Day: October 26, 2022

On September 2, 2016, Lian, Xiao-Lei; Meng, Jing; Han, Zhi-Yong published an article.COA of Formula: C8H8ClN The title of the article was Ru(II)/Organo Relay Catalytic Three-Component Reaction of 3-Diazooxindoles, Amines, and Nitroalkene: Formal Synthesis of (-)-Psychotrimine. And the article contained the following:

A highly enantioselective carbenoid-associated N-H functionalization/Michael addition cascade reaction is developed by virtue of Ru(II)/chiral organo bifunctional catalyst relay catalysis. In this way, a variety of optically pure 3-amino-3-alkyloxindoles, I (R1 = H, 5-MeO, 5-Me, 5-Cl, 5-F, 6-Br, 7-Br, R2R3N = indolin-1-yl, 6-chloroindolin-1-yl, N-benzylphenylamino, etc.) can be easily achieved. Moreover, on the basis of this metal/organo relay catalytic three-component protocol, key intermediate II, for the formal synthesis of (-)-psychotrimine, could be obtained in six steps with 25% overall yield. The experimental process involved the reaction of 6-Chloro-2,3-dihydro-1H-indole(cas: 52537-00-5).COA of Formula: C8H8ClN

The Article related to relay catalytic three component reaction diazooxindole amine nitroalkene ruthenium, enantioselective synthesis psychotrimine, stereoselective michael addition cascade ruthenium chiral organo bifunctional catalyst and other aspects.COA of Formula: C8H8ClN

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 15, 2018, Uredi, Dilipkumar; Motati, Damoder Reddy; Watkins, E. Blake published an article.Recommanded Product: 1,5-Dimethyl-1H-indole-2-carbaldehyde The title of the article was A Unified Strategy for the Synthesis of β-Carbolines, γ-Carbolines, and Other Fused Azaheteroaromatics under Mild, Metal-Free Conditions. And the article contained the following:

An efficient, unified approach for the synthesis of β-carbolines, γ-carbolines, and other fused azaheteroaroms. has been realized under metal-free conditions, from propargylic amines and (hetero)aromatic aldehydes. This unified strategy provides β- and γ-carbolines as well as a range of fused azaheteroaroms. with a broad substrate scope and excellent functional group compatibility. The formal synthesis of oxopropalines D and G has been achieved on gram scale using I, in a one-pot reaction from com. available materials (previous shortest reported route to I was 5 steps). NMR studies of the conversion of imine intermediate II to β-carboline I were conducted and revealed that the reaction proceeded through an allene intermediate. 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 propargylic amine heteroaromatic aldehyde isomerization azacyclization proton shift, carboline preparation metal free, fused azaheteroarom preparation, oxopropalines d formal synthesis, formal synthesis oxopropalines g 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 June 2, 2017, Li, Long; Chen, Xiu-Mei; Wang, Ze-Shu; Zhou, Bo; Liu, Xin; Lu, Xin; Ye, Long-Wu published an article.Category: indole-building-block The title of the article was Reversal of Regioselectivity in Catalytic Arene-Ynamide Cyclization: Direct Synthesis of Valuable Azepino[4,5-b]indoles and β-Carbolines and DFT Calculations. And the article contained the following:

Ynamides are important building blocks in organic synthesis, and a variety of versatile synthetic methods have been developed in the past decade. Among these, catalytic cyclizations of π-tethered ynamides are particularly attractive, since this approach enables facile access to a diverse array of synthetically useful nitrogen heterocycles. However, due to the fact that the nitrogen atom is able to impose an electronic bias, these cyclizations exclusively occur on the α position of ynamides. Herein, we report the reversal of regioselectivity in arene-ynamide cyclization by copper catalysis, which represents the first catalytic π-tethered ynamide cyclization involving the reversal of regioselectivity. This strategy allows the expedient and practical synthesis of valuable azepino[4,5-b]indoles and β-carbolines in generally high yields under mild conditions. Moreover, the relevant mechanistic rationale for this cyclization, especially for the observed high regioselectivity, is strongly supported by d. functional theory (DFT) calculations The synthetic utility of this chem. is also indicated by the synthesis of several biol. active compounds and natural product bauerine A. The experimental process involved the reaction of 1,5-Dimethyl-1H-indole-2-carbaldehyde(cas: 883526-76-9).Category: indole-building-block

The Article related to crystal mol structure azepino indole carboline, carboline preparation regioselective reversal catalytic tethered ynamide cyclization, azepino indole preparation regioselective reversal catalytic tethered ynamide cyclization 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

Wani, Imtiyaz Ahmad; Bhattacharyya, Aditya; Sayyad, Masthanvali; Ghorai, Manas K. published an article in 2018, the title of the article was Temperature-modulated diastereoselective transformations of 2-vinylindoles to tetrahydrocarbazoles and tetrahydrocycloheptadiindoles.Application In Synthesis of 1,5-Dimethyl-1H-indole-2-carbaldehyde And the article contains the following content:

Direct and expedient access to densely substituted tetrahydrocarbazoles I [R1 = H, F; R2 = H, Me, CH2CH:CH2; R3 = OMe, OEt, Ph] and tetrahydrocycloheptadiindoles bearing multiple contiguous stereocenteres II [R1 = H, F, Cl, Me] were achieved via a two-fold divergent diastereoselective (dr up to >99:1) transformation of 2-vinylindoles. The high-yielding conversions (yield up to 87%) that were amenable for a wide range of substituted 2-vinylindoles proceeded through Lewis acid-catalyzed [4 + 2] and [4 + 3] cyclization-aromatization cascade reactions, resp., involving a heretofore-unprecedented reversal of the polarity (umpolung) of 2-vinylindoles. The two synthetic routes were effortlessly transposable into each other by merely modulating the temperature to furnished the corresponding products in a selective and exclusive fashion. In addition, another novel synthetic route to tetrahydroindolocarbazoles was developed that advances via a formal [4+2] cyclization of 4-vinylindoles involving sequential C3 Michael addition-dearomatization-aromatization cascade reactions. Diastereo- and chemoselective preparation of tetrahydrocarbazoles and tetrahydrocycloheptadiindoles via Fe(OTf)3 catalyzed tandem cyclization-aromatization of vinylindoles. The experimental process involved the reaction of 1,5-Dimethyl-1H-indole-2-carbaldehyde(cas: 883526-76-9).Application In Synthesis of 1,5-Dimethyl-1H-indole-2-carbaldehyde

The Article related to tetrahydrocarbazole preparation diastereoselective chemoselective, tetrahydrocycloheptadiindole preparation diastereoselective chemoselective, vinylindole iron trifluoromethanesulfonate catalyst tandem cyclization aromatization and other aspects.Application In Synthesis 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 November 27, 2014, Armer, Richard; Bingham, Matilda; Morrison, Angus; Carswell, Emma; Elustondo, Fred; Walker, Rolf; Guisot, Nicolas; Lucas, Catherine published a patent.Related Products of 52537-00-5 The title of the patent was Preparation of pyrazolo[3,4-d]pyrimidine derivatives useful as inhibitors of Bruton’s tyrosine kinase. And the patent contained the following:

This invention relates to novel compounds [I; A1-A5 = N or CRa and any two CRa on adjacent A groups form an addnl. (un)substituted nonaromatic carbocyclic or heterocyclic ring; D = (un)substituted C1-6 alkylene optionally containing 1, 2 or 3 N, O, or S atoms; or D = (un)saturated and (un)substituted carbocyclic or heterocyclic moiety optionally substituted with NRb; E = C(:Y)C(R2):C(R4)(R3), SO2 C(R2):C(R4)(R3), cyano, COCH2X, (oxiran-2-yl)(CH2)o, or (oxiran-2-yl)(CH2)oCO; Y = O or NRb; X = Cl, F, Br, or iodo; o = 0-2; Ra = H, halo, C1-6 alkyl, C1-6 haloalkyl, OH, SH, C1-6 alkoxy, C2-6 alkenyl, C2-6 alkynyl, C3-8 cycloalkyl, C3-8 cycloalkenyl, NRbRc, cyano, acyl, etc.; Rb, Rc = H, C1-4 alkyl, C1-4 haloalkyl, C1-4 acyl, C3-7 cycloalkyl, or C3-7 halocycloalkyl; R1 = each (un)substituted NH2 or each (un)saturated carbocyclic or heterocyclic moiety; R2, R3, R4 = H, halo , ORb, cyano, -NRbRc, -CH2NRbRc, CO2Rb, C(O)Rbb, C(O)NRbRc, etc.; R5 = H, halo, ORb, C1-6 alkoxy, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 haloalkyl, C3-8 cycloalkyl, C3-8 heterocycloalkyl, C3-8 cycloalkenyl, C3-8 heterocycloalkenyl, NRbRc, -CO2Rb, C(O)Rb, or C(O)NRbRc; L1 = a bond, O, or each (un)substituted O(CH2)m, NH, or (CH2)m; m = 1, 2, 3, or 4]. These compounds are Bruton’s tyrosine kinase (BTK) inhibitors and have better activity and better solubility over known compounds, reduced side effects compared to known therapies, convenient pharmacokinetic profile, and a suitable duration of action following dosing. They are useful for treating conditions treatable by the inhibition of Bruton’s tyrosine kinase, for example cancer, lymphoma, leukemia, immunol. diseases, autoimmune diseases, and inflammatory disorders. Thus, Mitsunobu reaction of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine with and tert-Bu (3S)-3-hydroxypiperidine-1-carboxylate using Ph3P and DIAD in THF at <5° for 30 min and at room temperature overnight gave tert-Bu 3-(4-amino-3-iodopyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate which underwent Suzuki coupling with 4-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]morpholine in the presence of potassium carbonate and tetrakis(triphenylphosphine)palladium in aqueous dioxane at 100° for 60 min under microwave irradiation to give tert-Bu 3-[(1S)-4-amino-3-[4-(morpholinomethyl)phenyl]pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate (II; R = tert-butoxycarbonyl). Deprotection of II (R = tert-butoxycarbonyl) with 4 M HCl/dioxane solution for 4 h gave II.HCl (R = H) which underwent acylation with acryloyl chloride in the presence of Et3N at room temperature for 2 h to give II (R = acryloyl). II (R = acryloyl) showed IC50 of 0.1-15 nM against Bruton's tyrosine kinase. The experimental process involved the reaction of 6-Chloro-2,3-dihydro-1H-indole(cas: 52537-00-5).Related Products of 52537-00-5

The Article related to pyrazolopyrimidine preparation inhibitor bruton tyrosine kinase, cancer lymphoma leukemia immunol disease treatment pyrazolopyrimidine preparation, autoimmune disease inflammatory disorder treatment pyrazolopyrimidine preparation and other aspects.Related Products 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 January 3, 2022, Shaaban, Saad; Merten, Christian; Waldmann, Herbert published an article.Electric Literature of 52537-00-5 The title of the article was Catalytic Atroposelective C7 Functionalisation of Indolines and Indoles. And the article contained the following:

Axially chiral atropisomeric compounds are widely applied in asym. catalysis and medicinal chem. In particular, axially chiral indole- and indoline-based frameworks have been recognized as important heterobiaryl classes because they are the core units of bioactive natural alkaloids, chiral ligands and bioactive compounds Among them, the synthesis of C7-substituted indole biaryls and the analogous indoline derivatives is particularly challenging, and methods for their efficient synthesis are in high demand. Transition-metal catalysis is considered one of the most efficient methods to construct atropisomers. Here, authors report the enantioselective synthesis of C7-indolino- and C7-indolo biaryl atropisomers by means of C-H functionalisation catalyzed by chiral RhJasCp complexes. 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 indolino indolo biaryl atropisomer preparation enantioselective, methoxyindolinecarboxamide indolobenzamide diazonaphthoquinone coupling rhodium, c−h functionalisation, atropisomers, chiral cpx complexes, indoles, indolines, rhodium 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

Cui, Xin; Huang, Wei; Wu, Lipeng published an article in 2021, the title of the article was Zirconium-hydride-catalyzed transfer hydrogenation of quinolines and indoles with ammonia borane.Computed Properties of 52537-00-5 And the article contains the following content:

Applied zirconium-hydride complex as the catalyst, the transfer hydrogenation of quinoline and indole derivatives with ammonia borane as a proton and hydride source was achieved. Up to 94% yield of the corresponding hydrogenated products were obtained with tolerance of various functional groups. Preliminary mechanistic studies revealed a concerted N-H and B-H activation reaction pathway. The experimental process involved the reaction of 6-Chloro-2,3-dihydro-1H-indole(cas: 52537-00-5).Computed Properties of 52537-00-5

The Article related to quinoline ammonia borane zirconium hydride catalyst regioselective transfer hydrogenation, tetrahydroquinoline preparation, indole ammonia borane zirconium hydride catalyst regioselective transfer hydrogenation, indoline preparation and other aspects.Computed Properties 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 March 31, 1991, Peters, Thomas; Weimar, Thomas published an article.Formula: C16H19NO6S The title of the article was Improved synthesis of α-L-Fuc(1 → 4)-β-D-GlcNAc and α-L-Fuc(1 → 6)-β-D-GlcNAc building blocks: a convergent strategy employing 4-O → 6-O acetyl migration; NOE data on protected α-1,4-linked disaccharides. And the article contained the following:

The synthesis of the two thioethyl disaccharide building blocks I (R1 = PhCH2, R2 = Ac, R3 = phthalimido, R4 = SEt) and II (same R1-R4) was achieved via coupling of fucosyl bromide III with the acceptor alcs. IV (R5 = Ac, R6 = H) and IV (R5 = H, R6 = Ac) under in situ anomerization conditions. The selectively protected 2-deoxy-2-phthalimidoglucose derivative IV (R5 = H, R6 = Ac) was derived from by utilizing an optimized acetyl migration reaction. The thioethyl function in disaccharides I and II was activated with bromine, and excess bromine was removed with cyclohexene. The sensitive 1,6-linkage in the disaccharide I proved to be stable under these activating conditions. The disaccharide bromides I (R1 = CH2Ph, R2 = Ac, R3 = phthalimido, R4 = Br) and II (R1 = CH2Ph, R2 = Ac, R3 = phthalimidi, R4 = Br) were treated with methanol to afford after deblocking the Me glycosides I (R1 = R2 = H, R3 = AcNH, R4 = OMe) and II (R1 = R2 = H, R3 = AcNH, R4 = OMe). Homonuclear 1H-NOE data were obtained for the protected 1,4-linked disaccharide II (R1 = PhCH2, R2 = Ac, R3 = phthalimido, R4 = SEt) suggesting that its preferred solution conformation is rather similar to the solution conformation of the deblocked disaccharide II (R1 = R2 = H, R3 = AcNH, R4 = OMe) in aqueous solution as known from literature data. 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).Formula: C16H19NO6S

The Article related to fucosyl bromide glycosidation thioglycoside, fucosylglucosamine thioglycoside building block, disaccharide thioglycoside building block, deoxyphthalimidoglucose glycosidation fucosyl bromide, conformation disaccharide glycoside linkage and other aspects.Formula: C16H19NO6S

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 27, 2021, Wyand, Michael; Swiss, Gerald F. published a patent.Formula: C16H19NO6S The title of the patent was Low contaminant vaccines against microbes possessing a cell wall structure comprising poly-β-(1→6)-glucosamine (PNAG). And the patent contained the following:

Disclosed are antimicrobial vaccines (A-B)x-C, wherein A comprises 3 to 12 3-(1→6)-glucosamine I (carbohydrate ligand) groups; B is a linker; C is tetatus toxoid; x is an integer from about 30 to about 39; n is an integer from 1 to 10, wherein less than about 40% of the total number of such units are N-acetylated. 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).Formula: C16H19NO6S

The Article related to glucosamine pnag antimicrobial vaccine oligosaccharide preparation human fpa91, antimicrobial vaccine cell wall glucosamine oligosaccharide burn therapy, vaccine oligosaccharide glucsosamine tetanus toxoid carrier f598 monoclonal antibody and other aspects.Formula: C16H19NO6S

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