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A procedure has been proposed for the synthesis of 1H-indolylmethylphenols by reaction of hydroxybenzyl alcohols with indoles under conditions implying thermal generation of o- and p-methylenequinones. The mechanism of formation and spectral parameters of the products are discussed.

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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

15-Sep News Discovery of 16066-91-4

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Organothiophosphates have found widespread application as biologically active compounds and synthetic intermediates in medicinal chemistry. The first transition-metal-free one-pot direct synthesis of heterocyclic phosphorothioates involving indole or imidazo[1,2-a]pyridine derivatives, elemental sulfur, and P(O)H compounds is presented. The use of NaI or KI as a catalyst, tert-butyl hydroperoxide as an oxidant, various indole and imidazo[1,2-a]pyridine derivatives are tolerant in this transformation, affording the corresponding products in good to excellent yields. Moreover, this method can be easily adapted to large-scale preparation. O,O-Diethyl S-(1-phenyl-1H-indol-3-yl) phosphorothioate presents potent anti-inflammatory activity in lipopolysaccharide (LPS)-stimulated RAW264.7 cells in a dose-dependent manner. (Figure presented.).

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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

13/9/2021 News Can You Really Do Chemisty Experiments About 16066-91-4

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A highly regioselective and stereoselective cascade annulation of indoles with C2-symmetric enone tethered-cyclohexadienones provides rapid access to complex indole alkaloid-like scaffolds in high yields. Interestingly, a different reaction course was observed with 3-substituted indoles giving C-2/N annulation products with similar complexity via intramolecular aza-Michael addition. This desymmetrization approach is highly practical and allows atom-economical synthesis of natural product-like molecules containing several contiguous stereocenters with broad range of substrate scope and high functional-group tolerance. The synthetic utility of the products was demonstrated with various chemoselective, regioselective, and diastereoselective transformations on the highly strained polycyclic indoles to elaborate the value of this tandem reaction.

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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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By using a strained four-membered ring disilane (3,4-benzo-1,1,2,2-tetraethyldisilacyclobutene) and CsF, a wide range of aryl, alkenyl, alkynyl, benzyl, allyl, and alkyl halides was successfully carboxylated under an ambient CO2 atmosphere (CO2 balloon) at room temperature within 2 h. In this carboxylation, a highly reactive silyl anion, which is generated from the disilane and CsF, is a key to facilitating the formation of a carbanion equivalent. The resulting anionic species can be trapped with CO2 to produce carboxylic acids with high efficiency.

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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

Sep 2021 News Extracurricular laboratory:new discovery of 16066-91-4

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The application of air- and moisture-stable dinuclear palladium(I) complex [Pd(mu-I)(Pt-Bu3)]2 as an efficient catalyst for the Heck cross-coupling reaction of aryl iodides and bromides with acrylates and styrenes is described. The developed protocol is robust and operationally simple and shows a high functional-group tolerance. The employed palladium(I) dimer catalyst is highly robust under these nucleophilic as well as elevated-temperature conditions, allowing its recovery after reaction completion and recycling.

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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

2-Sep-2021 News Awesome Chemistry Experiments For 16066-91-4

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A cross-electrophile coupling reaction of epoxides and (hetero)aryl iodides that operates via the merger of three catalytic cycles involving a Ni-, Ti-, and organic photoredox catalyst has been developed. Three distinct classes of epoxides, styrene oxides, cyclic epoxides, and terminal aliphatic epoxides, all undergo coupling in moderate to good yield and high regioselectivity with the use of three different nitrogen-based ligands for Ni under otherwise identical reaction conditions. The mild reaction conditions accommodate a broad scope of abundant and complex coupling partners. Mechanistic studies suggest that when styrene oxides are employed radical intermediates are involved via Ti-radical ring-opening of the epoxide. Conversely, for terminal aliphatic epoxides, involvement of an iodohydrin intermediate enables the formation of the unexpected linear product.

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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

Brief introduction of 5-Iodo-1H-indole

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The development of a new decarboxylative cross-coupling method that affords terminal and substituted alkynes from various carboxylic acids is described using both nickel- and iron-based catalysts. The use of N-hydroxytetrachlorophthalimide (TCNHPI) esters is crucial to the success of the transformation, and the reaction is amenable to in situ carboxylic acid activation. Additionally, an inexpensive, commercially available alkyne source is employed in this formal homologation process that serves as a surrogate for other well-established alkyne syntheses. The reaction is operationally simple and broad in scope while providing succinct and scalable avenues to previously reported synthetic intermediates.

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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

Archives for Chemistry Experiments of 16066-91-4

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We designed new 3-arylthio- and 3-aroyl-1H-indole derivatives 3?22 bearing a heterocyclic ring at position 5, 6 or 7 of the indole nucleus. The 6- and 7-heterocyclyl-1H-indoles showed potent inhibition of tubulin polymerization, binding of colchicine to tubulin and growth of MCF-7 cancer cells. Compounds 13 and 19 inhibited a panel of cancer cells and the NCI/ADR-RES multidrug resistant cell line at low nanomolar concentrations. Compound 13 at 50 nM induced 77% G2/M in HeLa cells, and at 20 nM caused 50% stable arrest of mitosis. As an inhibitor of HepG2 cells (IC50 = 20 nM), 13 was 4-fold superior to 19. Compound 13 was a potent inhibitor of the human U87MG glioblastoma cells at nanomolar concentrations, being nearly one order of magnitude superior to previously reported arylthioindoles. The present results highlight 13 as a robust scaffold for the design of new anticancer agents.

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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 asymmetric intermolecular, three-component radical-initiated dicarbofunctionalization of 1,1-diarylalkenes with diverse carbon-centered radical precursors and electron-rich heteroaromatics by a copper(I) and chiral phosphoric acid cooperative catalysis strategy has been developed, providing straightforward access to chiral triarylmethanes bearing quaternary all-carbon stereocenters with high efficiency as well as excellent chemo- and enantioselectivity. The key to success is not only the introduction of a sterically demanding chiral phosphoric acid to favor radical difunctionalization over the otherwise remarkable side reactions but also the in situ generation of carbocation intermediates from benzylic radical to realize asymmetric induction with the aid of a removable hydroxy directing group via cooperative interactions with chiral phosphate. Density functional theory calculations elucidated the critical chiral environment created by the hydrogen-bonding and ion-pair interactions between the chiral phosphoric acid catalyst and substrates, which leads to the enantioselective C-C bond formation.

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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

Discovery of 5-Iodo-1H-indole

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A convenient and efficient approach for the synthesis of 2,3-dihydro-2,3?-bisindoles has been developed in good yields via dimerization of N-H indole derivatives. The synthetic utility of this approach was demonstrated by the rapid construction of bisindoles in gram-scale. Biological evaluation revealed that some of the obtained 2,3-dihydro-2,3?-bisindoles exhibited significant in vitro antiproliferative activities on human-derived lung, liver, stomach, and breast cancer cell lines.

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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