2380-94-1Relevant articles and documents
A PHOTOCHEMICAL SYNTHESIS OF 4-HYDROXYINDOLE
Kaneko, Chikara,Okuda, Wakako,Karasawa, Yoshio,Somei, Masanori
, p. 547 - 550 (1980)
1-Alkoxycarbonyl-4-hydroxyindoles were prepared in ca. 25percent yields from 5-(alkoxycarbonylamino)isoquinoline 2-oxides by irradiation in an aprotic solvent, followed by an acid treatment under solvolytic conditions. 1-benzyloxycarbonyl-4-hydroxyindole was then converted to the title compound by catalytic hydrogenation.
Synthetic method of 4-hydroxyindole
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Paragraph 0039; 0077-0083, (2021/03/30)
The invention belongs to the technical field of organic synthesis, and particularly relates to a synthetic method of 4-hydroxyindole. Aiming at the problems existing in industrial production of 4-hydroxyindole in the prior art, the technical scheme of the invention is as follows: the method comprises the following steps: (1) protecting hydroxyl in a compound 3 by using a protective group to obtaina compound 4; (2) reacting the compound 4 with N, N-dimethylformamide dimethyl acetal to obtain a compound 5; (3) mixing the compound 5 with NH2NH2.H2O and MeOH, and carrying out a reaction to obtaina compound 6; and (4) removing the protective group of the compound 6 to obtain 4-hydroxyindole. According to the method for synthesizing 4-hydroxyindole, the cost of starting materials is low, the reaction conditions in the synthesis process are mild, operation is convenient, aftertreatment is simple, and the yield is high.
Synthesis of Substituted Anilines from Cyclohexanones Using Pd/C-Ethylene System and Its Application to Indole Synthesis
Maeda, Katsumi,Matsubara, Ryosuke,Hayashi, Masahiko
supporting information, p. 1530 - 1534 (2021/03/08)
The synthesis of anilines and indoles from cyclohexanones using a Pd/C-ethylene system is reported. A simple combination of NH4OAc and K2CO3 under nonaerobic conditions was found to be the most suitable to perform this reaction. Hydrogen transfer between cyclohexanone and ethylene generates the desired products. The reaction tolerates a variety of substitutions on the starting cyclohexanones.
Method for synthesizing 4 -hydroxyindole
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Paragraph 0025; 0028-0029; 0030; 0033-0034, (2021/09/01)
The invention discloses a novel method for synthesizing 4 -hydroxyindole, and belongs to the field of medical intermediate synthesis. With 1, 3 - Cyclohexanedione reacts with 2 - aminoethanol to produce a corresponding enamine compound which is then converted to 4 - hydroxyindole in the presence of a supported or framework-type metal catalyst. The synthesis route is short in step, high-temperature reaction of the pressure vessel is avoided, 4 - hydroxyl indole synthesis efficiency and safety are improved. 2 - Aminoethanol is adopted as the synthetic raw material, the use of higher 2 - chloroacetaldehyde is avoided, the reaction by-product with 1 and 3 - cyclohexanedione is water, and the reaction by-product of the generated enamine under the action of the catalyst is H. 2 , 4 - Hydroxyl indole production cost is reduced.
4-hydroxyindole preparation method suitable for industrial production
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Paragraph 0071; 0072, (2019/11/19)
The invention relates to the technical field of organic synthesis, in particular to a preparation method of a medical intermediate 4-hydroxyindole. The method includes: taking 1, 5, 6, 7-tetrahydro-4H-indole-4-one as the raw material, carrying out nucleophilic substitution reaction under the action of alkali to obtain an amino protection product (I), reacting the compound (I) with a halogenation reagent to obtain alpha-halogenated ketone (II), subjecting the compound (II) to elimination reaction under the action of alkali to remove HX so as to obtain a 4-hydroxyindole derivative (III), and finally conducting hydrolysis deprotection on the compound (III) to obtain 4-hydroxyindole (IV). The invention provides a simple industrial production route for 4-hydroxyindole, and the method has the advantages of simple reaction operation, avoidance of high temperature, high pressure and catalytic reaction, and low cost.
Synthesis and structure eassessment of psammopemmin a
Lebar, Matthew D.,Baker, Bill J.
experimental part, p. 862 - 866 (2011/08/09)
We have isolated meridianins A, B, C, and E from the Antarctic tunicate Synoicum sp. In the process of verifying the structure of these compounds it was noted that the physical data reported for meridianins bore a striking resemblance to that of psammopemmins. The psammopemmins are alkaloids bearing similar structures to the meridianins, but reported from the Antarctic sponge Psammopemma sp. To verify the structure originally proposed for psammopemmin A, the compound was synthesized. By comparing the 1H and 13C NMR data of reported and synthetic psammopemmin A with that of meridianin A, we infer that the correct structure of psammopemmin A isolated from Psammopemma sp. is actually that of meridianin A.
Synthesis and adrenolytic activity of 1-(1H-indol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol and its enantiomers. Part 1
Groszek, Grazyna,Bednarski, Marek,Dybala, Malgorzata,Filipek, Barbara
scheme or table, p. 809 - 817 (2009/09/05)
The synthesis of (2RS)-1-(1H-indol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol ((RS)-9) and its enantiomers has been described and tested for electrocardiographic, antiarrhythmic, hypotensive and spasmolytic activities as well as for α1-, α2- and β1-adrenoceptors' binding affinities. All compounds significantly decrease systolic and diastolic blood pressure, and possess antiarrhythmic activity and affinity to α1-, α2- and β1-adrenoceptors. The results suggest that the antiarrhythmic and hypotensive effects of these compounds are related to their adrenolytic but not spasmolytic properties.
Highly chemoselective reduction using a Rh/C-Fe(OAc)2 system: Practical synthesis of functionalized indoles
Akao, Atsushi,Sato, Kimihiko,Nonoyama, Nobuaki,Mase, Toshiaki,Yasuda, Nobuyoshi
, p. 969 - 972 (2007/10/03)
Here, we report a highly effective and chemoselective method of preparing substituted indoles from (E)-2-nitropyrrolidinostyrenes via hydrogenation in the presence of a rhodium catalyst doped by additives such as Ni(NO 3)2·6H2O, Fe(OAc)2 or Co(acac)3. These hydrogenation conditions may also be applied to other substrates. Aromatic nitro compounds and olefins can be selectively reduced in the presence of aromatic benzyl ethers, aromatic halides and aromatic aldehydes.
PROCESS FOR PRODUCING INDOLOPYRROLOCARBAZOLE DERIVATIVE
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Page/Page column 38, (2010/02/11)
The present invention provides a process for industrially advantageously producing a compound represented by the formula (I): or a pharmaceutically acceptable salt thereof, which is useful as an anticancer agent, and also provides a catalyst used for hydrogenation reaction in the process.
Process for the preparation of indole compounds
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, (2008/06/13)
The present invention relates to a novel process for the preparation of a monohydroxyindole or dihydroxyindole compound by a single step of placing in contact, in a solvent medium, at least one hydrolase with at least one indole compound bearing one or two radicals connected by an ester function to the benzene ring.
