6747-15-5

Usage

Uses

Used in Organic Synthesis:
AMINO-(1H-INDOL-3-YL)-ACETIC ACID is used as a synthetic building block for the development of various organic compounds. Its unique structure allows it to be a versatile component in the synthesis of a wide range of molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, AMINO-(1H-INDOL-3-YL)-ACETIC ACID is used as an intermediate in the synthesis of various drugs. Its ability to form a wide range of chemical bonds makes it a valuable component in the development of new medications with specific therapeutic properties.
Used in Agrochemical Industry:
AMINO-(1H-INDOL-3-YL)-ACETIC ACID is also utilized in the agrochemical industry for the synthesis of various agrochemical products, such as pesticides and herbicides. Its unique chemical properties enable the creation of effective and targeted compounds for agricultural applications.
Used in Research and Development:
In the field of research and development, AMINO-(1H-INDOL-3-YL)-ACETIC ACID serves as a valuable compound for studying the properties and behavior of organic molecules. Its use in various chemical reactions and processes helps researchers gain a deeper understanding of organic chemistry and develop new methodologies for synthesizing complex molecules.

InChI:InChI=1/C10H10N2O2/c11-9(10(13)14)7-5-12-8-4-2-1-3-6(7)8/h1-5,9,12H,11H2,(H,13,14)

Upstream product

• 120-72-9 indole 
• 58237-94-8 N-Boc-indol-3-ylglycine 
• 1245652-53-2 C₁₀H₈N₂O₃ 
• 22980-09-2 indolyl-3-glyoxylyl chloride 
• 120133-83-7 ethyl α-<(diphenylmethylene)amino>-(+/-)-3-indolacetate 
• 110317-47-0 (Z)-2-(3-Indolyl)-2-(hydroxyimino)essigsaeure-methylester 
• 18372-22-0 2-(3-indolyl)oxoacetic acid methyl ester 
• 1477-49-2 3-indolylglyoxylic acid 
• 110317-55-0 (E)-2-(3-Indolyl)-2-(hydroxyimino)essigsaeure-methylester 
• 91566-74-4 α-aminoindole-3-acetic acid ethyl ester 
• 110317-48-1 methyl 2-amino-2-(1H-indol-3-yl)acetate 

Downstream Products

• 294888-41-8 (+/-)-N-benzyloxycarbonyl-3-indoleglycinate 
• 470670-73-6 2,5-dioxo-4-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-oxazolidine-3-carboxylic acid benzyl ester 
• 294888-39-4 (+/-)-methyl-N-benzyloxycarbonyl-3-indoleglycinate 
• 470670-87-2 (+/-)-N-benzyloxycarbonyl-1-tosyl-3-indoleglycine 
• 470670-88-3 (+/-)-methyl-N-benzyloxycarbonyl-1-tosyl-3-indoleglycinate 

Relevant academic research and scientific papers

Novel synthesis method of indole glycinate

The invention relates to a novel synthesis method of indole glycinate. A substituted indole glycinate derivative 3 is obtained after indole 1, acylamino malonate 2 and an oxidant as raw materials are heated to 60-100 DEG C in an organic solvent under the protection of nitrogen and are subjected to a cross dehydrogenation coupling reaction, an obtained product is treated and subjected to hydrolysis and decarboxylation under the alkaline condition, a product 4 is obtained and subjected to hydrolysis deprotection under the alkaline condition, and a final indole glycinate product 5 is obtained through acidification. Indole 1, acylamino malonate 2 and the oxidant are taken as the raw materials, the raw materials are cheap and easy to obtain, a substrate range is wide, the compatibility of a functional group is good, and final indole glycinate can be obtained in a higher yield from various substituted indole and acylamino malonate. The method has multiple advantages that the synthesis route is short, the reaction raw materials are low in toxicity, separation and purification are convenient and the like, and has great practical application value in synthesis of the compounds.

CATALYST COMPOUNDS

The present invention relates to an iridium-based catalyst compound for hydrogenating reducible moieties, especially imines and iminiums, the catalyst compounds being defined by the formulas: where ring B is either itself polycyclic, or ring B together with R is polycyclic. The catalysts of the invention are particularly effective in reductive amination procedures 10 which involve the in situ generation of the imine or iminium under reductive hydrogenative conditions.

Primary amines by transfer hydrogenative reductive amination of ketones by using cyclometalated IrIII catalysts

Cyclometalated iridium complexes are found to be versatile catalysts for the direct reductive amination (DRA) of carbonyls to give primary amines under transfer-hydrogenation conditions with ammonium formate as both the nitrogen and hydrogen source. These complexes are easy to synthesise and their ligands can be easily tuned. The activity and chemoselectivity of the catalyst towards primary amines is excellent, with a substrate to catalyst ratio (S/C) of 1000 being feasible. Both aromatic and aliphatic primary amines were obtained in high yields. Moreover, a first example of homogeneously catalysed transfer-hydrogenative DRA has been realised for β-keto ethers, leading to the corresponding β-amino ethers. In addition, non-natural α-amino acids could also be obtained in excellent yields with this method. Reduce the work! A broad range of ketones have been successfully aminated to afford primary amines under transfer-hydrogenation conditions by using ammonium formate as the amine source and 0.1 mol % of a cyclometalated IrIII catalyst (see scheme). Copyright

Dissecting metabolic puzzles through isotope feeding: A novel amino acid in the biosynthetic pathway of the cruciferous phytoalexins rapalexin A and isocyalexin A

Understanding defence pathways of plants is crucial to develop disease-resistant agronomic crops, an important element of sustainable agriculture. For this reason, natural plant defenses such as phytoalexins, involved in protecting plants against microbial pathogens, have enormous biotechnological appeal. Crucifers are economically important plants, with worldwide impact as oilseeds, vegetables of great dietetic value and even nutraceuticals. Notably, the intermediates involved in the biosynthetic pathways of unique cruciferous phytoalexins such as rapalexin A and isocyalexin A remain unknown. Toward this end, using numerous perdeuterated compounds, we have established the potential precursors of these unique phytoalexins and propose for the first time their detailed biosynthetic pathway. This pathway involves a variety of intermediates and a novel amino acid as the central piece of this complex puzzle. This work has set the stage for the discovery of enzymes and genes of the biosynthetic pathway of cruciferous phytoalexins of unique scaffolds.

CATALYST COMPOUNDS

The present invention relates to an iridium-based catalyst compound for hydrogenating reducible moieties, especially imines and iminiums, the catalyst compounds being defined by the formulas: where ring B is either itself polycyclic, or ring B together with R is polycyclic. The catalysts of the invention are particularly effective in reductive amination procedures 10 which involve the in situ generation of the imine or iminium under reductive hydrogenative conditions.

Catalytic Leuckart-Wallach-type reductive amination of ketones

A Cp*Rh(III) complex catalyzes reductive amination of ketones using HCOONH4 at 50-70°C to give the corresponding primary amines in high yields. The reaction is clean and operationally simple and proceeds at a lower temperature and with higher chemoselectivity than the original Leuckart-Wallach reaction. The new method has been applied to the synthesis of α-amino acids directly from α-keto acids.

Alboinon, an oxadiazinone alkaloid from the ascidian Dendrodoa grossularia

The ascidian Dendrodoa grossularia, collected in the Baltic Sea, contains the new 1,3,5-oxadiazin-2-one alkaloid alboinon (1).

α-amino-indole-3-acetic acids useful as anti-diabetic, anti-obesity and anti-atherosclerotic agents

Provided are novel α-aminoindole-3-acetic acid derivatives having the formula STR1 wherein R through R9 are as defined in the specification, and pharmacologically acceptable salts of compounds wherein R9 is not OM, which are useful as anti-diabetic, anti-obesity and anti-atherosclerotic agents.

THE SYNTHESIS OF AMINO ACIDS BY REACTION OF AN ELECTROPHILIC GLYCINE CATION EQUIVALENT WITH NEUTRAL CARBON NUCLEOPHILES

Seven neutral carbon nucleophiles (active aromatics, allylsilanes and a silyl enol ether) were reacted with the glycine cation equivalent 12 in the presence of TiCl4 to yield α-substituted amino acid derivatives in moderate yield (1-61.5 mmolar scale).Deprotection of the Schiff base ester products led to the corresponding amino acids.

Hexahydropyrroloindoles - Attempts to Synthesize 2-Indolyl Thioethers

The N-tryptamine derivatives 9, 11, 12, and 19 with the functional groups CN, CONH2, CO2H, and CO2Me, respectively, in the α position to the indole ring have been synthesized.Sensitized photooxiation of 9, 12, 19, N-Boc--tryptophan (21), and N-Boc-tryptamine (22) affords the hexahydropyrroloindoles 23-27, in the case of 11 the ring closure occurs at the amine nitrogen to give the ketone 28, N-Boc-homotryptamine (31) yields the hexahydropyridoindole 32, whereas no azetidine formation from 2-(3-indolyl)glycine (36) is observed.The oxi mes 34a and 34 b, intermediates in the synthesis of 36, have been separated chromatographically and characterized NMR spectroscopically as E and Z-isomers, respectively.- Attempts to introduce with cysteine derivatives a thioether group in position 2 of the compounds described above, failed. 21, 22, 26, 27, and N-Boc-2-(3-indolyl)propylamine (43), bearing a methyl group in the α position to the indole ring, and its photooxidation product 44 show only thin-layer chromatographically detectable thioether formation.