53475-25-5

Upstream product

• 54431-10-6 butyrophenone phenylhydrazone 
• 71149-35-4 3-ethyl-2-phenyl-3H-indol-3-ol 
• 622-76-4 1-phenyl-1-butyne 
• 615-43-0 2-iodophenylamine 
• 114-83-0 1-acetyl-2-phenylhydrazine 
• 62-53-3 aniline 
• 59-88-1 phenylhydrazine hydrochloride 
• 495-40-9 propiophenone 
• 42116-43-8 tert-butyl 2-phenylhydrazine-1-carboxylate 
• 615-36-1 2-bromoaniline 
• 948-65-2 2-phenyl-indole 
• 64-17-5 ethanol 
• 577-19-5 2-nitrophenyl bromide 
• 95-51-2 o-chloroaniline 

Downstream Products

• 791786-07-7 3-ethyl-1,2-diphenyl-1H-indole 
• 83824-22-0 N-(2,4-Dinitro-phenyl)-N'-[1-(3-ethyl-2-phenyl-indol-1-yl)-meth-(E)-ylidene]-hydrazine 
• 83824-17-3 N-[1-(3-Ethyl-2-phenyl-indol-1-yl)-meth-(E)-ylidene]-N'-(4-nitro-phenyl)-hydrazine 
• 83824-11-7 3-ethyl-2-phenylindole-1-carboxaldehyde 
• 99290-14-9 1-(3-ethyl-2-phenyl-1H-indol-1-yl)ethan-1-one 

Relevant academic research and scientific papers

Synthesis of Ester-Substituted Indolo[2,1-a]isoquinolines via Photocatalyzed Alkoxycarbonylation/Cyclization Reactions

A direct alkoxycarbonylation/cyclization reaction is accomplished under visible light-induced photoredox catalysis. With this approach, a variety of ester-substituted indolo[2,1-a]isoquinolines are prepared in good to excellent yields. It is worth noting that this method not only can afford the synthesis of indolo[2,1-a]isoquinolines but also can provide an alternative route for generating complex target structures bearing carboxylic esters.

Modular counter-Fischer?indole synthesis through radical-enolate coupling

A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.

One-pot oxidative hydrolysis-oxidative cleavage of 7-borylindoles enables access to: O -amidophenols and 4-acylbenzoxazoles

7-Borylindoles undergo a one-pot oxidative-hydrolysis of the arylboronate and oxidative cleavage of the indole C2-C3 double bond to afford o-amidophenol derivatives. Subsequent cyclisation delivers benzoxazoles bearing an acyl group at C4, a substitution pattern common to fungal-derived benzoxazole alkaloids. Using 7-borylindoles as substrates to access functionalised o-amidophenols circumvents the difficult preparation of these compounds from arenes, streamlining access to substituted 4-acylbenzoxazoles in the process.

Pd-Catalyzed Reductive Cyclization of Nitroarenes with CO2 as the CO Source

A reductive amination process that constructs indoles, carbazoles or benzimidazoles from nitroarenes – irrespective of their electronic or steric nature – was developed that uses CO2 as the source of CO. The process is robust, tolerating common gaseous components of flue gas (H2S, SO2, NO and H2O) without adversely affecting the reductive cyclization.

Method for preparing indole compounds by using rhodium/carbon as catalyst

The invention provides a method for preparing indole compounds by using rhodium/carbon as a catalyst. Corresponding indole compounds are formed through subjecting aniline and analogs thereof and alkyne to a catalytic cyclization reaction in the presence of the rhodium/carbon. The method has the beneficial effects that the preparation method is simple in process, the raw materials are cheap and readily available, the yield is high, inert-gas protection is not required, and the reaction temperature is relatively moderate.

A palladium/carbon as catalyst preparation of indole compounds method (by machine translation)

The present invention provides a palladium/carbon as catalyst preparation of indole compounds method, aniline and its analogs in the palladium/carbon with the alkyne under the action of the catalytic cyclization reaction, to form the corresponding indoles. This method has the advantages of: simple preparation method, the raw material is cheap, high yield, without protection of inert gas, the reaction temperature is relatively mild. (by machine translation)

N, N-Dimethylformamide-stabilized palladium nanoclusters as a catalyst for Larock indole synthesis

We show that N,N-dimethylformamide-stabilized Pd nanoclusters (NCs) have high catalytic activity in the reaction of substituted 2-iodoanilines with alkynes to give 2,3-disubstituted indoles. This indole synthesis does not require phosphine ligands and proceeds with low Pd catalyst loadings. The Pd NCs were separated from the mixture after the reaction, and recycled at least three times. Transmission electron microscopy images showed that the Pd particle size before the reaction was 1.5-2.5 nm. The particle size after the reaction was 2-3 nm. X-ray photoelectron spectroscopy showed that the binding energy of the Pd NCs before the reaction was 335.0 eV.

Iron-Catalyzed Reductive Cyclization of o-Nitrostyrenes Using Phenylsilane as the Terminal Reductant

Using microscale high-throughput experimentation, an efficient, earth-abundant iron phenanthroline complex was discovered to catalyze the reductive cyclization of ortho-nitrostyrenes into indoles via nitrosoarene reactive intermediates. This method requires only 1 mol % of Fe(OAc)2 and 1 mol % of 4,7-(MeO)2phen and uses phenylsilane as a convenient terminal reductant. The scope and limitations of the method were illustrated with 21 examples, and an investigation into the kinetics of the reaction revealed first-order behavior in catalyst and silane and zero-order behavior with respect to nitrostyrene.

Cobalt(III)-Catalyzed Redox-Neutral Synthesis of Unprotected Indoles Featuring an N-N Bond Cleavage

A redox-neutral cobalt(III)-catalyzed synthetic approach for the direct synthesis of unprotected indoles showcasing an N-N bond cleavage is reported. The herein newly introduced Boc-protected hydrazines establish a beneficial addition to the limited portfolio of oxidizing directing groups for cobalt(III) catalysis. Moreover, the developed catalytic methodology tolerates a good variety of functional groups.

Novel and Efficient Heterogeneous 4-Methylbenzenesulfonic Acid-Based Ionic Liquid Supported on Silica Gel for Greener Fischer Indole Synthesis

In this work, a functionalizing active species 4-methylbenzenesulfonic acid-based IL on silica gel (IL-SO3H-SiO2) has been prepared, and characterized by FT-IR, XRD, TGA, SEM and EDX spectra. Then, IL-SO3H-SiO2 was utilized as an efficient and heterogeneous catalyst for the synthesis of indoles via the one-pot Fischer reaction of phenyl hydrazines with ketones or aldehydes at room temperature. The heterogeneous catalyst could be recovered easily by filtration and reused many times without significant loss of its catalytic activity.