October 2022 - Page 20 of 72 - Indole Building Blocks

Rather, Rafiq A.’s team published research in Tetrahedron in 2021 | 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: 399-52-0

Rather, Rafiq A.; Ara, Tabassum published their research in Tetrahedron in 2021. The article was titled 《Copper catalyzed synthesis of 3-((arylethynyl)selanyl)-1H-indoles via selenium insertion reaction by using elemental selenium》.Recommanded Product: 399-52-0 The article contains the following contents:

Herein, an efficient and simple strategy for the synthesis of biol. relevant 3-((arylethynyl)selanyl)-1H-indoles I (R = H, 2-Cl, 3-Me, 4-OCF3, etc.; R1 = H, Me, OMe, F, etc.; R2 = H, Br) have been disclosed. The reactions were carried out in presence of a catalytic amount of copper (I) bromide. The selenide adduct tolerates all types of substrates used. Furthermore, all the products I were obtained in good to excellent yields. Unique coupling, multicomponent, one-pot access served a useful output in organic synthesis design. In the experimental materials used by the author, we found 5-Fluoro-1H-indole(cas: 399-52-0Recommanded Product: 399-52-0)

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

Cao, Min’s team published research in Tetrahedron Letters in 2019 | 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).Electric Literature of C8H6FN

Electric Literature of C8H6FNIn 2019 ,《Cross-dehydrogenative coupling of secondary benzylic ethers with indoles and pyrroles》 appeared in Tetrahedron Letters. The author of the article were Cao, Min; Mao, Ying; Huang, Jiancheng; Ma, Yudao; Liu, Lei. The article conveys some information:

The first cross-dehydrogenative coupling of secondary benzylic ethers with indoles and pyrroles for tertiary ether construction was described. A broad range of α-aryl substituted isochromans react with a variety of electronically varied indoles and pyrroles smoothly under mild metal-free conditions in high efficiency. In addition, the catalytic asym. variant was preliminarily explored and corresponding tertiary ether was obtained in 69% ee.5-Fluoro-1H-indole(cas: 399-52-0Electric Literature of C8H6FN) was used in this study.

Ault, James R.’s team published research in HortScience in 1996 | 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.COA of Formula: C12H12KNO2

Ault, James R. published their research in HortScience on December 31 ,1996. The article was titled 《In vitro rooting and greenhouse acclimatization of Veltheimia bracteata and V. capensis shoots》.COA of Formula: C12H12KNO2 The article contains the following contents:

Shoot initiation and multiplication were obtained in vitro from immature flower bud and leaf explants of Veltheimia bracteata Bak. ‘Lemon Flame’ and from leaf explants of V. bracteata ‘Rosalba’ cultured on a Murashige and Skoog (MS) medium supplemented with sucrose at 30 g·L-1, and either 8.87 μM BA plus 0.54 μM NAA or 8.87 μM BA plus 5.40 μM NAA. Shoot initiation and multiplication was obtained from a single leaf explant of Veltheimia capensis (L.) DC. on MS medium with 8.87 μM BA plus 0.54 μM NAA. Shoots of the three genotypes rooted on subculture to medium with 0.0, 4.14, or 8.29 μM K-IBA or 0.0, 4.46, or 8.92 μM K-NAA. Maximal rooting was 98% for V. bracteata ‘Lemon Flame’, 95% for V. bracteata ‘Rosalba’, and 98% for V. capensis, from medium with 4.46 μM K-NAA. Rooted shoots were acclimatized for 3 to 4 wk. Overall survival percentage was 69% for V. bracteata ‘Lemon Flame’, 65% for V. bracteata ‘Rosalba’, and 83% for V. capensis.Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3COA of Formula: C12H12KNO2) was used in this study.

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

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.

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

《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)