmaceutical intermediate, and structural unit is present in many important natural prodcuts.Known
In more than 3000 kinds of natural indole derivatives, more than 40 kinds are therapeutic type drugs.Many drugs all contain indoles knot currently on the market
Structure unit, wherein 3- substituted indole derivative occupies certain ratio, such as tryptophan is necessary amino acid and various colors
The biosynthesis precursor of amine, indoles；Psilocybin is that certain toadstools cause unreal ingredient；Bufotenine has anesthetic effect；Brazilian alkali
It is resistant to the phytoalexin of microbial challenge；5- hydroxyl color ammonia is important transmitter substance, and derivative can treat partially
Headache；Indocin is for treating rheumatic arthritis etc..The synthesis of current most of 3- amine alkyl-indol compounds is organic molten
It is carried out in agent, VOCs pollution is generated to environment, does not meet the Economic Development Mode of green low-carbon.
Summary of the invention
The object of the present invention is to provide a kind of without preparation, the inexpensive saturated fatty acid lauric acid of safety as catalyst,
Using aromatic aldehyde, indoles and secondary amine as raw material, one-step method mildly prepares 3- amine alkyl-indol in water method.
Technical solution of the present invention is as follows:
The present invention directlys adopt aromatic aldehyde, indoles and secondary amine and reacts in water, is used as and is urged by saturated fatty acid lauric acid
Agent is stirred to react preparation 3- amine alkyl-indol.The wherein aromatic aldehyde, R are hydrogen, halogen, alkoxy or nitro.This hair
Bright reaction equation is as follows:
The method that the present invention prepares 3- amine alkyl-indol, steps are as follows:
1) aromatic aldehyde, methylphenylamine, catalyst lauric acid and a certain amount of aqueous solvent are added into reaction flask, wherein virtue
Fragrant aldehyde and methylphenylamine molar ratio are 1: 1.0~1.5, and aromatic aldehyde and lauric molar ratio are stirred under the conditions of being 1: 0.2,80 DEG C
Reaction 5-10min is mixed, white opacity thing imine intermediate is obtained, the indoles equal with aromatic aldehyde molal quantity is added later and continues to stir
It mixes reaction certain time, TLC tracking reaction.
2) ethyl acetate extraction is added after reaction and dries organic phase with anhydrous sodium sulfate, obtained slightly after solvent is evaporated off
Product.Crude product petroleum ether and ethyl acetate do after eluant, eluent carries out column chromatography for separation and obtain aubergine solid 3- amine alkyl Yin
Diindyl.
The preferred aromatic aldehyde of the step 1), methylphenylamine and indoles molar ratio are 1: 1.2: 1；
Preferably, step 1) the catalyst lauric acid is 20% relative to the mole percent of aromatic aldehyde.
For the present invention with catalyst without preparation, safety is inexpensive, and the reaction time is short, mild condition, environmental-friendly, operation is simple
Singly, the advantages that yield is higher.
Specific embodiment
The present invention will be further explained with reference to the examples below, but not limited to this.
The synthesis of embodiment 1, N- (3- indyl-phenyl) methyl-N-methyl aniline, structural formula are as follows:
In 25ml round-bottomed flask be added 1.0mmol benzaldehyde, 1.2mmol methylphenylamine, 0.2mmol lauric acid and
2.0ml aqueous solvent, 80 DEG C of whens, are stirred to react 5 minutes, 1.0mmol indoles are added later, continues to be stirred to react 3.5 hours, TLC inspection
Stop reaction after surveying fully reacting.After being cooled to room temperature, ethyl acetate extraction is added and dries organic phase with anhydrous sodium sulfate, adopts
Solvent ethyl acetate, which is removed, with Rotary Evaporators obtains crude product.Crude product ethyl acetate and petroleum ether make eluant, eluent (acetic acid
Ethyl ester: petroleum ether=1: 4), using gradient elution, after carrying out column chromatography for separation (200-300 mesh silica gel), obtaining purity is 99%
Red brown solid N- (3- indyl-phenyl) methyl-N-methyl aniline 244.0mg, separation yield is 78.1%, and fusing point is
128-130℃。
The identification of N- (3- indyl-phenyl) methyl-N-methyl aniline:
Infrared spectrogram IR (KBr) v:735,1453,1509,1612,2927,3363,3409cm-1.
Nuclear magnetic resonance data:1H NMR (500MHz, CDCl3): δ 2.77 (s, 3H), 5.54 (s, 1H), 6.52 (d, J=
8.0Hz, 3H), 6.69-6.83 (m, 3H), 7.04 (d, J=10.0Hz, 2H), 7.13-7.35 (m, 6H), 7.57 (s, 1H),
7.88 (s, 1H) ppm.13C NMR (125MHz, CDCl3): δ 30.6,47.8,111.0,112.4,119.3,119.8,122.1,
124.0,126.8,128.1,128.9,129.5,130.2,133.1,136.6,144.9,147.9.
Product is identified consistent with document report.
The synthesis of embodiment 2, N- (3- indyl-(4- nitrobenzophenone)) methyl-N-methyl aniline, structural formula are as follows:
1.0mmol paranitrobenzaldehyde, 1.2mmol methylphenylamine, the 0.2mmol month are added in 25ml round-bottomed flask
Cinnamic acid and 2.0ml aqueous solvent, 80 DEG C of whens, are stirred to react 5 minutes, and 1.0mmol indoles is added later, continue to be stirred to react 2.5 small
When, TLC stops reaction after detecting fully reacting.After being cooled to room temperature, the extraction of addition ethyl acetate is simultaneously dry with anhydrous sodium sulfate
Organic phase removes solvent ethyl acetate using Rotary Evaporators and obtains crude product.Crude product is washed with ethyl acetate and petroleum ether
De- agent (ethyl acetate: petroleum ether=1: 4), is obtained after carrying out column chromatography for separation (200-300 mesh silica gel) using gradient elution
Red brown solid N- (3- indyl-(4- nitrobenzophenone)) methyl-N-methyl aniline 286.6mg that purity is 99%, separation produce
Rate is 80.2%, and fusing point is 60-62 DEG C.
The identification of N- (3- indyl-(4- nitrobenzophenone)) methyl-N-methyl aniline:
Infrared spectrogram IR (KBr) v:739,1347,1456,1521,1608,2935,3411cm-1.
Nuclear magnetic resonance data:1H NMR (500MHz, CDCl3): δ 2.85 (s, 3H), 5.57 (s, 1H), 6.49-6.54 (m,
3H), 6.89-7.00 (m, 3H), 7.12-7.19 (m, 2H), 7.28-7.53 (m, 4H), 8.01 (s, 1H), 8.13 (d, J=
10.0Hz, 2H)；13C NMR (125MHz, CDCl3): δ 31.1,47.6,111.0,112.3,119.6,120.2,122.3,
123.5,124.0,126.7,129.3,130.8,136.7,146.2,147.9,152.2.
Product is identified consistent with document report.
Embodiment 3, N- (synthesis of 3- indyl-(4- methoxyphenyl) methyl-N-methyl aniline, structural formula are as follows:
1.0mmol P-methoxybenzal-dehyde, 1.2mmol methylphenylamine, 0.2mmol are added in 25ml round-bottomed flask
Lauric acid and 2.0ml aqueous solvent, 80 DEG C of whens, are stirred to react 5 minutes, and 1.0mmol indoles is added later, continue to be stirred to react 4.5 small
When, TLC stops reaction after detecting fully reacting.After being cooled to room temperature, the extraction of addition ethyl acetate is simultaneously dry with anhydrous sodium sulfate
Organic phase removes solvent ethyl acetate using Rotary Evaporators and obtains crude product.Crude product is washed with ethyl acetate and petroleum ether
De- agent (ethyl acetate: petroleum ether=1: 4), is obtained after carrying out column chromatography for separation (200-300 mesh silica gel) using gradient elution
Red brown solid N- (3- indyl-(4- methoxyphenyl) methyl-N-methyl aniline 234.5mg, the separation that purity is 98.5%
Yield is 68.5%, and fusing point is 142-143 DEG C.
N- (identification of 3- indyl-(4- methoxyphenyl) methyl-N-methyl aniline:
Infrared spectrogram IR (KBr) v:IR (KBr): 745,1026,1181,1451,1510,1616,2925,3041,
3403cm-1.
Nuclear magnetic resonance data:1H NMR (500MHz, CDCl3): δ 2.79 (s, 3H), 3.77 (s, 3H), 5.53 (s, 1H),
6.50-6.57 (m, 2H), 6.82-6.89 (m, 3H), 6.98-7.07 (m, 3H), 7.13 (d, J=10.0,3H), 7.23-7.39
(m, 3H), 7.87 (s, 1H)；13C NMR (125MHz, CDCl3): δ 30.8,47.7,55.1,111.2,112.5,113.6,
119.7,119.8,121.8,123.5,123.7,127.0,129.6,129.7,133.1,136.8,147.5,157.6.
Product is identified consistent with document report.
According to the disclosure of the present invention, those skilled in the art can be to greatest extent using the present invention.Therefore,
Above-mentioned preferred embodiment is merely illustrative of, rather than is limited the scope of the invention in any way.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201510011864.8A CN104592088B (en) | 2015-01-05 | 2015-01-05 | The method that laurel acid catalysis prepares 3- amine alkyl-indol |
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| CN201510011864.8A CN104592088B (en) | 2015-01-05 | 2015-01-05 | The method that laurel acid catalysis prepares 3- amine alkyl-indol |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020198252A1 (en) * | 2001-05-24 | 2002-12-26 | Joseph Payack | Process for the preparation of alkylamine substituted indoles |
| CN102015642A (en) * | 2008-02-19 | 2011-04-13 | 赛诺菲-安万特 | Novel 3-aminoalkyl-1,3-dihydro-2H-indol-2-one derivatives, processes for their preparation and their therapeutic use |
| CN103342675A (en) * | 2013-05-17 | 2013-10-09 | 安徽工业大学 | Preparation method of diindolylmethane derivative through catalysis |
-
2015
- 2015-01-05 CN CN201510011864.8A patent/CN104592088B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020198252A1 (en) * | 2001-05-24 | 2002-12-26 | Joseph Payack | Process for the preparation of alkylamine substituted indoles |
| CN102015642A (en) * | 2008-02-19 | 2011-04-13 | 赛诺菲-安万特 | Novel 3-aminoalkyl-1,3-dihydro-2H-indol-2-one derivatives, processes for their preparation and their therapeutic use |
| CN103342675A (en) * | 2013-05-17 | 2013-10-09 | 安徽工业大学 | Preparation method of diindolylmethane derivative through catalysis |
Non-Patent Citations (5)
| Title |
|---|
| Carboxylic Acid Catalyzed Three-Component Aza-Friedel-Crafts Reactions in Water for the Synthesis of 3-Substituted Indoles;Seiji Shirakawa，等;《Org. Lett.》;20060923;第8卷(第21期);4939-4942 |
| Catalyst-free, ethylene glycol promoted one-pot three component synthesis of 3-amino alkylated indoles via Mannich-type reaction;U. Chinna Rajesh，等;《Tetrahedron Letters》;20140403(第55期);第2977–2981页 |
| L-Proline catalysed multicomponent synthesis of 3-amino alkylated indoles via a Mannich-type reaction under solvent-free conditions;Atul Kumar，等;《Green Chem.》;20121231;第14卷;290-295 |
| One-Pot Synthesis of 3-[(N-Alkylanilino)(aryl)methyl]indoles via a Transition Metal Assisted Three-Component Condensation at Room Temperature;Goutam Brahmachari，等;《Journal of Heterocyclic Chemistry》;20140418;E140-E145 |
| One-pot synthesis of 3-substituted indole derivatives using moisture stable, reusable, and task specific ionic liquid catalysts;Ravindran, Anaswara，等;《 Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry 》;20130131;第52B卷(第1期);129-135 |
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| CN104592088A (en) | 2015-05-06 |
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