65417-22-3 | - Page 6 of 7 - Indole Building Blocks

Fabry, David C. et al. published their research in Accounts of Chemical Research in 2016 |CAS: 65417-22-3

The Article related to metal visible photocatalysis photoredox catalyst photocyclization olefination, Radiation Chemistry, Photochemistry, and Photographic and Other Reprographic Processes: Radiation Chemistry and Photochemistry and other aspects.Electric Literature of 65417-22-3

On September 20, 2016, Fabry, David C.; Rueping, Magnus published an article.Electric Literature of 65417-22-3 The title of the article was Merging Visible Light Photoredox Catalysis with Metal Catalyzed C-H Activations: On the Role of Oxygen and Superoxide Ions as Oxidants. And the article contained the following:

Visible light photoredox catalysis as a new alternative to conventionally applied regeneration/oxidation procedures was examined This account summarizes these recent advances in this expanding area and will highlight the new concept of merging distinct redox catalytic processes for C-H functionalizations through the application of visible light photoredox catalysis. Photoredox catalysis can be considered as catalytic electron-donating or -accepting processes, making use of visible-light absorbing homogeneous and heterogeneous metal-based catalysts, as well as organic dye sensitizers or polymers. As a consequence, photoredox catalysis is, in principle, an ideal tool for the recycling of any given metal catalyst via a coupled electron transfer (ET) process. Here we describe our first successful endeavors to address the above challenges by combining visible light photoredox catalysis with different ruthenium, rhodium, or palladium catalyzed C-H activations. Since only small amounts of the oxidant are generated and are immediately consumed in these transformations, side reactions of substrates or products can be avoided. Thus, usually oxidant-sensible substrates can be used, which makes these methods highly suitable for complex mol. structure syntheses. Moreover, mechanistic studies shed light on new reaction pathways, intermediates, and in situ generated species. The successful development of our dual catalysis concept, consisting of combined visible light photoredox catalysis and metal catalyzed C-H functionalization, provides many new opportunities for further explorations in the field of C-H functionalization. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Electric Literature of 65417-22-3

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

Moghadam, Faeze Kiani et al. published their research in Synlett in 2016 |CAS: 65417-22-3

The Article related to iodoaniline isothiocyanate copper catalyst cross coupling, aminobenzothiazole preparation, dicarbonyl compound iodoaniline copper catalyst cross coupling, indole preparation and other aspects.HPLC of Formula: 65417-22-3

On July 31, 2016, Moghadam, Faeze Kiani; Jarrah, Najmeh; Mashayekh-Salehi, Ali; Ghanbaripour, Rashid published an article.HPLC of Formula: 65417-22-3 The title of the article was A Synthesis of Benzothiazoles and Indoles by Direct C(sp2)-I Activation Catalyzed by Copper(II) on Silica-Coated Magnetite Nanoparticles. And the article contained the following:

N-Substituted 2-amino-1,3-benzothiazoles and 2,3-disubstituted indoles were prepared by C-S and C-C cross-coupling reactions of 2-iodoanilines with isothiocyanates or 1,3-dicarbonyl compounds, resp., in the presence of magnetic nanoparticles functionalized with a copper(II)-Schiff base complex as an efficient and reusable catalyst. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).HPLC of Formula: 65417-22-3

Wuertz, Sebastian et al. published their research in Angewandte Chemie, International Edition in 2008 |CAS: 65417-22-3

The Article related to aniline derivative acetoacetate condensation, enaminone aryl derivative preparation palladium catalyst oxidative cyclization, indole carboxylate derivative preparation kinetics and other aspects.Related Products of 65417-22-3

Wuertz, Sebastian; Rakshit, Souvik; Neumann, Julia J.; Droege, Thomas; Glorius, Frank published an article in 2008, the title of the article was Palladium-catalyzed oxidative cyclization of N-aryl enamines: from anilines to indoles.Related Products of 65417-22-3 And the article contains the following content:

The special advantage of the title reaction to form substituted indoles lies within the broad scope of the transformation: a multitude of N-aryl enaminones, e.g., I, can be prepared readily in one step from com. available anilines. Furthermore, anilines can be converted directly in a one-pot process into the indole products, e.g., II. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Related Products of 65417-22-3

Zoller, Jochen et al. published their research in Angewandte Chemie, International Edition in 2014 |CAS: 65417-22-3

The Article related to indole carboxylate preparation, enamine intramol oxidative cyclization palladium photoredox catalysis visible light, ch functionalization, heck reaction, photocatalysis, superoxide and other aspects.Related Products of 65417-22-3

Zoller, Jochen; Fabry, David C.; Ronge, Meria A.; Rueping, Magnus published an article in 2014, the title of the article was Synthesis of Indoles Using Visible Light: Photoredox Catalysis for Palladium-Catalyzed C-H Activation.Related Products of 65417-22-3 And the article contains the following content:

A combined palladium- and photoredox-catalyzed C-H olefination enables the synthesis of indoles. By using visible light, the direct C-H activation of aromatic enamines I (R1 = H, 4-PhO, 4-Cl, 2-F, 3,5-Me2, etc.; R2 = Me, Ph; R3 = Me, Et, t-Bu, PhCH2) can be achieved, and a variety of indoles II can be obtained in good yields under mild reaction conditions. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Related Products of 65417-22-3

Yamazaki, Kazuo et al. published their research in Journal of Organic Chemistry in 2003 |CAS: 65417-22-3

The Article related to indolecarboxylate solid phase preparation, fused pyridine pyridone solid phase preparation, solid phase preparation indolecarboxylate palladium rhodium catalyzed cyclization reaction and other aspects.Name: Methyl 2-methyl-1H-indole-3-carboxylate

On July 25, 2003, Yamazaki, Kazuo; Nakamura, Yosuke; Kondo, Yoshinori published an article.Name: Methyl 2-methyl-1H-indole-3-carboxylate The title of the article was Solid-Phase Synthesis of Indolecarboxylates Using Palladium-Catalyzed Reactions. And the article contained the following:

Indolecarboxylates are prepared on solid support using palladium-catalyzed reactions as the key steps. Supported β-amino-α,β-unsaturated esters are prepared either by attachment of tert-Bu acetoacetate to a resin followed by condensation with 2-haloanilines or by condensation of acryloyl chloride with a resin followed by Wacker-type oxidation of 2-haloanilines with the resin-bound acrylate in the presence of palladium catalysts. Supported α-amino-α,β-unsaturated esters are prepared by coupling of diethylphosphonoacetic acid to a resin followed by diazo transfer, rhodium-catalyzed insertion of 2-haloanilines, and base-mediated olefination with aldehydes. Palladium-catalyzed cyclization reactions of the α- or β-amino-α,β-unsaturated esters followed by cleavage of the resin-bound esters with sodium methoxide yields indolecarboxylates in moderate yields and purities. Rhodium-catalyzed insertion reactions of aminophenyl ketones and aldehydes with α-diazophosphonate esters followed by base-mediated cyclocondensation and cleavage from the resin with sodium methoxide also yields indolecarboxylates in low to moderate yields and purities. Resin-bound β-(halophenyl)-α-aminoacrylates are prepared either by attachment of an aminoacrylate to a resin followed by Heck arylation with an aryl halide or by rhodium-catalyzed insertion of an amine into a resin-bound α-diazophosphonate followed by olefination with halobenzaldehydes. Palladium-catalyzed cyclization of the resin-bound β-(halophenyl)-α-aminoacrylates followed by resin cleavage yields indolecarboxylates in 43-98% yields. A shorter version of this synthesis is also employed; palladium-catalyzed Heck reaction of 1,2-dihaloarenes with resin-bound acetylaminoacrylic acid followed by resin cleavage yields indolecarboxylates directly in 31-99% yields. Formylbromoarenes and -heteroarenes and methoxycarbonylarenes and -heteroarenes such as Me 2-bromobenzoate undergo palladium-catalyzed coupling with resin-bound acetylaminoacrylic acid followed by cyclization to yield fused pyridines and pyridones such as Me 1,2-dihydro-1-oxo-3-isoquinolinecarboxylate in 52-62% yields. 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

Li, Yunyun et al. published their research in Angewandte Chemie, International Edition in 2016 |CAS: 65417-22-3

The Article related to diazoketoester imidamide ruthenium activation annulation catalyst, nh indole preparation, diazomalonate imidamide ruthenium activation annulation catalyst, indole 3h preparation, c−h activation, diazo compounds, indoles, ruthenium, transition-metal catalysis and other aspects.Electric Literature of 65417-22-3

Li, Yunyun; Qi, Zisong; Wang, He; Yang, Xifa; Li, Xingwei published an article in 2016, the title of the article was Ruthenium(II)-Catalyzed C-H Activation of Imidamides and Divergent Couplings with Diazo Compounds: Substrate-Controlled Synthesis of Indoles and 3H-Indoles.Electric Literature of 65417-22-3 And the article contains the following content:

Indoles are an important structural motif that is commonly found in biol. active mols. In this work, conditions for divergent couplings between imidamides and acceptor-acceptor diazo compounds were developed that afforded NH indoles I (R = Et, Me, tbu, Bn, Ac; R1 = H, 5-Me, 5-Br, 4-F, 6-Cl, etc) and 3H-indoles II (R = Et, Me, tBu, Bn, ipr, allyl; R1 = H, 5-Cl, 5-tbu, 5-CN, 5,6-diCl, etc) under ruthenium catalysis. The coupling of α-diazoketoesters afforded NH indoles by cleavage of the C(N2)-C(acyl) bond whereas α-diazomalonates gave 3H-indoles by C-N bond cleavage. This reaction constitutes the first intermol. coupling of diazo substrates with arenes by ruthenium-catalyzed C-H activation. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Electric Literature of 65417-22-3

Wang, Guangyong et al. published their patent in 2016 |CAS: 65417-22-3

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

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

Fabry, David et al. published their research in Organic Chemistry Frontiers |CAS: 65417-22-3

The Article related to pyridinyloxyphenylacrylate carbamoylphenylacrylate preparation diastereoselective, diaryl ether acrylate ortho olefination semiconductor photocatalyst, weinreb amide acrylate ortho olefination semiconductor photocatalyst, indole preparation semiconductor photoredox catalyst, enamine cyclization semiconductor photocatalyst palladium catalyst and other aspects.Category: indole-building-block

Fabry, David; Zoller, Jochen; Rueping, Magnus published an article in , the title of the article was Semiconductors as Heterogeneous Visible Light Photoredox Catalysts in Combined Dual Metal Catalyzed C-H Functionalizations.Category: indole-building-block And the article contains the following content:

The application of heterogeneous semiconductors as visible-light photoredox catalysts for transition metal-catalyzed C-H olefination reactions of diaryl ethers/Weinreb amides with acrylates to afford aryl-acrylates I [R1 = 3-OMe, 3-OMe-5-(prop-1-en-1-yl), R2 = Me, Et, Bu, CH2C2F5] and Bu (E)-3-(carbamoylphenyl)acrylates II [R3 = H, 5-Me, 5-OMe, 5-tert-Bu, R5 = Me, OMe, R6 = Me, R5R6 = piperidin-1-yl, morpholin-4-yl] is reported. Also, the application of heterogeneous semiconductors along with palladium catalyzed enamine cyclization provided substituted indoles III [R7 = H, 5-OMe, 7-Me, etc., R8 = Me, tert-Bu]. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Category: indole-building-block

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The iron(II)-catalyzed domino isomerization of 3-alkyl/aryl-4-arylisoxazoles provides a selective access to a wide range of structurally diverse highly substituted indole-3-carboxylates. The operational simplicity, high atom efficiency, and the use of stable starting materials and an inexpensive and low-toxicity catalyst are some of the attractive features of this tandem double ring-opening-ring-closure strategy.

Reference：
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

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An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated ?CBr3 radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes to synthesize the desired carboxylated product in moderate-to-good yields. The reaction proceeding through a single electron transfer pathway was established by a control experiment, and a butylated hydroxytoluene-trapped aryl radical cation intermediate in high-resolution mass spectrometry was identified.