Category: indole-building-block

On May 30, 2002, Dugar, Sundeep; Luedtke, Gregory; Tan, Xuefei published a patent.Application In Synthesis of 6-Chloro-1H-indole-5-carboxylic acid The title of the patent was Preparation of piperidinylcarbonyl- and piperazinylcarbonylindolylglyoxylates and -amides as inhibitors of p38-α kinase. And the patent contained the following:

[Title compounds I; dotted line = optional double bond; B = WiCOXjY; Y = COR2, isostere thereof; R2 = H, noninterfering substituent; W, X = spacer of 2-6 Å; i, j = 0, 1; R3 = noninterfering substituent; n = 0-3; Z3 = NR7, O; R7 = H, noninterfering substituent; 1 Z2 = C, CR8A, the other = CR1, C(R1)2, NR6, N; R1, R6, R8 = H, noninterfering substituent; A = Q1; Z1 = CR5, N; R5 = H, noninterfering substituent; p, q = 0-2; p+q = 0-3; Ar = aryl group substituted with 0-5 noninterfering substituents, wherein two noninterfering substituents can form a fused ring; R4 = noninterfering substituent; m is 0-4; L1, L2 = linker; the distance between the atom of Ar linked to L2 and the center of the Z2-containing ring = 4.5-24Å], were prepared as inhibitors of p38-α kinase (no data). Thus, title compound (II) was prepared in several steps starting from 4-nitrophenylglyoxylic acid. The experimental process involved the reaction of 6-Chloro-1H-indole-5-carboxylic acid(cas: 256935-86-1).Application In Synthesis of 6-Chloro-1H-indole-5-carboxylic acid

The Article related to indolylglyoxylate piperidinylcarbonyl preparation p38 kinase inhibitor, piperazinylcarbonylindolylglyoxamide preparation p38 kinase inhibitor, proinflammation response treatment indolylglyoxamide preparation and other aspects.Application In Synthesis of 6-Chloro-1H-indole-5-carboxylic acid

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Zhang, Wenzheng; Xu, Guangyang; Qiu, Lin; Sun, Jiangtao published an article in 2018, the title of the article was Gold-catalyzed C5-alkylation of indolines and sequential oxidative aromatization: access to C5-functionalized indoles.Recommanded Product: 52537-00-5 And the article contains the following content:

A novel protocol for the synthesis of C5-alkylated indole derivatives I (R = C(O)OCH3, naphthalen-2-yl, thiophen-2-yl, etc.; R1 = CH3, CH2C6H5, pyrimidin-2-yl, etc.; R2 = H, 3-CH3, 2-CH3; R3 = 4-CN, 6-Cl, 7-CH3O, etc.) via a gold-catalyzed reaction of indolines II with diazo compounds RC(=N2)C(O)OCH3 and subsequent oxidative aromatization has been developed. C-H bond functionalization selectively occurs at the C5-position of indolines III without a directing group. The exptl. operation is simple and the whole process can be manipulated in one-pot. The experimental process involved the reaction of 6-Chloro-2,3-dihydro-1H-indole(cas: 52537-00-5).Recommanded Product: 52537-00-5

The Article related to alkyl indoline preparation regioselective, diazo compound indoline alkylation gold catalyst, indole alkyl preparation regioselective, indoline diazo compound alkylation gold catalyst oxidative aromatization and other aspects.Recommanded Product: 52537-00-5

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On March 28, 2011, Masuda, Kohei; Ohmura, Toshimichi; Suginome, Michinori published an article.Safety of 1,5-Dimethyl-1H-indole-2-carbaldehyde The title of the article was 2-Vinylindoles As the Four-Atom Component in a Catalytic [4+1] Cycloaddition with a Silylene-Palladium Species Generated from (Aminosilyl)boronic Ester. And the article contained the following:

The palladium-catalyzed silylene transfer to 2-alkenylindoles from a silylboronic ester bearing a diethylamino group on the silicon atom takes place efficiently, resulting in the formation of a 1-sila-3-cyclopentene ring fused with the indole ring. Further silylene transfer proceeds in the reaction of 2-(1-alkenyl)indoles, giving bissilylated tricyclic indoles in high yields. The experimental process involved the reaction of 1,5-Dimethyl-1H-indole-2-carbaldehyde(cas: 883526-76-9).Safety of 1,5-Dimethyl-1H-indole-2-carbaldehyde

The Article related to vinylindole preparation palladium phosphine catalyzed bissilylative cyclization, indolosilacyclopentene preparation crystal mol structure, catalysis cycloaddition silylene palladium aminosilylboronic ester and other aspects.Safety of 1,5-Dimethyl-1H-indole-2-carbaldehyde

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On July 31, 1997, Nilsson, Kurt G.I.; Pan, Hefeng; Larsson-Lorek, Ulla published an article.Recommanded Product: 130539-43-4 The title of the article was Synthesis of modified carbohydrates with glycosidases: stereo- and regiospecific syntheses of lactosamine derivatives and related compounds. And the article contained the following:

Different lactosamine derivatives, modified in the 2-N- and anomeric positions and suitable as intermediates for synthesis of Lewis-x and related compounds, were prepared with high specificity on a multigram scale directly from lactose, employing different D-glucosamine derivatives as acceptors and the abundant β-D-galactosidase from Bullera singularis as catalyst. Thus, Me O-β-D-galactopyranosyl-(1→4)-2-azido-2-deoxy-β-D-glucopyranoside, Et O-β-D-galactopyranosyl-(1→4)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside and Et O-β-D-galactopyranosyl-(1→4)-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside were formed in 20-40% yield as calculated based on added acceptor. The 2-phthalimido derivative was isolated in crystalline form without chromatog. (extraction/crystallization procedure). The trisaccharide derivative Et O-β-D-galactopyranosyl-(1→4)-O-β-D-galactopyranosyl-(1→4)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside was also isolated. The corresponding cellobiosamine derivatives were similarly obtained from cellobiose using the same type of catalyst and acceptors. The β-D-galactosidase from bovine testes was found to catalyze the highly specific formation of the β(1→6)-linked derivative Et O-β-galactopyranosyl-(1→6)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside from lactose and Et 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside. Et O-α-L-fucopyranosyl-(1→4)-2-amino-6-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside, suitable as an intermediate for preparation of Lewis-a and related compounds, was obtained from p-nitrophenyl α-L-fucopyranoside and 2-amino-6-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside, employing α-L-fucosidase from bovine testes as catalyst. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Recommanded Product: 130539-43-4

The Article related to galactopyranosylazidodeoxyglucopyranoside fucopyranosylaminodeoxythioglucopyranoside preparation glycosidase, lactose transglycosidation galactosidase, oligosaccharide stereochem preparation glycosidase and other aspects.Recommanded Product: 130539-43-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Qiu, Youai; Fu, Chunling; Zhang, Xue; Ma, Shengming published an article in 2014, the title of the article was Studies on [PtCl2]- or [AuCl]-Catalyzed Cyclization of 1-(Indol-2-yl)-2,3-Allenols: The Effects of Water/Steric Hindrance and 1,2-Migration Selectivity.Safety of 1,5-Dimethyl-1H-indole-2-carbaldehyde And the article contains the following content:

The [PtCl2]- or [AuCl]-catalyzed reaction of 1-(indol-2-yl)-2,3-allenols occurred smoothly at room temperature to afford a series of poly-substituted carbazoles efficiently. Compared with the [PtCl2]-catalyzed process, the [AuCl]-catalyzed reaction represents a significant advance in terms of the scope and the selectivity. Selective 1,2-alkyl or aryl migration of the gold carbene intermediate was observed: compared with the Me group, the iso-Pr, cyclopropyl, cyclobutyl, and cyclohexyl groups migrate exclusively; the cyclopropyl group shifts selectively over the Et group; the 1,2-migration of a non-Me linear alkyl is faster than Me group; the Ph group migrates exclusively over Me or Et group. DFT calculations show that water makes the elimination of H2O facile requiring a much lower energy and validates the migratory preferences of different alkyl or Ph groups observed The experimental process involved the reaction of 1,5-Dimethyl-1H-indole-2-carbaldehyde(cas: 883526-76-9).Safety of 1,5-Dimethyl-1H-indole-2-carbaldehyde

The Article related to cyclization indolylallenols mechanism platinum gold chloride catalyst, dft cyclization indolylallenols platinum gold chloride catalyst, allenes, carbenes, density functional calculations, gold, platinum and other aspects.Safety of 1,5-Dimethyl-1H-indole-2-carbaldehyde

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On April 7, 1998, Arnold, Lee D. published a patent.HPLC of Formula: 52537-00-5 The title of the patent was Preparation of 4-heterocyclylquinazolines as anticancer agents.. And the patent contained the following:

Title compounds [I; Z = specified (substituted) N-heterocyclyl; R1 = CF3, halo, NO2, OH, amino, cyano, alkyl, alkoxy, alkoxycarbonyl, alkanoyloxy, alkanoylamino, CO2H, PhO, PhCO2, carbamoyl, hydroxyalkyl, alkylthio, anilino, pyrrolidinyl, etc.; m = 0-3], were prepared as neoplasm inhibitors (no data). Thus, 6-chloroindoline, 4-chloro-6,7-ethylenedioxyquinazoline, and pyridine were refluxed in iPrOH to give 4-(6-chloro-2,3-dihydroindol-1-yl)-7,8-dihydro[1,4]dioxino[2,3-g]quinazoline. The experimental process involved the reaction of 6-Chloro-2,3-dihydro-1H-indole(cas: 52537-00-5).HPLC of Formula: 52537-00-5

The Article related to heterocyclylquinazoline preparation anticancer, quinazoline heterocyclyl preparation anticancer, hyperproliferative disorder treatment heterocyclylquinazoline, indolylquinazoline preparation anticancer and other aspects.HPLC of Formula: 52537-00-5

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On May 21, 2007, Wang, Ping; Lee, Heeseob; Fukuda, Minoru; Seeberger, Peter H. published an article.Related Products of 130539-43-4 The title of the article was One-pot synthesis of a pentasaccharide with antibiotic activity against Helicobacter pylori. And the article contained the following:

A pentasaccharide that contains the α-1,4-GlcNAc mucin core two-branched O-glycan has been synthesized by a one-pot, two-step glycosylation strategy; this particular carbohydrate motif may provide protection against Helicobacter pylori induced pathologies since the synthetic pentasaccharide inhibits cholesterol α-glucosyltransferase (IC50 of 0.47 mM). The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Related Products of 130539-43-4

The Article related to glycosylation glucosyltransferase inhibitor oligosaccharide synthesis antibacterial, cholesterol glucosyltransferase inhibitor oligosaccharide synthesis antibiotic helicobacter pylori antibacterial and other aspects.Related Products of 130539-43-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On July 8, 2003, Mavunkel, Babu J.; Liu, David Y.; Schreiner, George F.; Lewicki, John A.; Perumattam, John J. published a patent.Reference of 6-Chloro-1H-indole-5-carboxylic acid The title of the patent was Preparation of indoles, benzimidazoles and benztriazoles for treating cardiac failure and other disorders. And the patent contained the following:

The title compounds I and II [Z1, Z2 = CR4, N; R4 = H, alkyl, aryl, each of said alkyl or aryl optionally including one or more heteroatoms selected from O, S and N and optionally substituted by one or more of halo, OR, SR, NR2, RCO, CO2R, CONR2, O2CR, NROCR, etc. and R = H, alkyl; R1 = Q and X1 = CO, SO, SO2, CHOH; m = 1; Y = alkyl, aryl, arylalkyl; YY = alkylene bridge; n = 0-2; Z3 = N; X2 = CH, CH2 or an isostere; Ar = one or two Ph moieties directly coupled to X2 optionally substituted by halo, nitro, alkyl, etc.; R2 = H, alkyl, aryl; R3 = H, halo, NO2, alkyl, alkenyl, etc.], useful as selective inhibitors of p38α kinase, were prepared Thus, amidation of benzimidazole-5-carboxylic acid with 4-benzylpiperidine in the presence of EDAC and DMAP in DMF afforded 47% 4-benzylpiperidinyl-benzimidazole-5-carboxamide which showed 85% inhibition of p38β at 50 μM. The compounds I were tested for their specificity for p38α as compared to p38β (data given). The experimental process involved the reaction of 6-Chloro-1H-indole-5-carboxylic acid(cas: 256935-86-1).Reference of 6-Chloro-1H-indole-5-carboxylic acid

The Article related to benzimidazole preparation p38 kinase inhibitor, heart failure benzimidazole benzotriazole indole preparation, benzotriazole preparation p38 kinase inhibitor, indole preparation p38 kinase inhibitor and other aspects.Reference of 6-Chloro-1H-indole-5-carboxylic acid

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Li, Long; Zhou, Bo; Wang, Yong-Heng; Shu, Chao; Pan, Yi-Fei; Lu, Xin; Ye, Long-Wu published an article in 2015, the title of the article was Zinc-Catalyzed Alkyne Oxidation/C-H Functionalization: Highly Site-Selective Synthesis of Versatile Isoquinolones and β-Carbolines.Recommanded Product: 1,5-Dimethyl-1H-indole-2-carbaldehyde And the article contains the following content:

An efficient zinc(II)-catalyzed alkyne oxidation/C-H functionalization sequence was developed, leading to a highly site-selective synthesis of a variety of isoquinolones, e.g., I, and β-carbolines, e.g., II. Importantly, in contrast to the well-established gold-catalyzed intermol. alkyne oxidation, over-oxidation was completely suppressed in this system and the reaction most likely proceeds by a Friedel-Crafts-type pathway. Mechanistic studies and theor. calculations were described. The experimental process involved the reaction of 1,5-Dimethyl-1H-indole-2-carbaldehyde(cas: 883526-76-9).Recommanded Product: 1,5-Dimethyl-1H-indole-2-carbaldehyde

The Article related to ynamide benzyl alkyne oxidation regioselective functionalization zinc triflate, indolylmethyl ynamide alkyne oxidation regioselective functionalization zinc triflate, isoquinolone preparation, carboline beta preparation, heterocycles, homogeneous catalysis, nitrogen oxides, synthetic methods, zinc and other aspects.Recommanded Product: 1,5-Dimethyl-1H-indole-2-carbaldehyde

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On February 20, 2006, Kuwano, Ryoichi; Kashiwabara, Manabu; Sato, Koji; Ito, Takashi; Kaneda, Kohei; Ito, Yoshihiko published an article.SDS of cas: 79815-20-6 The title of the article was Catalytic asymmetric hydrogenation of indoles using a rhodium complex with a chiral bisphosphine ligand PhTRAP. And the article contained the following:

Nonracemic N-substituted indolines are prepared by enantioselective hydrogenation of N-protected indoles in the presence of a rhodium catalyst generated in situ from bis(norbornadiene)rhodium(I) hexafluoroantimonate and nonracemic bis(diphenylphosphinoethyl)biferrocenes with cesium carbonate as base in isopropanol. Other rhodium precursors such as (μ4-1,5-cyclooctadiene)rhodium (I) acetylacetonate and bases such as triethylamine are effective for the enantioselective hydrogenation of 1-substituted indolines; use of solvents other than isopropanol gives indolines in decreased yields and enantioselectivities or (in the case of methanol) no product. Hydrogenation of 1-acetylindoles with iso-Bu, methoxycarbonyl, Ph, Me or Bu groups at the 2-positions gives the corresponding chiral indolines in 45-98% yields and in 79-95% ee; changing the acetyl group to a tert-butoxycarbonyl or a tosyl group yields indolines in 77-78% ee, while 2-cyclohexyl-1-acetylindole gives the corresponding indoline in 27% yield and 19% ee. Hydrogenation of 3-substituted N-tosylindoles yields 3-substituted 1-tosylindoles; changing the tosyl group to a tert-butoxycarbonyl group decreases enantioselectivity and yield drastically, while replacement of the tosyl group with either a mesyl or a triflyl group gives indoline products with decreased yields and similar enantioselectivities. Me 1-tosyl-3-indolepropanoate, tert-Bu 1-tosyl-3-indoleacetate, and 3-acetyl-1-tosylindole are hydrogenated to indolines in diminished yields and/or selectivities. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).SDS of cas: 79815-20-6

The Article related to indoline enantioselective preparation, stereoselective hydrogenation indole rhodium phenylphosphinoethylbiferrocene catalyst, effect base solvent stereoselective hydrogenation indole rhodium phenylphosphinoethylbiferrocene, catalytic asym hydrogenation indole rhodium complex bisphosphine phtrap and other aspects.SDS of cas: 79815-20-6

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles