Category: 69622-40-8

Ito, Yoshihiko published the artcileIndole syntheses with o-tolyl isocyanide. 3-Acylindoles and 2-substituted indoles, Safety of 2-(tert-Butyl)-5-chloro-1H-indole, the main research area is indole acyl; tolyl isocyanide acylation; cyclization acylmethylphenyl isocyanide.

o-(Lithiomethyl)phenyl isocyanide, generated from o-tolyl isocyanide and (Me2CH)2NLi in diglyme, reacts with allyl esters to produce o-(acylmethyl)phenyl isocyanides. Similarly, acylation of 4-chloro-2-methylphenyl isocyanide, 2,4-dimethylphenyl isocyanide, and 2,6-dimethylphenyl isocyanide produces the corresponding o-(acylmethyl)phenyl isocyanides in moderate yields. o-(Acylmethyl)phenyl isocyanides are heated with Cu2O catalyst in benzene to give 3-acylindole. o-(Acylmethyl)phenyl isocyanides are hydrolyzed to afford 2-alkyl(or 2-aryl)indoles.

Journal of Organic Chemistry published new progress about Cyclization. 69622-40-8 belongs to class indole-building-block, name is 2-(tert-Butyl)-5-chloro-1H-indole, and the molecular formula is C12H14ClN, Safety of 2-(tert-Butyl)-5-chloro-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

McKew, John C. published the artcileInhibition of Cytosolic Phospholipase A2α: Hit to Lead Optimization, Quality Control of 69622-40-8, the main research area is indole derivative preparation structure phospholipase A2 inhibitor.

Compound (I) was previously reported to be a potent inhibitor of cPLA2α in both artificial monomeric substrate and cell-based assays. However, I was inactive in whole blood assays previously used to characterize cyclooxygenase and lipoxygenase inhibitors. The IC50 of I increased dramatically with cell number or lipid/detergent concentration In an attempt to insert an electrophilic ketone between the indole and benzoic acid moieties, the authors discovered that increasing the distance between the two moieties gave a compound with activity in the GLU (7-hydroxycoumarinyl-γ-linolenate) micelle assay, which contains lipid and detergent. Extensive structure-activity relationship work around this lead identified a potent pharmacophore for cPLA2α inhibition. The IC50s between the GLU micelle and rat whole blood assays correlated highly. No correlation was found for other parameters, including lipophilicity or acidity of the required acid functionality. Three compounds emerged as potent, selective inhibitors of cPLA2α and represent well-validated starting points for further optimization.

Journal of Medicinal Chemistry published new progress about Pharmacophores. 69622-40-8 belongs to class indole-building-block, name is 2-(tert-Butyl)-5-chloro-1H-indole, and the molecular formula is C12H14ClN, Quality Control of 69622-40-8.

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

Smith, Keith published the artcileCarbonylation of various organolithium reagents. A novel approach to heterocycles via intramolecular trapping of aromatic acyllithiums, Related Products of indole-building-block, the main research area is pivaloylaniline pivaloylaminopyridine carbonylation; pivaloyltoluidine carbonylation; cyclization carbonylation pivaloylaniline pivaloylaminopyridine; indole preparation cyclization carbonylation pivaloylaniline pivaloylaminopyridine.

Doubly lithiated N-pivaloylanilines react smoothly with carbon monoxide at 0 °C to give 3-tert-butyl-3-hydroxy-2,3-dihydro-2-indolones in good yields. Similarly, carbonylation of doubly lithiated 4-pivaloylamino- and 2-pivaloylaminopyridines at 0 °C affords the corresponding 5-aza- and 7-aza-3-tert-butyl-3-hydroxy-2,3-dihydro-2-indolones, resp., in good yields. However, carbonylation of doubly lithiated N-pivaloyl-o-toluidines takes a different course due to direct intramol. cyclization of the dilithio reagents to afford 2-tert-butylindoles without uptake of carbon monoxide.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry published new progress about Carbonylation. 69622-40-8 belongs to class indole-building-block, name is 2-(tert-Butyl)-5-chloro-1H-indole, and the molecular formula is C12H14ClN, Related Products of 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

Lu, Dong-Liang published the artcileAtroposelective Construction of Arylindoles by Chiral Phosphoric Acid-Catalyzed Cross-Coupling of Indoles and Quinones, Application of 2-(tert-Butyl)-5-chloro-1H-indole, the main research area is arylindole atroposelective synthesis phosphoric acid catalyzed coupling indole quinone.

Structurally novel atropisomeric arylindole frameworks have been successfully constructed through chiral phosphoric acid-catalyzed asym. cross-coupling of indoles and quinone derivatives in a precise regioselective manner. This approach features high convergence and functional group tolerance to efficiently deliver diverse heteroaryl atropisomers with excellent enantiocontrol. The dominant formation of axial chirality but not central chirality, as the major unmet challenge for this type of reactions, was conquered by the rational and accurate modulation of the electronic and steric effects on both coupling partners. Preliminary investigation demonstrated the practicality of such axially chiral arylindoles as chiral ligands in asym. catalysis.

Organic Letters published new progress about Atropisomers. 69622-40-8 belongs to class indole-building-block, name is 2-(tert-Butyl)-5-chloro-1H-indole, and the molecular formula is C12H14ClN, Application of 2-(tert-Butyl)-5-chloro-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

Qi, Liang-Wen published the artcileOrganocatalytic asymmetric arylation of indoles enabled by azo groups, Recommanded Product: 2-(tert-Butyl)-5-chloro-1H-indole, the main research area is organocatalytic asym arylation indole azo directing activating group; nucleophilic aromatic substitution asym organocatalytic; pyrroloindole preparation asym arylation azo directing activating group; arylindole preparation asym arylation azo directing activating group.

Arylation is a fundamental reaction that can be mostly fulfilled by electrophilic aromatic substitution and transition-metal-catalyzed aryl functionalization. Although the azo group has been used as a directing group for many transformations via transition-metal-catalyzed aryl carbon-hydrogen (C-H) bond activation, there remain significant unmet challenges in organocatalytic arylation. Here, we show that the azo group can effectively act as both a directing and activating group for organocatalytic asym. arylation of indoles via formal nucleophilic aromatic substitution of azobenzene derivatives Thus, a wide range of axially chiral arylindoles, e.g., I and II, have been achieved in good yields with excellent enantioselectivities by utilizing chiral phosphoric acid as catalyst. Furthermore, highly enantioenriched pyrroloindoles, e.g., III, bearing two contiguous quaternary chiral centers, have also been obtained via a cascade enantioselective formal nucleophilic aromatic substitution-cyclization process. This strategy should be useful in other related research fields and will open new avenues for organocatalytic asym. aryl functionalization.

Nature Chemistry published new progress about Arylation catalysts, stereoselective. 69622-40-8 belongs to class indole-building-block, name is 2-(tert-Butyl)-5-chloro-1H-indole, and the molecular formula is C12H14ClN, Recommanded Product: 2-(tert-Butyl)-5-chloro-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

Chen, Ye-Hui published the artcileOrganocatalytic Enantioselective Synthesis of Atropisomeric Aryl-p-Quinones: Platform Molecules for Diversity-Oriented Synthesis of Biaryldiols, Application of 2-(tert-Butyl)-5-chloro-1H-indole, the main research area is aryl quinone enantioselective preparation organocatalyst diversity oriented biaryldiol; atropisomerism; biaryls; chirality; organocatalysis; quinones.

Presented here is a class of novel axially chiral aryl-p-quinones as platform mols. for the preparation of non-C2 sym. biaryldiols. Two sets of aryl-p-quinone frameworks were synthesized with remarkable enantiocontrol by chiral phosphoric acid catalyzed enantioselective arylation of p-quinones by central-to-axial chirality conversion. These aryl-p-quinones were then used to access a wide spectrum of highly functionalized non-C2 sym. biaryldiols with excellent retention of the enantiopurity.

Angewandte Chemie, International Edition published new progress about Arylation catalysts, stereoselective (oxidative). 69622-40-8 belongs to class indole-building-block, name is 2-(tert-Butyl)-5-chloro-1H-indole, and the molecular formula is C12H14ClN, Application of 2-(tert-Butyl)-5-chloro-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

Qin, Jingyang published the artcileCatalytic Atroposelective Electrophilic Amination of Indoles, Name: 2-(tert-Butyl)-5-chloro-1H-indole, the main research area is sulfonyl arylaminoindole preparation enantioselective chemoselective anticancer activity DFT; Amination; Atroposelectivity; Conjugation; C−N Axis; Heterocycles.

The first catalytic atroposelective electrophilic amination of indoles I (R = 2-t-Bu, 4-Me, 5-Ph), which delivers functionalized atropochiral N-sulfonyl-3-arylaminoindoles II (R1 = Boc, (4-methylphenyl)sulfonyl, (1-naphthyl)sulfonyl, etc.) with excellent optical purity was reported. This reaction was furnished by 1,6-nucleophilic addition to p-quinone diimines III. Control experiments suggest an ionic mechanism that differs from the radical addition pathway commonly proposed for 1,6-addition to quinone III (R1 = (4-methylphenyl)sulfonyl). The origin of 1,6-addition selectivity was investigated through computational studies. Preliminary studies show that the obtained 3-aminoindoles atropisomers II exhibit anticancer activities. This method was valuable with respect to enlarging the toolbox for atropochiral amine derivatives II.

Angewandte Chemie, International Edition published new progress about Amination catalysts (chemo-, stereoselective). 69622-40-8 belongs to class indole-building-block, name is 2-(tert-Butyl)-5-chloro-1H-indole, and the molecular formula is C12H14ClN, Name: 2-(tert-Butyl)-5-chloro-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

Bellezza, Delia published the artcilePalladium-Catalyzed C-C Ring Closure in α-Chloromethylimines: Synthesis of 1H-Indoles, Name: 2-(tert-Butyl)-5-chloro-1H-indole, the main research area is chloromethylimine palladium phosphine ring closure catalyst; indole preparation.

The C-C ring closure of α-chloromethyl alkyl or aryl N-aryl imines catalyzed with 1 to 10 % Pd(OAc)2/P(p-tolyl)3 afford efficiently 2-aryl- and 2-alkyl-1H-indoles. The heterocyclization reaction involves the initial formation of [2-(arylimino)ethyl]palladium(II) chloride complexes with subsequent C-H activation of the aromatic amine ring. Readily or com. available α-chloromethyl-aryl or -alkyl ketones are used as the precursors. Functionalized indoles at the benzene ring are obtained when the imines are derived from substituted anilines.

European Journal of Organic Chemistry published new progress about Alkyl aryl ketones Role: RCT (Reactant), RACT (Reactant or Reagent) (Chloromethyl). 69622-40-8 belongs to class indole-building-block, name is 2-(tert-Butyl)-5-chloro-1H-indole, and the molecular formula is C12H14ClN, Name: 2-(tert-Butyl)-5-chloro-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

Zhu, Shuai published the artcileOrganocatalytic atroposelective construction of axially chiral arylquinones, Application In Synthesis of 69622-40-8, the main research area is axially chiral aryl quinone preparation organocatalytic atroposelective.

Herein, the atroposelective construction of axially chiral arylquinones I [R1 = H, CO2Me, CO2Bn, etc.; R2 = H, 7-Br, 6-OMe, etc.; R3 = H, 6-Me, 7-Ph, etc.; R4 = NH2, OH, NHPh, etc.] and II [X = Cl, Br, I; R5 = t-Bu, C(Me)2CH2CH3; R6 = H, 5-Me, 5-OMe, etc.] by a bifunctional chiral phosphoric acid-catalyzed asym. conjugate addition and central-to-axial chirality conversion was presented. With o-naphthoquinone as both the electrophile and the oxidant, three types of arylation counterparts, namely 2-naphthylamines, 2-naphthols and indoles, were utilized to assemble a series of atropisomeric scaffolds in good yields and excellent enantioselectivities. This approach not only expands the axially chiral library but also offered a route to a class of potential, chiral biomimetic catalysts.

Nature Communications published new progress about Aromatic amines Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 69622-40-8 belongs to class indole-building-block, name is 2-(tert-Butyl)-5-chloro-1H-indole, and the molecular formula is C12H14ClN, Application In Synthesis of 69622-40-8.

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

Ding, Wei-Yi published the artcileDFT-Guided Phosphoric-Acid-Catalyzed Atroposelective Arene Functionalization of Nitrosonaphthalene, Application of 2-(tert-Butyl)-5-chloro-1H-indole, the main research area is nitrosonaphthalene arene chiral phosphoric acid catalyst enantioselective functionalization.

This strategy enables efficient construction of atropisomeric indole-naphthalenes and indole-anilines with excellent stereocontrol. D. functional theory (DFT) calculations provided further insights into the origins of enantioselectivity and the reaction mechanisms. The successful application in the synthesis of NOBINs (2-amino-2′-hydroxy-1,1′-binaphthyl) extends the utility of this strategy.

Chem published new progress about C-H bond activation. 69622-40-8 belongs to class indole-building-block, name is 2-(tert-Butyl)-5-chloro-1H-indole, and the molecular formula is C12H14ClN, Application of 2-(tert-Butyl)-5-chloro-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