20/10/2022 - Indole Building Blocks

Wu, Cheng-Juan’s team published research in Organic Letters 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.Product Details of 399-52-0

Wu, Cheng-Juan; Cao, Wen-Xiao; Chen, Bin; Tung, Chen-Ho; Wu, Li-Zhu published their research in Organic Letters in 2021. The article was titled 《Tandem [2 + 2] Cycloaddition/Rearrangement toward Carbazoles by Visible-Light Photocatalysis》.Product Details of 399-52-0 The article contains the following contents:

Reported herein is the first example of the synthesis of carbazoles via oxidative cyclization of 3-alkenylindoles with styrenes under visible light. The irradiation of a catalytic amount of [Ir(dtbbpy)(ppy)2][PF6] as the photocatalyst enables various 3-alkenylindoles and styrenes to undergo tandem [2 + 2] cycloaddition/rearrangement, thereby leading to carbazole derivatives in good to excellent yields under aerobic conditions. Mechanistic studies reveal that photoinduced energy transfer followed by electron transfer is responsible for the tandem reaction. In the experimental materials used by the author, we found 5-Fluoro-1H-indole(cas: 399-52-0Product Details of 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

Jiang, Zhidong’s team published research in Organic Letters in 2021 | CAS: 399-52-0

Jiang, Zhidong; Zhou, Jianhui; Zhu, Haoran; Liu, Hong; Zhou, Yu published their research in Organic Letters in 2021. The article was titled 《Rh(III)-Catalyzed [5+1] Annulation of Indole-enaminones with Diazo Compounds To Form Highly Functionalized Carbazoles》.Category: indole-building-block The article contains the following contents:

A novel Rh(III)-catalyzed C-H activation/annulation cascade of indole-enaminones with diazo compounds was reported to construct diversely functionalized carbazole frameworks. The most notable characteristic was that, this transformation smoothly furnished a novel [5+1] cyclization product with good to excellent yields (up to 95%), accompanied by the thorough removal of acetyl and N,N-di-Me groups of two substrates from the target products, rather than the normally expected [4+2] cyclization products. The experimental part of the paper was very detailed, including the reaction process of 5-Fluoro-1H-indole(cas: 399-52-0Category: indole-building-block)

Anjitha, T.’s team published research in Polymer Composites in 2019 | CAS: 120-72-9

1H-Indole(cas: 120-72-9) belongs to indole. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Recommanded Product: 120-72-9

Recommanded Product: 120-72-9In 2019 ,《Zinc ferrite @ polyindole nanocomposites: synthesis, characterization and gas sensing applications》 appeared in Polymer Composites. The author of the article were Anjitha, T.; Anilkumar, T.; Mathew, G.; Ramesan, M. T.. The article conveys some information:

This research work deals with the synthesis and characterization of polyindole (PIN)/zinc ferrite (ZnFe2O4) nanocomposite. In situ polymerization of indole with different contents of ZnFe2O4 nanoparticles has been employed in the work. Structural, morphol., thermal, gas sensing and elec. properties of the prepared composites have been evaluated. The shifting of peaks in the fourier transform IR and UV-visible spectrum has been found to reveal the interaction of ZnFe2O4 nanoparticles with the PIN matrix. Crystalline nature of the nanocomposites resulting from the presence of crystalline (ZnFe2O4) has been revealed by X-ray diffraction studies (XRD). Scanning electron microscope and high-resolution transmission electron microscopy images revealed the uniform dispersion of nanoparticles at lower loading while at 15 % there are particle agglomerations. Improved thermal stability with the addition of (ZnFe2O4) nanoparticles in PIN has been confirmed by thermogravimetry while the enhancement in glass transition temperature of the nanocomposite with respect to pure polymer has been confirmed by differential scanning calorimetry. The addition of nanoparticles greatly enhanced the a.c. and d.c. conductivity, the dielec. constant and dielec. loss of PIN. The composite with 7 % shows the maximum properties. The fabricated composites showed excellent sensitivity and fast response to ammonia gas at room temperature Thus the study reveals that the PIN/ZnFe2O4 nanocomposites can be considered as a potential candidate for the applications in sensors and nanoelectronic devices. The experimental part of the paper was very detailed, including the reaction process of 1H-Indole(cas: 120-72-9Recommanded Product: 120-72-9)

Ghosh, B.’s team published research in Biologia Plantarum in 1994 | 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

《Micropropagation of Asparagus cooperi as affected by growth regulators》 was published in Biologia Plantarum in 1994. These research results belong to Ghosh, B.; Sen, S.. Application of 60096-23-3 The article mentions the following:

For clonal propagation of Asparagus cooperi, shoot tips and node explants of 7, 20 and 35 d old spears from the region within 10 cm and below 25 cm from the apex were cultured in modified Murashige and Skoog’s (1962) medium containing 6-benzylaminopurine (BAP). The required concentration of BAP varied in explants of different ages and types. In shoot tip culture, the rate of shoot multiplication was higher after 40 d than 60 d of culture. The maximum number (62 – 65) of shoots were obtained from shoot tip explants of 20 d old spears in the medium containing 2.0 mg dm-3 of BAP, 80 mg dm-3 of adenine and 0.02 mg dm-3 of α-naphthalene acetic acid after 60 d of culture. From node cultures, high number of shoots were obtained after 30 d. Pretreatment with BAP in liquid medium for 48 h was effective for semirejuvenescence. The individual shoots produced roots in presence of indole-3-butyric acid and also in potassium salt of indole-3-butyric acid, the later being more effective. All regenerants were cytol. stable. The results came from multiple reactions, including the reaction of Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3Application of 60096-23-3)

Tatai, Janos’s team published research in Organic Letters in 2007 | CAS: 99409-32-2

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.Computed Properties of C22H25NO9SThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.

Computed Properties of C22H25NO9SOn October 25, 2007 ,《A New, Powerful Glycosylation Method: Activation of Thioglycosides with Dimethyl Disulfide-Triflic Anhydride》 was published in Organic Letters. The article was written by Tatai, Janos; Fuegedi, Peter. The article contains the following contents:

Di-Me disulfide reacts with triflic anhydride to provide a highly reactive electrophile. Various thioglycosides, differing in their thio aglycons, carbohydrate units, and protecting group pattern, were activated with Me2S2-Tf2O in the presence of different glycosyl acceptors with both on primary and secondary hydroxyls. The reactions proceeded at low temperatures within a short time, affording disaccharides, e.g. I, in high yields. Armed and disarmed glycosyl donors were activated equally efficiently. In the part of experimental materials, we found many familiar compounds, such as Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2Computed Properties of C22H25NO9S)

Couvillon, G. A.’s team published research in HortScience in 1980 | CAS: 60096-23-3

Couvillon, G. A.; Erez, A. published their research in HortScience on February 29 ,1980. The article was titled 《Rooting, survival, and development of several peach cultivars propagated from semihardwood cuttings》.SDS of cas: 60096-23-3 The article contains the following contents:

Semi-hardwood cuttings of 13 cultivars of peach (Prunus persica) collected in 2 locations were successfully rooted and transplanted to the field. Rooting was increased by IBA K salt [60096-23-3] (1500-3500 mg/L). The results came from multiple reactions, including the reaction of Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3SDS of cas: 60096-23-3)

Gilbert, Eric J.’s team published research in Tetrahedron in 1997 | CAS: 74339-45-0

Methyl 2-(5-chloro-1H-indol-3-yl)acetate(cas: 74339-45-0) is a member of organic chlorides. Organic chlorides are compounds containing a carbon-chlorine bond, which are widely used in the oil field as a wax dissolver. They are generally not present in crude oils and are typically the result of additives, cleaning solutions or chemicals used for oil recovery.Computed Properties of C11H10ClNO2

Gilbert, Eric J.; Ziller, Joseph W.; Van Vranken, David L. published their research in Tetrahedron on December 1 ,1997. The article was titled 《Cyclizations of unsymmetrical bis-1,2-(3-indolyl)ethanes: synthesis of (-)-tjipanazole F1》.Computed Properties of C11H10ClNO2 The article contains the following contents:

The inter- and intramol. dimerization of 3-substituted indoles was studied. The rate and extent of dimerization depends on the indole substituents. The intramol. dimerization of unsym. bis-1,2-(3-indolyl)ethanes could be controlled using either thermodn. reaction conditions (neat trifluoroacetic acid) or kinetic conditions (2 equiv acid/chloroform). This control of regiochem. has been applied to an efficient synthesis of (-)-tjipanazole F1. In addition to this study using Methyl 2-(5-chloro-1H-indol-3-yl)acetate, there are many other studies that have used Methyl 2-(5-chloro-1H-indol-3-yl)acetate(cas: 74339-45-0Computed Properties of C11H10ClNO2) was used in this study.

Tabata, Mutsuko’s team published research in Heterocycles in 2020 | CAS: 74339-45-0

In 2020,Heterocycles included an article by Tabata, Mutsuko; Oshikiri, Naoki; Hasegawa, Masakazu; Satoh, Keiichi; Fukui, Yoshikazu; Nagahama, Yoshiyuki; Morikawa, Harunobu; Yamada, Fumio; Somei, Masanori. Quality Control of Methyl 2-(5-chloro-1H-indol-3-yl)acetate. The article was titled 《1-hydroxyindoles: production of feruloylserotonin, an alkaloid of safflower seed, novel ring system compound, 1,10-diaza-9,20-dioxokabutanes, 2,2′-bisindoles, and (dl)-3a,3a’-bispyrrolo[2,3-b]indoles》. The information in the text is summarized as follows:

Me 1-hydroxyindole-3-acetate produced novel hexacyclic 8,17-bis(methoxycarbonylmethyl)-1,10-diaza-9,20-dioxakabutane as a major product by the reaction with 85% formic acid, while its reaction with trifluoroacetic acid generated exclusively another 2,2′-bisindole dimer, 1-hydroxy-3,3′-di(methoxycarbonylmethyl)-2,2′-bisindole. Reaction of Me 1-hydroxyindole-3-acetate with mineral acid such as HCl afforded Me 5-chloroindole-3-acetate, products and their distribution changed depending on the structure of 1-hydroxyindole. The side chain has a C-C-N structure, enables nucleophilic substitution reaction to occur effectively, and was applied for the preparation of N-feruloylserotonin, an alkaloid isolated from safflower seed. 1-Hydroxymelatonin, having a methoxy group on the benzenoid part, afforded (dl)-3a,3a’-bis(pyrrolo[2,3-b]indole) compound by the treatment with 85% formic acid. Products’ structures are unequivocally determined by X-ray single crystallog. analyses. In the experiment, the researchers used Methyl 2-(5-chloro-1H-indol-3-yl)acetate(cas: 74339-45-0Quality Control of Methyl 2-(5-chloro-1H-indol-3-yl)acetate)

Pradhan, Sourav’s team published research in Organic Letters in 2019 | CAS: 399-52-0

The author of 《Weak Coordination-Guided Regioselective Direct Redox-Neutral C4 Allylation of Indoles with Morita-Baylis-Hillman Adducts》 were Pradhan, Sourav; De, Pinaki Bhusan; Punniyamurthy, Tharmalingam. And the article was published in Organic Letters in 2019. Synthetic Route of C8H6FN The author mentioned the following in the article:

A weak carbonyl coordination-guided regioselective C4 allylation of indoles is demonstrated using the versatile Morita-Baylis-Hillman adduct in the presence of Rh catalysts in a redox-neutral fashion. The substrate scope, functional group diversity, oxidant free character, mechanistic aspects, and synthetic utilities are important practical features. After reading the article, we found that the author used 5-Fluoro-1H-indole(cas: 399-52-0Synthetic Route of C8H6FN)

Anastasiou, Ioannis’s team published research in ChemSusChem 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).Quality Control of 5-Fluoro-1H-indole

《C2-H Arylation of Indoles Catalyzed by Palladium-Containing Metal-Organic-Framework in γ-Valerolactone》 was written by Anastasiou, Ioannis; Van Velthoven, Niels; Tomarelli, Elena; Lombi, Aurora; Lanari, Daniela; Liu, Pei; Bals, Sara; De Vos, Dirk E.; Vaccaro, Luigi. Quality Control of 5-Fluoro-1H-indole And the article was included in ChemSusChem in 2020. The article conveys some information:

An efficient and selective procedure was developed for the direct C2-H arylation of indoles using a Pd-loaded metal-organic framework (MOF) as a heterogeneous catalyst and the nontoxic biomass-derived solvent γ-valerolactone (GVL) as a reaction medium. The developed method allows for excellent yields and C-2 selectivity to be achieved and tolerates various substituents on the indole scaffold. The established conditions ensure the stability of the catalyst as well as recoverability, reusability, and low metal leaching into the solution In the experiment, the researchers used many compounds, for example, 5-Fluoro-1H-indole(cas: 399-52-0Quality Control of 5-Fluoro-1H-indole)