21/10/2022 - Page 5 of 5 - Indole Building Blocks

Ibanez, Ignacio’s team published research in ACS Catalysis in 2019 | CAS: 399-52-0

5-Fluoro-1H-indole(cas: 399-52-0) is a member of aromaticfluorinated building blocks. Fluorine-containing aromatics have been incorporated into crop-protection chemicals (herbicides, insecticides, fungicides). Liquid crystals, positron emission tomography, and imaging systems represent new areas where fluoroaromatics and fluoroheterocyclics have gained attention.Recommanded Product: 5-Fluoro-1H-indole

The author of 《Enantioselective Friedel-Crafts Alkylation Reaction of Indoles with α-Trifluoromethylated β-Nitrostyrenes Catalyzed by Chiral BINOL Metal Phosphate》 were Ibanez, Ignacio; Kaneko, Mio; Kamei, Yuto; Tsutsumi, Ryosuke; Yamanaka, Masahiro; Akiyama, Takahiko. And the article was published in ACS Catalysis in 2019. Recommanded Product: 5-Fluoro-1H-indole The author mentioned the following in the article:

An efficient enantioselective Friedel-Crafts alkylation reaction of indoles with α-CF3-substituted β-nitrostyrenes is disclosed. The key to success is the use of a chiral calcium BINOL bis(phosphate) complex as a Lewis acid catalyst. The reaction gives access to a wide variety of optically active indoles bearing trifluoromethylated all-carbon quaternary stereocenter (up to 20 examples) in high yields (up to 99%) with excellent enantioselectivities (up to 98%) under mild reaction conditions. Nonactivated α-alkyl-β-nitrostyrenes also participated in the Friedel-Crafts alkylation reaction successfully.5-Fluoro-1H-indole(cas: 399-52-0Recommanded Product: 5-Fluoro-1H-indole) was used in this study.

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

Ban, Yong-Liang’s team published research in ACS Catalysis in 2021 | CAS: 399-52-0

Ban, Yong-Liang; You, Long; Wang, Tao; Wu, Li-Zhu; Liu, Qiang published an article in 2021. The article was titled 《Metallaphotoredox Dearomatization of Indoles by a Benzamide-Empowered [4 + 2] Annulation: Facile Access to Indolo[2,3-c]isoquinolin-5-ones》, and you may find the article in ACS Catalysis.Name: 5-Fluoro-1H-indole The information in the text is summarized as follows:

Herein, a metallaphotoredox catalysis protocol enabling the efficient dearomatization of indoles I (R = quinolin-8-yl, (tert-butoxy)carbonyl; R1 = H, Me, OMe, hydroxymethyl, (acetyloxy)methyl; R2 = H, F, 2-oxocyclohexyl, morpholin-4-yl, etc.; R3 = H, Me; R4 = H, Me) utilizing readily available N-quinolyl benzamides II (R5 = Ph, thiophen-2-yl, 2H-1,3-benzodioxol-5-yl, etc.) under environmentally benign reaction conditions was reported. This reaction allows regioselective C-2 and C-3 dual functionalization of indoles and provides a mild, straightforward, and high atom- and step-economical approach to produce a diverse array of indolo[2,3-c]isoquinolin-5-ones e.g., III by merging cobalt catalysis with photocatalysis. The practicality and effectiveness of this synergistic protocol were illustrated by a gram-scale experiment Preliminary mechanistic studies indicate that a single-electron transfer process is involved during the catalytic cycle. In addition, a catalytically competent organometallic Co(bzac)3 has been identified through X-ray crystallog., 1H NMR, 13C NMR, and ESI-HRMS. In addition to this study using 5-Fluoro-1H-indole, there are many other studies that have used 5-Fluoro-1H-indole(cas: 399-52-0Name: 5-Fluoro-1H-indole) was used in this study.

Han, Zhi-Peng’s team published research in Green Chemistry in 2021 | CAS: 399-52-0

Han, Zhi-Peng; Xu, Meng-Meng; Zhang, Rui-Ying; Xu, Xiao-Ping; Ji, Shun-Jun published an article in 2021. The article was titled 《Rh(III)-Catalyzed C(sp2)-H functionalization/cyclization cascade of N-carboxamide indole and iodonium reagents for access to indoloquinazolinone derivatives》, and you may find the article in Green Chemistry.Product Details of 399-52-0 The information in the text is summarized as follows:

A rhodium-catalyzed synthesis of indoloquinazolinones, e.g., I, from a hypervalent iodonium reagents and N-carboxamide indoles was developed. The protocol featured broad functional group tolerance, mild conditions, and excellent yields. The target products were obtained simply by filtration, without tedious column chromatog. Notably, the noble metal catalyst system could be recycled effectively at least ten times. The strategy may be amenable to industrial production5-Fluoro-1H-indole(cas: 399-52-0Product Details of 399-52-0) was used in this study.

Zhu, Wen-Run’s team published research in Chemical Science in 2022 | CAS: 399-52-0

In 2022,Zhu, Wen-Run; Su, Qiong; Deng, Xiao-Yi; Liu, Jia-Sheng; Zhong, Tao; Meng, Shan-Shui; Yi, Ji-Tao; Weng, Jiang; Lu, Gui published an article in Chemical Science. The title of the article was 《Organocatalytic enantioselective SN1-type dehydrative nucleophilic substitution: access to bis(indolyl)methanes bearing quaternary carbon stereocenters》.Electric Literature of C8H6FN The author mentioned the following in the article:

A highly general and straightforward approach to access chiral bis(indolyl)methanes (BIMs) bearing quaternary stereocenters was realized via enantioconvergent dehydrative nucleophilic substitution. A broad range of 3,3′-, 3,2′- and 3,1′-BIMs were obtained under mild conditions with excellent efficiency and enantioselectivity (80 examples, up to 98% yield and >99 : 1 er). By utilizing racemic 3-indolyl tertiary alcs. as precursors of alkyl electrophiles and indoles as C-H nucleophiles, this organocatalytic strategy avoids pre-activation of substrates and produces water as the only byproduct. Mechanistic studies suggest a formal SN1-type pathway enabled by chiral phosphoric acid catalysis. The practicability of the obtained enantioenriched BIMs was further demonstrated by versatile transformation and high antimicrobial activities. The experimental part of the paper was very detailed, including the reaction process of 5-Fluoro-1H-indole(cas: 399-52-0Electric Literature of C8H6FN)

Keeley, Kathryn’s team published research in HortScience in 2003 | CAS: 60096-23-3

Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3) is auxin-family plant hormone, and is thought to be a precursor of indole-3-acetic acid (IAA) the most abundant and the basic auxin natively occurring and functioning in plants. IAA generates the majority of auxin effects in intact plants, and is the most potent native auxin.Application of 60096-23-3

《Increased rooting of ‘Norton’ grape cuttings using auxins and gibberellin biosynthesis inhibitors》 was written by Keeley, Kathryn; Preece, John E.; Taylor, Bradley H.. Application of 60096-23-3 And the article was included in HortScience on April 30 ,2003. The article conveys some information:

Hardwood and softwood cuttings of Vitis aestivalis Michx. ‘Norton’ were rooted under intermittent mist in a series of experiments using cuttings collected from two local vineyards. Hardwood cuttings treated in late Mar. responded in a similar manner to KIBA and KNAA. Although there was little increase in the percentage rooting above 22.29 mM KIBA or 20.72 mM KNAA (5000 mg·L-1 of either auxin), root number (but not root length) increased linearly on cuttings treated with up to 44.58 mM KIBA or 41.44 mM KNAA (10000 mg·L-1 auxin). Cuttings treated with 10000 mg·L-1 auxin produced up to 4 times more roots than the nontreated controls. The gibberellin biosynthesis inhibitors CCC and PAC had little effect on either hardwood cuttings or softwood cuttings that were harvested, treated and placed in the propagation bench in June. However, when softwood cuttings were collected in August, the most roots were found on cuttings treated with 50.6 mM CCC or 0.85 μm PAC. Although all hardwood cuttings were collected at the same time and stored under refrigerated conditions, rooting percentage increased as storage time increased, especially on the nontreated control cuttings. When the cuttings were stored for the longest time (six weeks), KIBA no longer caused more roots per cutting. In the part of experimental materials, we found many familiar compounds, such as Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3Application of 60096-23-3)

King, Andrew R.’s team published research in HortScience in 2011 | CAS: 60096-23-3

Category: indole-building-blockOn October 31, 2011 ,《Substrates, wounding, and growth regulator concentrations alter adventitious rooting of baldcypress cuttings》 appeared in HortScience. The author of the article were King, Andrew R.; Arnold, Michael A.; Welsh, Douglas F.; Watson, W. Todd. The article conveys some information:

In previous studies, baldcypress [Taxodium distichum (L.) Rich.] clones were selected for tolerance to high pH soils, drought and salt exposures, and ornamental characteristics. The objective of the current research was to determine the treatment combinations that yielded optimum root quantity (percentage) and rooted cutting quality (root number, length, dry mass, and shoot dry mass) on vegetative cuttings for a representative clone. Cuttings were treated with factorial combinations of one of four potassium salt of indole-3-butyric acid (K-IBA) concentrations 40, 5000, 10,000, 15,000 mg·L-1 (0, 20.72, 41.44, 62.16 mM, resp.), wounded or not wounded (1-cm long basal incision), and rooted in one of three substrates (100% perlite, 100% peatmoss, or 50% perlite:50% peatmoss). Data indicated a tradeoff between potential rooting quantity and root quality measurements in response to different substrates. Although rooting percentages were affected by substrates only at P ≤ 0.10 (53% in 100% perlite vs. 36% in 100% peatmoss), there were highly significant (P ≤ 0.0001) differences in rooted cutting potential among substrates as measured by the percentage of cuttings with basal callus. Cuttings placed in 100% perlite callused at 85%, whereas cuttings placed in 100% peatmoss callused at ≈53%. The 100% peatmoss treatment, however, yielded cuttings with significantly greater root quality for all measurements, except root number per cutting. Wounding cuttings proved to have deleterious effects on root quality measurements. Total root length was ≈14.5 cm for non-wounded cuttings and ≈10.8 cm for wounded cuttings. Increasing K-IBA concentrations did not significantly (P ≤ 0.05) affect rooting or callus percentages but did significantly affect root dry mass, total root length, and average root length per cutting. Total root length increased from 10.8 cm at 0 mg·L-1 K-IBA to 16 cm at 15,000 mg·L-1 K-IBA. Mean root number per cutting increased from ≈1.6 with wounded cuttings planted in 100% peatmoss to ≈3.1 with non-wounded cuttings planted in 100% perlite. Results suggested that high-quality softwood baldcypress cuttings should not be wounded, should be treated with 15,000 mg·L-1 K-IBA, and grown in a substrate with intermediate water-holding capacity to achieve an acceptable balance between rooting percentage and rooted cutting quality objectives. In the experiment, the researchers used many compounds, for example, Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3Category: indole-building-block)

Levitre, Guillaume’s team published research in ChemCatChem in 2019 | CAS: 399-52-0

In 2019,ChemCatChem included an article by Levitre, Guillaume; Audubert, Clement; Dumoulin, Audrey; Goual, Nawel; Retailleau, Pascal; Moreau, Xavier; Masson, Geraldine. Application of 399-52-0. The article was titled 《Combining Organocatalysis and Photoredox Catalysis: An Asymmetric Synthesis of Chiral β-Amino α-Substituted Tryptamines》. The information in the text is summarized as follows:

A stereoselective synthesis of functionalized β-amino α-substituted tryptamines I [R1 = Me, cyclopropyl, (CH2)3OTBDPS, etc.; R2 = H, 7-I, 5-MeO, etc.] was achieved by a sequential asym. organocatalytic three-component electrophilic amination and photocatalyzed Friedel-Crafts reaction of indoles with moderate to high diastereoselectivities (up to >99 : 1 dr) and excellent enantioselectivities (up to >99 % ee). It was also demonstrated that the β-amino α-substituted tryptamines could be successfully engaged in a further catalytic step, furnishing various α, β-substituted tryptamines II [R3 = allyl, 2-methoxythienyl, benzofuran-3-yl, etc.] without erosion of enantioselectivity and with complete diastereoselectivity. In the experimental materials used by the author, we found 5-Fluoro-1H-indole(cas: 399-52-0Application of 399-52-0)

Dong, Chun-Lin’s team published research in Organic Letters in 2020 | CAS: 399-52-0

《Merging Visible Light Photocatalysis and L-/D-Proline Catalysis: Direct Asymmetric Oxidative Dearomatization of 2-Arylindoles To Access C2-Quaternary Indolin-3-ones》 was written by Dong, Chun-Lin; Ding, Xuan; Huang, Lan-Qian; He, Yan-Hong; Guan, Zhi. Computed Properties of C8H6FN And the article was included in Organic Letters in 2020. The article conveys some information:

A mild and effective method for asym. synthesis of C2-quaternary indolin-3-ones directly from 2-arylindoles by combining visible light photocatalysis and organocatalysis is described. In this reaction, 2-substituted indoles undergo photocatalyzed oxidative dearomatization, followed by an organocatalyzed asym. Mannich reaction with ketones or aldehydes. Products with opposite configurations are easily obtained in satisfactory yields with excellent enantio- and diastereoselectivity by employing readily available L- and D-proline as chiral organocatalysts. In the part of experimental materials, we found many familiar compounds, such as 5-Fluoro-1H-indole(cas: 399-52-0Computed Properties of C8H6FN)

Wen, Zhen-Kang’s team published research in Organic Letters in 2020 | CAS: 399-52-0

5-Fluoro-1H-indole(cas: 399-52-0) is a member of aromaticfluorinated building blocks. Depending on which substituents are present, fluoroaromatic intermediates can be converted into fluorinated or fluorine-free commercial end products.Fluorine-containing aromatics have been incorporated into drugs (hypnotics, tranquilizers, antiinflammatory agents, analgesics, antibacterials).Recommanded Product: 399-52-0

《Palladium-Catalyzed Regioselective Coupling Cyclohexenone into Indoles: Atom-Economic Synthesis of β-Indolyl Cyclohexenones and Derivatization Applications》 was written by Wen, Zhen-Kang; Wu, Xiao-Xue; Bao, Wen-Kai; Xiao, Jing-Jing; Chao, Jian-Bin. Recommanded Product: 399-52-0 And the article was included in Organic Letters in 2020. The article conveys some information:

Herein, we report a palladium-catalyzed dehydrogenative cross-coupling of indoles with cyclic enones to give β-indolyl cyclic enones under mild and neutral reaction conditions. The key to the success is to explore a mild condition, which ensures the indole C-H activation and subsequent syn β-hydride elimination through rapid enolization isomerization of Pd(II)-enolate while suppressing other undesired side reactions. Synthetic utility has also been demonstrated in the flexible transformation of the coupling products to meta-phenols and benzo[a]carbazoles. After reading the article, we found that the author used 5-Fluoro-1H-indole(cas: 399-52-0Recommanded Product: 399-52-0)