Category: 79815-20-6

On January 8, 2003, Viswanathan, Rajesh; Prabhakaran, Erode N.; Plotkin, Michael A.; Johnston, Jeffrey N. published an article.Computed Properties of 79815-20-6 The title of the article was Free Radical-Mediated Aryl Amination and Its Use in a Convergent [3 + 2] Strategy for Enantioselective Indoline α-Amino Acid Synthesis. And the article contained the following:

The scope of aryl radical additions to the nitrogen of azomethines is described. Aryl, trifluoromethyl alkyl, and α,β-unsaturated ketimines engage in regioselective aryl-nitrogen bond formation via 5-exo cyclizations of an aryl radical to azomethine nitrogen. Selectivity for carbon-nitrogen over carbon-carbon bond formation is generally high (>95:5) and competes only with direct aryl radical reduction by stannane (0-10%). α-Ketimines are a promising new class of carbon radical acceptors for which no competitive aryl radical reduction is observed The reaction conditions are pH-neutral and are therefore among the mildest methods available for amination of an aromatic ring. The ketimines examined did not suffer from competitive reduction by stannane, offering an advantage over the use of diazo and azide functional groups as nitrogen sources for carbon radicals. The free radical-mediated aryl amination was sequenced with the O’Donnell phase transfer-catalyzed enantioselective alkylation strategy of glycinyl imine to provide either enantiomer of indoline α-amino acids with high enantiomeric excess. These new constrained Ph alanine derivatives are now readily available for evaluation across a variety of applications. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Computed Properties of 79815-20-6

The Article related to ketimine preparation ketone addition arylamine, indoline derivative preparation radical based aryl amination cyclization ketimine, amino acid indolinecarboxylate asym preparation and other aspects.Computed Properties 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 November 15, 2021, Chen, Xin-Meng; Zhu, Ling; Chen, Dian-Feng; Gong, Liu-Zhu published an article.Category: indole-building-block The title of the article was Chiral Indoline-2-carboxylic Acid Enables Highly Enantioselective Catellani-type Annulation with 4-(bromomethyl)cyclohexanone. And the article contained the following:

Chiral indoline-2-carboxylic acid was identified to enable a highly enantioselective Catellani-type annulation of (hetero)aryl, alkenyl triflate and conjugated vinyl iodides with 4-(bromomethyl)cyclohexanone, directly assembling a diverse range of chiral all-carbon bridged ring systems, e.g., I. Control experiments and DFT calculations suggested that the coordinating orientation of the chiral amino acid to the arylpalladium(II) center allowed for high levels of stereochem. control. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Category: indole-building-block

The Article related to tetrahydro methanocyclooctanaphthalenone enantioselective preparation, enantioselective preparation tetrahydro methanocyclooctaquinolinedione, c−h activation, asymmetric catellani annulation, chiral amines, cooperative catalysis, palladium 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

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 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

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 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 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 July 1, 2010, Suga, Hiroyuki; Arikawa, Tadashi; Itoh, Kennosuke; Okumura, Yukihisa; Kakehi, Akikazu; Shiro, Motoo published an article.Category: indole-building-block The title of the article was Asymmetric 1,3-dipolar cycloaddition reactions of azomethine imines with acrolein catalyzed by L-proline and its derivatives. And the article contained the following:

1,3-Dipolar cycloadditions between acrolein and various N,N’-cyclic azomethine imines in the presence of L-proline and its derivatives as organocatalysts were investigated. Reactions that were catalyzed by (S)-indoline-2-carboxylate (30 mol%) in CHCl3/MeOH 97:3 (volume/volume) showed high exo-selectivities (exo/endo 91:9∼99:1) and enantioselectivities (75∼98% ee). In contrast, reactions catalyzed by L-proline (30 mol%) under similar conditions favored the endo-cycloadduct (83:27∼99:1) with modest to good enantioselectivities (31∼83% ee). The diastereoselective mechanism of the L-proline-catalyzed reaction was found to involve the isomerization of the exo- to the endo-cycloadduct in the presence of L-proline. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Category: indole-building-block

The Article related to azomethine imine acrolein asym dipolar cycloaddition proline catalyst, indolinecarboxylate catalyst asym dipolar cycloaddition azomethine imine acrolein, hydropyrazolopyrazole asym synthesis isomerization, pyrazolopyrazole hydro asym synthesis isomerization 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

Hayashi, Shigeo; Ohashi, Katsuyo; Nakata, Eriko; Emoto, Chie published an article in 2012, the title of the article was Discovery of 1-(β-amino substituted-β-alanyl)-N,N-dimethylindoline-2-carboxamides as novel nonpeptide antagonists of nociceptin/orphanin FQ receptor: Efficient design, synthesis, and structure-activity relationship studies.SDS of cas: 79815-20-6 And the article contains the following content:

Since the discovery of endogenous nociceptin/orphanin FQ (N/OFQ) peptide and N/OFQ peptide (NOP) receptor [or opioid-receptor-like-1 (ORL1) receptor], the structures, distribution, and pharmacol. have been reported in detail. N/OFQ and NOP receptor are located in the corticolimbic regions that are involved in the integration of the emotional activity, and located in the spinal cord, the peripheral nervous systems or other peripheral tissues that are related to pain as well as urinary signal transmissions, with a pattern distinct from that of classical opioid peptides and their receptors in rodents or primates. Furthermore, N/OFQ-NOP receptor system plays an important role in the regulation of various human physiologies such as depression effect, hyperphasia effect, and blood pressure effect. In this study, the structure-activity relationship of novel NOP receptor antagonist for various 1-(β-amino substituted-β-alanyl)-N,N-dimethylindoline-2-carboxamides was investigated in vitro to elucidate structural requisites to identify and develop potent and selective NOP receptor antagonists, which resulted in the discovery of 1-{3-[4-(substituted phenyl)piperidin-1-yl]propanoyl}-N,N-dimethylindoline-2-carboxamide analogs that display potent and selective human NOP (hNOP) receptor binding affinity and potent hNOP receptor antagonist activity. The efficient design, synthesis, and structure-activity relationship studies for potent and selective novel NOP receptor antagonists and significant findings in vitro, that include insights for binding and functional mechanisms via receptor-ligand interactions, are reported herein. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).SDS of cas: 79815-20-6

The Article related to peptidomimetic synthesis nofq nop receptor antagonist structure activity pharmacokinetics, amino alanyl dimethylindoline carboxamide parallel synthesis metabolic stability lipophilicity, indoline carboxylic acid amidation amine michael addition drug design 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