Sep 2021 News Awesome and Easy Science Experiments about 3469-20-3

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Catalytic asymmetric N-alkylation of indoles and carbazoles represents a family of important but underdeveloped reactions. Herein, we describe a new organocatalytic strategy in which in situ generated aza-para-quinone methides are employed as the alkylating reagent. With the proper choice of a chiral phosphoric acid and an N-protective group, the intermolecular C?N bond formation with various indole and carbazole nucleophiles proceeded efficiently under mild conditions with excellent enantioselectivity and functional-group compatibility. Control experiments and kinetic studies provided important insight into the reaction mechanism.

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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

10-Sep-2021 News Final Thoughts on Chemistry for 3469-20-3

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Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 3469-20-3, molcular formula is C20H15N, introducing its new discovery. COA of Formula: C20H15N

Photochemical oxidative cyclodehydrogenation reactions are a versatile class of aromatic ring-forming reactions. They are tolerant to functional group substitution and heteroatom inclusion, so can be used to form a diverse range of extended polyaromatic systems by fusing existing ring substituents. However, despite their undoubted synthetic utility, there are no existing models?computational or heuristic?that predict the outcome of photocyclisation reactions across all possible classes of reactants. This can be traced back to the fact that ?negative? results are rarely published in the synthetic literature and the lack of a general conceptual framework for understanding how photoexcitation affects reactivity. In this work, we address both of these issues. We present experimental data for a series of aromatically substituted pyrroles and indoles, and show that quantifying induced atomic forces upon photoexcitation provides a powerful predictive model for determining whether a given reactant will photoplanarise and hence proceed to photocyclised product under appropriate reaction conditions. The propensity of a molecule to photoplanarise is related to localised changes in charge distribution around the putative forming ring upon photoexcitation. This is promoted by asymmetry in molecular structures and/or charge distributions, inclusion of heteroatoms and ethylene bridging and well-separated or isolated photocyclisation sites.

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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

9-Sep-2021 News Top Picks: new discover of C20H15N

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Conjugated azoalkenes 2 react at reflux toluene with fused benzothiadiphosphole 1 (or 4) to give the diazaphosphole 3 in 25-52% yields. With this route it is possible to isolate the so far unknown 3a which is difficult to obtain in other reported conditions. The P atom involved in this cydoaddition is the one between the two S atoms.

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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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Sodium deposited on inorganic supports such as Al2O3, TiO2 and NaCl (‘high-surface sodium’) is a cheap, readily prepared, nonpyrophoric reducing agent for TiCl3. The low-valent titanium thus obtained, after only 1 h reduction time, is well suited for McMurry coupling reactions, particularly of aromatic carbonyl compounds. It exhibits a previously unrivalled template effect for the cyclization of dicarbonyl compounds to (macrocyclic) cycloalkenes and is suitable for the reduction of N-acyl-2-aminobenzophenone derivatives to 2,3-disubstituted indoles. Even a 36-membered ring could be formed without recourse to high dilution techniques.

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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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3-Hydroxy-3H-indoles (1) and their corresponding N-oxides (5) undergo stereospecific reduction at the double C=N bond giving the indoline derivatives (2) and (6) respectively, which, in acidic medium, lose water to give the 2,3-disubstituted indoles (3) and (7) whose physical and spectroscopic data are not in agreement with those reported previously.The structure of 3-hydroxy-2,3-diphenylindoline, one of the reduction products, was determined by X-ray diffraction, and it was shown that hydrogen adds at C-2 cis to the hydroxy-group on C-3. 3,3-Disubstituted-3H-indoles with two organic radicals on C-3 give a mixture of stereoisomers.

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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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The reaction of indoles with copper(II) chloride has been studied in acetonitrile.At low copper(II):indole ratios, dimers are formed in the presence of dioxygen, oxygenated products are obtained, and at large copper(II):indole ratios, pyrrole ring-chlorinated products are formed in yields of up to 92percent.The reactions are postulated to proceed via the radical cations of the indoles formed in an electron-transfer 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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A convenient and efficient method for the construction of indole skeleton was developed via Pd-catalyzed C-H activation of N-aryl amides and subsequent coupling with alkynes. Both stoichiometric and catalytic versions have been successfully achieved.

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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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N-Formylindoles (1A-H) exhibit pronounced aldehydic character as revealed by the formation of 4-nitrophenylhydrazones (2A-E) and 2,4-dinitrophenylhydrazones (2F-J).The N-formylindoles (1E-G) bearing phenyl groups at 2- and 3-positions do not form either 4-nitrophenylhydrazones or 2,4-dinitrophenylhydrazones probably owing to steric hindrance.The N-formylindoles (1C-F) which bear a substituent at 2-position but none at 7-position exist only in one conformation, while those bearing either substituents at both 2- and 7-positions (i. e. 1G) or no substituent at all (i. e. 1A, 1B) exist in two conformations as shown by their PMR spectra.While the 4-nitrophenylhydrazones (2A-E) show expected fragmentation pattern, the 2,4-dinitrophenylhydrazones exhibit some interesting fragmentation pathways involving the successive loss of two OH radicals and N2 under electron impact.

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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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Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 3469-20-3, molcular formula is C20H15N, introducing its new discovery. name: 2,3-Diphenyl-1H-indole

A method for catalytic synthesis of indole compounds (by machine translation)

The invention discloses a process for catalytic synthesis of indole compounds, comprising the following steps : (1) the adjoining nitrostyrolene or its derivatives, frequency that alcohol esterjoint boric acid, alkali and lower saturated monohydric alcohol reaction stirring under a nitrogen atmosphere ; (2) the step (1) cooling to room temperature, the reaction product of, adding ethyl acetate to be fully mixed, filtered, washed with ethyl acetate ; (3) steps turns on lathe does (2) the organic phase of the material of the lower saturated monohydric alcohol, a silica gel column, then by the petroleum ether and ethyl acetate for the elution agent leaching the above-mentioned silica gel column, the product to be purified, i.e. the indole compound. Process for catalytic synthesis of this invention under the neutral condition, by utilizing cheap joint boric acidfrequency that ester as the raw material, by friendly lower saturated monohydric alcohol used as a solvent, by a simple operation to obtain the indole compound, cheap raw material cost, high efficiency, good safety, has a wide range of expansibility, and good industrial application prospects. (by machine translation)

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Reference£º
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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Synthesis of indoles from aroyloxycarbamates with alkynes: Via decarboxylation/cyclization

An efficient Pd-catalyzed decarboxylation/cyclization of aroyloxycarbamates to realize substituted indoles has been disclosed. Terminal alkynes as the coupling partners lead to site specific 2-substituted indoles through two pathways, while internal alkynes with aroyloxycarbamates can be transformed to 2,3-disubstituted indoles directly. This protocol is further demonstrated by the efficient synthesis of indoles as well as the success of employing inexpensive aryl acids as starting materials to construct C-N bonds by releasing CO2.

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Reference£º
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