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Highly efficient and facile green approach for one-pot fischer indole synthesis

A simple, efficient and an environmental friendly method have been developed for the synthesis of substituted indole from aryl hydrazines and aldehydes/ ketones with HPA-phosphomolybdic acid as a heterogeneous catalyst. The catalyst is nontoxic and recyclable.

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3-(4-Fluoropiperidin-3-yl)-2-phenylindoles as high affinity, selective, and orally bioavailable h5-HT2A receptor antagonists

The development of very high affinity, selective, and bioavailable h5-HT2A receptor antagonists is described. By investigation of the optimal position for the basic nitrogen in a series of 2-phenyl-3-piperidylindoles, it was found that with the basic nitrogen at the 3-position of the piperidine it was not necessary to further substitute the piperidine in order to obtain good binding at h5-HT2A receptors. This meant the compounds no longer had high affinity at the IKr potassium channel, an issue with previous series of 2-aryl-3-(4-piperidyl)indoles. Improvements could be made to oral bioavailability in this series by reduction of the pKa of the basic nitrogen, by adding a fluorine atom to the piperidine ring, leading to 3-(4-fluoropiperidin-3-yl)-2-phenyl-1H-indole (17). Metabolic studies with this compound identified oxidation at the 6-position of the indole as a major route in vitro and in vivo in rats. Blocking this position with a fluorine atom led to 6-fluoro-3-(4-fluoropiperidin-3-yl)-2-phenyl-1H-indole (22), an antagonist with 0.06 nM affinity for h5-HT2A receptors, with bioavailability of 80% and half-life of 12 h in rats.

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Indium-HI-mediated one-pot reaction of 1-(2-arylethynyl)-2-nitroarenes to 2-arylindoles

While 1-(2-arylethynyl)-2-nitroarenes were reduced to 2-(2-arylethynyl)anilines in the presence of indium and InCl3 in THF/H2O (v/v = 5/1) at 50 C, 1-(2-arylethynyl)-2-nitroarenes were reductively cyclized to 2-arylindoles with good yields in the presence of indium and aqueous HI in benzene.

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Impregnated copper or palladium-copper on magnetite as catalysts for the domino and stepwise Sonogashira-cyclization processes: A straightforward synthesis of benzo[b]furans and indoles

An impregnated copper on magnetite catalyst is a versatile system for different domino Sonogashira-cyclization processes between 2-iodophenol and different alkynes to give the corresponding substituted benzo[b]furans. The catalyst could be recovered ten times without losing its activity. The related process using 2-iodoaniline was, however, better catalyzed by mixed palladium-copper on magnetite giving exclusively, in this case, the products arising from the Sonogashira coupling. The cyclization to the corresponding substituted indoles could be easily and quantitatively performed by zinc bromide treatment. This catalyst avoids the use of any type of expensive and difficult to handle organic ligand, showing excellent yields, under mild reaction conditions. The catalyst is very easy to remove from the reaction medium, just by using a simple magnet.

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A New Route to Indolo<3,2-b>isoquinolines

2-Phenylindole-3-carbaldoximes (2a-d) on cyclization with alcoholic sulphuric acid give delta-carbolines, indolo<3,2-b>-isoquinolines (5a-d) and not the gamma-carbolines.This constitutes a new route to delta-carbolines.

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A trifluoromethyl substituted 3, 3′ – double (2 – phenyl-indolyl) methane compound synthesis method (by machine translation)

The invention belongs to the technical field of chemical synthesis of the fluorine, relates to a synthetic trifluoromethyl substituted 3, 3 ‘- double (2 – phenyl-indolyl) methane compound of method, in order to 2 – phenyl indole as substrate, trifluoromethyl bromide as the alkyl radical source, in under the action of the Cu catalyst, di-tert-butyl peroxide DTBP or too […] diisopropyl benzene as the oxidizing agent, the tertiary butyl alcohol potassium, potassium […] or methanol as alkali, trifluoro methane sulfonic acid or trifluoro methane sulfonic acid magnesium silver as the Lewis acid, 1, 2 – dichloroethane as the solvent under the conditions of the DCE, one-step synthesis of trifluoromethyl substituted 3, 3’ – double (2 – phenyl-indolyl) methane compound. The synthesis method has the operation is simple, cheap and easy to obtain, the diversification of the product and the like. (by machine translation)

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PROCESSES FOR PREPARING INDOLES

Methods for the synthesis of an indole in provided. Methods comprise oxidizing a N-aryl imine in the presence of a palladium-based catalyst, an oxidant, and a solvent.

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SBA-15-Pr-SO3H catalyzed one-pot synthesis of indole derivatives via Fischer indole pathway

In this work, an efficient, user-friendly, and simple procedure was reported for the preparation of indole derivatives catalyzed by the heterogeneous SBA-15-Pr-SO3H via Fischer indole pathway. The title compounds were synthesized from various arylhydrazines and ketones in the presence of 3 mol% of the catalyst in the refluxing ethanol.

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Synthesis of 2-Substituted Indoles through Visible Light-Induced Photocatalytic Cyclizations of Styryl Azides

A visible light-induced photocatalytic intramolecular cyclization of styryl azides has been developed in the presence of the ruthenium complex Ru(bpy)3Cl2 (0.5 mol%) as photocatalyst at room temperature. The present photocatalytic strategy features operational simplicity as well as high functional group tolerance, and provides a facile access to various 2-substituted N-free indoles in good to excellent yields. Importantly, the present process can employ sunlight as the light source to afford the corresponding products without loss of reaction efficiency.

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IrIII-Catalyzed One-Pot Cascade Synthesis of Pentacyclic-Fused Carbazoles from Indoles and Diazoes

A highly efficient IrIII-catalyzed cascade cyclization of indoles and diazoes giving access to unique pentacyclic-fused carbazoles has been developed. This novel strategy expanded the application scope of coupling partners to take diazo compounds as a C2 source, and two new cycles, three new C?C and one new C?N bonds were formed in one-pot.

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