27816-52-0

Usage

Type of compound

Heterocyclic aromatic organic compound

Derivative of

Indole

Physical state at room temperature

Colorless to light yellow liquid

Usage

Building block in the synthesis of pharmaceutical compounds and agrochemicals

Odor

Strong, unpleasant

Hazardous nature

Inhalation, ingestion, or skin absorption can be harmful

Potential applications

Medical and agricultural industries

Structural properties

Diverse chemical reactivity

Upstream product

• 16096-32-5 4-methyl-1H-indole 
• 74-88-4 methyl iodide 
• 23492-98-0 1,4-dimethyl-3-nitropyridinium iodide 
• 67-64-1 acetone 
• 74-89-5 methylamine 
• 696-44-6 N-methyl-m-toluidine 
• 6639-59-4 N-(2,3-dimethylphenyl)formamide 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 1444-12-8 1-methyl-1H-indole-4-carboxylic acid methyl ester 
• 1379516-31-0 C₁₅H₂₀N₂O₂ 
• 1352334-73-6 diethyl-carbamic acid 1-methyl-1H-indol-5-yl ester 
• 6407-34-7 methyl-1 ethylideneamine 

Downstream Products

• 170489-16-4 1,4-dimethyl-1H-indole-3-carbaldehyde 
• 23967-51-3 1,4-Dimethyl-1H-indol-2-carboxylic acid 
• 132554-34-8 1,4-dimethyl-2-phenyl-1H-indole 
• 1315257-97-6 N-(3-chloro-1,4-dimethyl-1H-indol-2-yl)-N,4-dimethylbenzenesulfonamide 
• 1315257-83-0 N-(1,4-dimethyl-1H-indol-2-yl)-N,4-dimethylbenzenesulfonamide 
• 1356053-15-0 C₂₅H₂₂N₂O 
• 1360059-29-5 1,4-dimethyl-N-p-tolyl-N-tosyl-1H-indol-2-amine 

Relevant academic research and scientific papers

SYNTHESIS OF INDOLES FROM PYRIDINIUM SALTS

The detailed analysis of the products of the interaction of nitropyridinium salts with ketones and alkylamines resulted in new data testifying in favor of the previously proposed scheme for the formation of indoles from pyridinium salts.

SYNTHESIS OF INDOLES FROM PYRIDINIUM SALTS. 1. RECYCLIZATION OF 4-ALKYL-2,6-DIMETHYL-3-NITROPYRIDINE METHIODIDES IN THE PRESENCE OF KETONES

A method for the synthesis of 4-alkylpolymethylindoles by recyclization of 4-alkyl-2,6-dimethyl-3-nitropyridine methiodides in the presence of ketones was developed.A method for establishing the structures of the polyalkylindoles on the basis of data from the PMR spectra and the proton-coupled 13C NMR spectra is proposed.

Cobalt-Catalyzed Enantioselective C–H Arylation of Indoles

Atropoisomeric (hetero)biaryls are scaffolds with increasing importance in the pharmaceutical and agrochemical industries. Although it is the most obvious disconnection to construct such compounds, the direct enantioselective C–H arylation through the concomitant induction of the chiral information remains extremely challenging and uncommon. Herein, the unprecedented earth-abundant 3d-metal-catalyzed atroposelective direct arylation is reported, furnishing rare atropoisomeric C2-arylated indoles. Kinetic studies and DFT computation revealed an uncommon mechanism for this asymmetric transformation, with the oxidative addition being the rate- and enantio-determining step. Excellent stereoselectivities were reached (up to 96% ee), while using an unusual N-heterocyclic carbene ligand bearing an essential remote substituent. Attractive dispersion interactions along with positive C–H-π interactions exerted by the ligand were identified as key factors to guarantee the excellent enantioselection.

Copper-Catalyzed Synthesis of Indolyl Benzo[b]carbazoles and Their Photoluminescence Property

A copper-catalyzed cascade cyclization of dihydroisobenzofurans with indoles for the rapid construction of indoly benzo[b]carbazoles has been reported, providing the desired products in moderate to good yields under mild conditions along with a broad substrate scope and good functional group tolerance. The photoluminescence property of these indoly benzo[b]carbazoles has also been investigated.

Assembly of polycyclic N-heterocycles: Via copper-catalyzed cycloamination of indolylquinones and aromatic amines

The copper-catalyzed cycloamination of indolylquinones and various (hetero)aromatic amines under ligand-free conditions for the synthesis of polycyclic N-heterocycles has been developed. This method allows facile access to polycyclic N-heterocycles with the tolerance of chloride, bromide, amino, thio, etc. groups in moderate to high yields (60-89%).

Visible-Light-Induced Carbonylation of Indoles with Phenols under Metal-Free Conditions: Synthesis of Indole-3-carboxylates

A visible-light-induced carbonylation of indoles with phenols for the synthesis of indole-3-carboxylates has been developed. The reaction proceeded via a radical carbonylation process in which elementary I2 was used as an effective photosensitive initiator and, thus, avoided the use of transition metal catalysts. A series of different aryl indole-3-carboxylates were prepared in moderate to good yields. The broad applicability of this methodology was further highlighted by the late-stage functionalization of several phenol-containing natural products and pharmaceuticals.

Salicylaldehyde-Promoted Cobalt-Catalyzed C-H/N-H Annulation of Indolyl Amides with Alkynes: Direct Synthesis of a 5-HT3 Receptor Antagonist Analogue

A cobalt-catalyzed annulation of the C(sp2)-H/N-H bond of indoloamides with alkynes assisted by 8-aminoquinoline is reported for the synthesis of six-membered indololactams. The use of salicylaldehyde as the ligand is crucial for this transformation. The protocol has a broad scope for both alkynes and indoles. Preparing an active Co complex illustrates that salicylaldehyde plays a key role in the C-H activation step. The synthetic applications are proven by the gram-scale reaction and one-step construction of the multicyclic 5-HT3 receptor antagonist.

Straightforward access to novel indolo[2,3-: B] indoles via aerobic copper-catalyzed [3+2] annulation of diarylamines and indoles

Herein, we report an unprecedented aerobic copper-catalyzed [3+2] annulation reaction of diarylamines with indoles, which allows direct access to novel 2-diarylaminoindolo[2,3-b]indoles, a class of potential photoelectric device molecules. The developed transformation proceeds with broad substrate scope, good functional group tolerance, high chemo-selectivity, and no need for pre-preparation of specific agents, which offers a practical route for diverse and atom-economic synthesis of the desired products that are difficult to prepare with the conventional approaches.

Synthesis of Cyclopenta[b]indoles via a Formal [3+2] Cyclization of N-Sulfonyl-1,2,3-triazoles and Indoles

Annulation of benzoxy-tethered N-sulfonyl-1,2,3-triazoles and indoles has been developed in this paper, providing an efficient and convenient access to valuable cyclopenta[b]indoles in moderate to good yields. α,β-Unsaturated imine, which generated in situ from denitrogenation and 1,2-OBz migration of triazole, provided three carbons for the formal [3+2] cyclization reaction for the first time. (Figure presented.).

Catalytic Aerobic Dehydrogenatin of N-Heterocycles by N-Hydoxyphthalimide

Catalytic methods for the aerobic dehydrogenation of N-heterocycles are reported. In most cases, indoles are accessed efficiently from indolines using catalytic N-hydroxyphthalimide (NHPI) as the sole additive under air. Further studies revealed an improved catalytic system of NHPI and copper for the preparation of other heteroaromatics, for example quinolines. (Figure presented.).