Day: October 26, 2022

On September 21, 2016, Ji, Pengfei; Manna, Kuntal; Lin, Zekai; Urban, Ania; Greene, Francis X.; Lan, Guangxu; Lin, Wenbin published an article.Application In Synthesis of 6-Chloro-2,3-dihydro-1H-indole The title of the article was Single-Site Cobalt Catalysts at New Zr8(μ2-O)8(μ2-OH)4 Metal-Organic Framework Nodes for Highly Active Hydrogenation of Alkenes, Imines, Carbonyls, and Heterocycles. And the article contained the following:

Zirconium and hafnium metal-organic frameworks (MOF) were prepared from a tetrakis(carboxybiphenyl)methane and ZrCl4 or HfCl4; the framework contains two types of secondary building units (SBUs): cubic M8(μ2-O)8(μ2-OH)4 and octahedral M6(μ3-O)4(μ3-OH)4. While the M6-SBU is isostructural with the 12-connected octahedral SBUs of UiO-type MOFs, the M8-SBU is composed of eight MIV ions in a cubic fashion linked by eight μ2-oxo and four μ2-OH groups. Metalation of the Zr-MTBC MOF with CoCl2 followed by treatment with NaBEt3H yielded a highly active and reusable solid Zr-MOF-cobalt hydride catalyst for the hydrogenation of alkenes, imines, carbonyls, and heterocycles. The Zr-MOF-cobalt hydride catalyst tolerated a range of functional groups and was a highly active catalyst for the hydrogenation of alkenes, including tri- and tetra-substituted alkenes, with TON > 8000 for the hydrogenation of 2,3-dimethyl-2-butene. Structural and spectroscopic studies indicate that the site isolation of and open environments around the cobalt-hydride catalytic species at the cubic zirconium SBU sites of the MOF are responsible for the high catalytic activity in the hydrogenation of a wide range of challenging substrates. The structures of the zirconium and hafnium MOF and of the cobalt chloride complex of the zirconium MOF were determined by X-ray crystallog. The experimental process involved the reaction of 6-Chloro-2,3-dihydro-1H-indole(cas: 52537-00-5).Application In Synthesis of 6-Chloro-2,3-dihydro-1H-indole

The Article related to zirconium hafnium tetrakiscarboxybiphenylmethane metal organic framework preparation hydrogenation catalyst, structure secondary building unit zirconium hafnium tetrakiscarboxybiphenylmethane mof, cobalt zirconium mof complex preparation chemoselective hydrogenation catalyst and other aspects.Application In Synthesis of 6-Chloro-2,3-dihydro-1H-indole

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 October 31, 2002, Nowak, Ireneusz; George, Clifford published an article.Quality Control of H-Idc-OH The title of the article was Stereoselective dimerization of benzylic amines derived from indoline. And the article contained the following:

Treatment of benzylic amines derived from 2-(acyloxymethyl)-5-nitroindolines with sodium hexamethyldisilazide leads to dimeric products resulting from deprotonation in the benzylic position, oxidation of the resulting carbanion to radical by the nitroarene moiety of another mol., and stereoselective radical recombination. Only those two of six possible diastereoisomers are formed in which the recombination takes place from the less hindered face in the more stable conformation of the presumably near-planar radical. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Quality Control of H-Idc-OH

The Article related to stereoselective dimerization benzylic amine indoline derivative, crystal structure bishalophenylethanediylbisindolemethanol preparation, mol structure bishalophenylethanediylbisindolemethanol preparation, radical dimerization stereochem benzylindollemethanol ester preparation and other aspects.Quality Control of H-Idc-OH

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 15, 2020, Balayeva, Narmina O.; Mamiyev, Zamin; Dillert, Ralf; Zheng, Nan; Bahnemann, Detlef W. published an article.Application of 79815-20-6 The title of the article was Rh/TiO2-Photocatalyzed Acceptorless Dehydrogenation of N-Heterocycles upon Visible-Light Illumination. And the article contained the following:

Rh-photodeposited TiO2 nanoparticles selectively dehydrogenate N-heterocyclic amines I (R1 = H, 6-Me, 7-OH, etc.; R2 = H, 2-Me, 2-Ph-4-MeS), II (R3 = H, 6,7-dimethoxy; R4 = H, Ph, Me) and III (R5 = H, trifluoromethyl; R6 = H, Me, COOH, COOMe, etc.) with the concomitant generation of mol. hydrogen gas in an inert atm. under visible light (λmax = 453 nm) illumination at room temperature Initially, a visible-light-sensitive surface complex is formed between the N-heterocycle and TiO2. The acceptorless dehydrogenation of N-heterocycles is initiated by direct electron transfer from the HOMO energy level of the amine via the conduction band of TiO2 to the Rh nanoparticle. The reaction condition was optimized by examining different photodeposited noble metals on the surface of TiO2 and solvents and finding that Rh0 is the most efficient cocatalyst, and 2-propanol is the optimal solvent. Structurally diverse N-heterocycles such as tetrahydroquinolines I, tetrahydroisoquinolines II, indolines III, and others bearing electron-deficient as well as electron-rich substituents underwent the dehydrogenation in good to excellent yields. The amount of released hydrogen gas evinces that only the N-heterocyclic amines are oxidized rather than the dispersant. This developed method demonstrates how UV-active TiO2 can be employed in visible-light-induced synthetic dehydrogenation of amines and simultaneous hydrogen storage applications. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Application of 79815-20-6

The Article related to quinoline preparation, tetrahydroquinoline photochem dehydrogenation rhodium titanium dioxide catalyst, tetrahydroisoquinoline photochem dehydrogenation rhodium titanium dioxide catalyst, indole preparation, indoline photochem dehydrogenation rhodium titanium dioxide catalyst and other aspects.Application of 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

On June 15, 2016, Wang, Guangyong; Li, Chaoping; Zhou, Zhiguo; Gao, Qiang; Zheng, Baofu published a patent.Name: Methyl 2-methyl-1H-indole-3-carboxylate The title of the patent was Synthetic method of histone methylation enzyme EZH2 inhibitor intermediate. And the patent contained the following:

The invention relates to the synthetic method of histone methylation enzyme EZH2 inhibitor intermediate. The title synthetic method includes (1) mixing compound 1 (Z is NH, NBoc, O, etc.) with reducing agent ((R)-MeCBS-borane dimethylsulfide, sodium borohydride, etc.) in solvent (methanol, ethanol, etc.) at (-10)-0°C, stirring at 0-5°C for 10 min, quenching with hydrochloric acid at (-5)-0°C, adding Me tert-Bu ether, stirring, filtering, layering, extracting water phase with Me tert-Bu ether, collecting organic phase, washing with saturated brine, drying, filtering, and concentrating to obtain compound 2; (2) reacting with methanesulfonyl chloride in presence of base (triethylamine, N,N-diisopropylethylamine, etc.) to obtain compound 3; (3) performing nucleophilic substitution reaction with compound 4 in organic solvent (N,N-dimethylformamide, N,N-dimethylaniline, etc.) in presence of base (sodium hydrogen, sodium carbonate, etc.) at 80-130°C to obtain compound 5; and (4) performing hydrolysis. The preparation method has high product yield, simple process, convenient post treatment, readily available raw materials and environment friendliness. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Name: Methyl 2-methyl-1H-indole-3-carboxylate

The Article related to acetyl heterocycloalkane asym reduction, hydroxy ethyl heterocycloalkane stereoselective preparation methanesulfonylation, mesylate preparation indolecarboxylate nucleophilic substitution hydrolysis, histone methylation enzyme ezh2 inhibitor intermediate preparation green chem and other aspects.Name: Methyl 2-methyl-1H-indole-3-carboxylate

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 16, 2018, Kong, Xiang-Fei; Zhan, Feng; He, Guo-Xue; Pan, Cheng-Xue; Gu, Chen-Xi; Lu, Ke; Mo, Dong-Liang; Su, Gui-Fa published an article.HPLC of Formula: 883526-76-9 The title of the article was Gold-Catalyzed Selective 6-exo-dig and 7-endo-dig Cyclizations of Alkyne-Tethered Indoles To Prepare Rutaecarpine Derivatives. And the article contained the following:

An efficient method to synthesize rutaecarpine derivatives I [R1 = H, OMe-3, Me-3, Cl-3, Br-3, I-3, F-2, Cl-4; R2 = Me, CH2Ph, H; R3 = Me-10, Br-10, Cl-11; R4 = H, Me, SiMe3] and II [R1 = H, OMe, Cl, Br, I; R3 = H, Cl; R4 = H, Me, Ph, SiMe3] via the gold-catalyzed selective cyclization of alkyne-tethered indoles III under mild conditions is described. The alkyne-tethered indole can undergo 6-exo-dig cyclization by oxidation and sequential gold catalysis, while it goes through 7-endo-dig cyclization by gold catalysis and sequential oxidation Substrate scope studies reveal that the selectivity of cyclization was controlled by the substrates with sp3 and sp2 hybridization of carbon at the 2 position in quinazolinone. Furthermore, the rutaecarpine scaffold was prepared in 67% yield at gram scale easily in four steps from isatoic anhydride. The experimental process involved the reaction of 1,5-Dimethyl-1H-indole-2-carbaldehyde(cas: 883526-76-9).HPLC of Formula: 883526-76-9

The Article related to rutaecarpine alkaloid derivative scaffold preparation, quinazolinone alkyne tethered indoles gold catalyzed selective cyclization, exo dig cyclization gold catalysis quinazolinone alkyne tethered indoles, endo dig cyclization gold catalysis quinazolinone alkyne tethered indoles and other aspects.HPLC of Formula: 883526-76-9

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

Zhong, Sabilla; Wandler, Angela E. E.; Schepers, Ute; Nieger, Martin; Braese, Stefan published an article in 2015, the title of the article was Synthesis of New Diketopiperazines, Thiolation to Thiodiketopiperazines, and Examination of Their ROS-Generating Properties.Synthetic Route of 79815-20-6 And the article contains the following content:

A variety of new sym. and unsym. diketopiperazines have been prepared from free amino acids by using a previously developed microwave-assisted protocol. This included the successful incorporation of L-pyroglutamic acid as an unusual building block. The diketopiperazines were then thiolated electrophilically to the corresponding bis(methylthio)- and epidithiodiketopiperazines, e.g., I and II (X = S2, S3). Initial experiments showed a promising activity towards the generation of reactive oxygen species in HeLa cells. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Synthetic Route of 79815-20-6

The Article related to amino acid microwave irradiation dimerization, diketopiperazine stereoselective preparation sulfur thiolation reduction, bis methylthio diketopiperazine stereoselective preparation ros generation activity, epidithiodiketopiperazine stereoselective preparation ros generation activity and other aspects.Synthetic Route of 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

On July 20, 2007, Hartikka, Antti; Arvidsson, Per I. published an article.Synthetic Route of 79815-20-6 The title of the article was Tetrazolic Acid Functionalized Dihydroindol: Rational Design of a Highly Selective Cyclopropanation Organocatalyst. And the article contained the following:

An improved catalyst (S)-(-)-indolin-2-yl-1H-tetrazole (I) for the enantioselective organocatalyzed cyclopropanation of α,β-unsaturated aldehydes with sulfur ylides has been reported. The new organocatalyst readily facilitates the enantioselective organocatalytic cyclopropanation, providing cyclized products, e.g., II, in excellent diastereoselectivities ranging from 96% to 98% along with enantioselectivities exceeding 99% enantiomeric excess for all reacted α,β-unsaturated aldehydes. The new catalyst provides the best results so far reported for intermol. enantioselective organocatalyzed cyclopropanation. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Synthetic Route of 79815-20-6

The Article related to unsaturated aldehyde sulfur ylide chiral indolinyltetrazole diastereoselective enantioselective cyclopropanation, cyclopropane carboxaldehyde derivative stereoselective preparation, intermol diastereoselective enantioselective cyclopropanation organocatalyst chiral indolinyltetrazole and other aspects.Synthetic Route of 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

On August 31, 1995, Arnold, Lee D. published a patent.Electric Literature of 52537-00-5 The title of the patent was Preparation of 4-(heterocyclyl)quinazoline-derivative anticancer agents. And the patent contained the following:

The title compds [I; R1 = (un)substituted alkyl, halogen, NO2, OH, NH2, alkoxy, heterocyclo, PhO, etc.; Z = (un)substituted heterocyclo; m = 0-3], useful for the treatment of abnormal proliferation due to cancer (no data), psoriasis (no data), benign prostatic hypertrophy (no data), etc. (no data), are prepared Thus, 6-chloroindoline was reacted with 4-chloro-6,7-(ethylenedioxy)quinazoline and pyridine, producing 4-(6-chloro-2,3-dihydroindol-1-yl)-7,8-dihydro[1,4]dioxino[2,3-g]quinazoline, m.p. 209-211°. The experimental process involved the reaction of 6-Chloro-2,3-dihydro-1H-indole(cas: 52537-00-5).Electric Literature of 52537-00-5

The Article related to anticancer agent preparation heterocyclylquinazoline, psoriasis treatment preparation heterocyclylquinazoline, benign prostatic hypertrophy treatment preparation heterocyclylquinazoline, cell proliferation abnormal prevention preparation heterocyclylquinazoline, quinazoline heterocyclyl and other aspects.Electric Literature of 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 June 30, 2008, Vesely, Jan; Zhao, Gui-Ling; Bartoszewicz, Agnieszka; Cordova, Armando published an article.Category: indole-building-block The title of the article was Organocatalytic asymmetric nitrocyclopropanation of α,β-unsaturated aldehydes. And the article contained the following:

A novel organocatalytic, highly enantioselective nitrocyclopropanation of α,β-unsaturated aldehydes is presented. The 1-nitro-2-formylcyclopropane derivatives synthesized from this catalytic transformation were converted to the corresponding β-nitromethyl-acid esters, which are excellent precursors of GABA analogs such as baclofen, by subsequent organocatalytic, chemoselective ring-opening. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Category: indole-building-block

The Article related to unsaturated aldehyde bromonitromethane stereoselective nitrocyclopropanation organocatalyst, nitrocyclopropanecarboxaldehyde stereoselective preparation ring opening, nitro ester baclofen precursor stereoselective preparation, gaba analog precursor nitro ester stereoselective preparation and other aspects.Category: indole-building-block

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