41018-81-9

Usage

Core structure

Benzene ring fused to a five-membered pyrrole ring

Substitution

Methyl groups at positions 3 and 5, phenyl group at position 2

Physical state at room temperature

White to off-white solid

Odor

Distinct

Uses

Building block in organic synthesis, found in natural products and pharmaceuticals, production of dyes and perfumes.

Upstream product

• 106-49-0 p-toluidine 
• 7647-01-0 hydrogenchloride 
• 106989-73-5 1-phenyl-1-(phenylamino)propan-2-one 
• 637-60-5 p-tolylhydrazine hydrochloride 
• 93-55-0 1-phenyl-propan-1-one 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 539-44-6 N-4-methylphenylhydrazine 
• 673-32-5 1-Phenylprop-1-yne 
• 583-68-6 2-bromo-p-toluidine 
• 1855-09-0 1-phenyl-1,2-propandiol 
• 4436-22-0 1-phenylpropylene oxide 
• 59-88-1 phenylhydrazine hydrochloride 

Downstream Products

• 41019-33-4 3,5-dimethyl-2-phenyl-3H-indol-3-yl hydroperoxide 
• 41019-19-6 N-(2-acetyl-4-methylphenyl)benzamide 

Relevant academic research and scientific papers

Metal-Free Visible-Light Promoted Radical Cyclization to Access Perfluoroalkyl-Substituted Benzimidazo[2,1-a]isoquinolin-6(5H)-ones and Indolo[2,1-a]isoquinolin-6(5H)-ones

A metal-free visible-light-induced cyclization procedure was developed for the rapid synthesis of perfluoroalkyl-substituted benzimidazo[2,1-a]isoquinolin-6(5H)-ones and perfluoroalkyl-substituted indolo[2,1-a]isoquinolin-6(5H)-ones under mild reaction conditions. In this procedure, the formation of electron-donor-acceptor (EDA) complex is critical for the visible-light promoted process to avoid the utilization of external photocatalysts. (Figure presented.).

Rhodium(III)-catalyzed c-h activation and indole synthesis with hydrazone as an auto-formed and auto-cleavable directing group

An efficient, practical, and external-oxidant-free indole synthesis from readily available aryl hydrazines was developed, by using hydrazone as a directing group for RhIII-catalyzed C-H activation and alkyne annulation. The hydrazone group was formed by in situ condensation of hydrazines and Ci￡O source, whereas its N-N bond was served as an internal oxidant, for which we termed it as an auto-formed and auto-cleavable directing group (DGauto). This method needs no step for pre-installation and post-cleavage of the directing group, making it a quite easily scalable approach to access unprotected indoles with high step economy. The DGauto strategy was also applicable for isoquinoline synthesis. In addition, synthetic utilities of this chemistry for rapid assembly of π-extended nitrogen-doped polyheterocycles and bioactive molecules were demonstrated. Copyright

Ruthenium-catalyzed synthesis of indoles from anilines and epoxides

A general synthetic route to indoles from readily available anilines and epoxides by using ruthenium catalysis is described. This straightforward transformation allows a variety of indoles to be obtained in good yields by using [Ru3(CO)12]/1,1-bis(diphenylphosphino)ferrocene as the catalytic system. Water and hydrogen are formed as the only stoichiometric by-products, making this process highly atom efficient.

The regioselective Larock indole synthesis catalyzed by NHC-palladium complexes

The first practical and regioselective process for the synthesis of 2,3-disubstituted indoles from the reaction of o-iodoanilines or o-bromoanilines and their derivatives with symmetrical and unsymmetrical internal alkynes catalyzed by a ferrocene-functionalized N-heterocyclic carbene (NHC)-palladium complex has been developed, and the indoles were isolated in good yields with high regioselectivity.

Improved indole syntheses from anilines and vicinal diols by cooperative catalysis of ruthenium complex and acid

By developing a new and efficient dinuclear catalyst [Ru(CO) 2(Xantphos)]2 [Xantphos = 4,5-bis(diphenylphosphino)-9,9- dimethyl-9H-xanthene], an improved synthesis of indole from vicinal diols and anilines by cooperative catalysis of ruthenium complex and p-TSA (para-toluenesufonic acid) has been demonstrated. The presented synthetic protocol allows assembling a wide range of products in an efficient manner. Comparing to the existed protocols, our indole syntheses can be achieved at lower reaction temperature, in shorter reaction time, and with improved substrate tolerance.

One-pot-one-step, microwave-assisted Fischer indole synthesis

The Fischer indole synthesis was carried out using microwaves instead of conventional heating procedures. When the mixture of phenylhydrazine, cyclohexanone and zinc chloride was irradiated at 600 W for 3 min, 76% of 1,2,3,4-tetrahydrocarbazole was obtained. However, when zinc chloride was replaced with p-toluenesulfonic acid (p-TSA), the reaction yielded 91% of 1,2,3,4-tetrahydrocarbazole. Thus, a series of indoles were prepared using microwaves in the presence of p-TSA catalyst.

Regioselective Pd-catalyzed indolization of 2-bromoanilines with internal alkynes using phosphine-free ligands

The possibility of using phosphine-free ligands to promote Pd-catalyzed indolization of 2-bromoanilines with internal alkynes was examined for the first time. Phenylurea was found to be the optimal ligand, which could mediate the synthesis of 2,3-disubsti

Comparative studies on conventional and microwave synthesis of some benzimidazole, benzothiazole and indole derivatives and testing on inhibition of hyaluronidase

We have synthesized twelve 2-substituted benzimidazole, benzothiazole and indole derivatives using on both microwave irradiation and conventional heating methods. The microwave method was observed to be more beneficial as it provides an increase of yield from 3% to 113% and a 95 to 98 % reduction in time. All compounds were tested by a stains-all assay at pH 7 and by a Morgan-Elson assay at pH 3.5 for hyaluronidase inhibitory activity at a concentration of 100 μM. The most potent compound was 2-(4-hydroxyphenyl)-3-phenylindole (12) with an IC50 value of 107 μM at both pH 7 and 3.5.

Zn(OTf)2-catalyzed cyclization of proparyl alcohols with anilines, phenols, and amides for synthesis of indoles, benzofurans, and oxazoles through different annulation mechanisms

Zn(OTf)2 (10 mol %) catalyzed the cyclization of propargyl alcohols with PhXH (X = O, NH) in hot toluene (100 °C) without additive and gave indole and benzofuran products with different structures. In such transformations, α-carbonyl intermedia

Fischer indole synthesis in the absence of a solvent

The traditional Fischer synthesis of indoles has been investigated and it has been shown that the reaction proceeds in good yield in the absence of a solvent.