576-15-8

Usage

Uses

1. Used in Organic Synthesis:
1-Acetylindole is used as a synthetic intermediate for the stereocontrolled synthesis of (±)-geissoschizine, a naturally occurring alkaloid with potential biological activities. Its unique structure and reactivity make it a valuable building block in the development of novel compounds with various applications.
2. Used in Coordination Chemistry:
In the field of coordination chemistry, 1-Acetylindole is used in the preparation of (1-acetyl-κO-indolyl-κC2)tetracarbonylmanganese through a standard cyclomanganation procedure. This application highlights its utility in the formation of metal complexes, which can have potential uses in catalysis, materials science, and other areas of chemistry.

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 2151, 1988 DOI: 10.1016/S0040-4039(00)86696-4

InChI:InChI=1/C10H9NO/c1-8(12)11-7-6-9-4-2-3-5-10(9)11/h2-7H,1H3

Upstream product

• 99293-86-4 N-acetylindolin-3-ol 
• 50794-23-5 o-formylphenylglycine 
• 108-24-7 acetic anhydride 
• 112030-93-0 (Z)-2-(2-ethoxyethenyl)acetanilide 
• 74422-09-6 cis-3-acetyl-2a,7b-dihydro-3H-cyclobutindole 
• 112030-93-0 N-[2-((E)-2-Ethoxy-vinyl)-phenyl]-acetamide 
• 120-72-9 indole 
• 75-36-5 acetyl chloride 
• 26340-49-8 2-iodo-1H-indole 
• 105-36-2 ethyl bromoacetate 
• 61403-29-0 N-(2-ethynylphenyl)acetamide 
• 614-76-6 N-acetyl-2-bromoaniline 
• 1496-76-0 N-benzoylindole 
• 74422-10-9 1-benzoyl-1H-1-benzazepine 

Downstream Products

• 703-80-0 3-acetylindole 
• 81223-73-6 1-(1H-indol-6-yl)ethan-1-one 
• 99113-93-6 1-acetyl-2-(2,5-dimethylphenyl)indole 
• 17537-64-3 1,3-diacetyl-1H-indole 
• 155703-10-9 1,6-diacetylindole 
• 92013-04-2 1-Acetyl-6-chloroacetylindole 
• 21905-78-2 N-acetyloxindole 
• 16800-68-3 1-acetyl-2,3-dihydro-1H-indol-3-one 
• 99893-12-6 1-acetyl-2-(m-chlorobenzoyloxy)-3-hydroxyindoline 
• 78388-91-7 1-(2-phenylindol-1-yl)ethanone 
• 120-72-9 indole 
• 71-50-1 acetate 
• 64-19-7 acetic acid 
• 10604-59-8 N-Ethylindole 

Relevant academic research and scientific papers

Synthesis and characterization of Trichloroisocyanouric acid functionalized mesoporous silica nanocomposite (SBA/TCCA) for the Acylation of Indole

Trichloroisocyanouric acid (TCCA)-functionalized mesoporous silica nanocomposites (SBA/ TCCA) were synthesized and characterized for the acylation of indole. The uniform incorporation of TCCA inside the SBA-15 matrix was confirmed by standard characteriza

HETEROCYCLIC SYNTHESIS VIA THALLATION AND SUBSEQUENT PALLADIUM-PROMOTED OLEFINATION

The thallation and subsequent palladium-promoted olefination of p-tolylacetic acid, N-methylbenzamide, benzamide and acetanilide provides a novel new route to a variety of important oxygen and nitrogen heterocycles.

An efficient catalytic method for the c-n acylation of heterocycles by schiff base co(Ii), ni(ii), cu(ii) and zn(ii) transition metal complexes

The catalytic activity of Schiff base Co(II), Ni(II), Cu(II) and Zn(II) transition metal complexes was tested for N-Acylation of heterocycles with acetyl chloride. It is observed that all the complexes worked as efficient catalysts. The structural type of complexes was studied by an X-ray powder diffractogram (XRD). The mixed ligand complexes with PPh3 ligand show greater activity as compared to Phen complexes and Schiff base complexes. Especially complex [Ni(L)(PPh3)2Cl2] efficiently worked as a catalyst because of high thermal stability (TGA-DSC) and large catalytic surface area (BET).

A Catalytic Construction of Indoles via Formation of Ruthenium Vinylidene Species from N-Arylynamides

Treatment of ynamides with a catalytic amount of TpRuCl(PPh3)2 resulted in the construction of indole scaffolds known as privileged structure motifs. This reaction involved a cascade of 1,2-rearrangement and cyclization carrying out C?C bond formation via a ruthenium vinylidene intermediate, as revealed by a deuterium-labeling experiments. Furthermore, the transformation of multi-functionalized ynamide, derived from a practical drug molecule, showed a high functional group tolerance of this reaction. (Figure presented.).

Iodine-catalyzed convergent aerobic dehydro-aromatization toward benzazoles and benzazines

An iodine-catalyzed aerobic dehydro-aromatization has been developed, providing straightforward and efficient access to various benzoazoles and benzoazines. The present transition-metal-free protocol enables the dehydro-aromatization of tetrahydrobenzazoles and tetrahydroquinolines with molecular oxygen as the green oxidant, along with some other N-heterocycles. Hence, a broad range of heteroaromatic compounds are generated in moderate to good yields under facile reaction conditions.

Aerobic oxidative dehydrogenation of N-heterocycles over OMS-2-based nanocomposite catalysts: Preparation, characterization and kinetic study

OMS-2-based nanocomposites doped with tungsten were prepared for the first time and their remarkably enhanced catalytic activity and recyclability in aerobic oxidative dehydrogenation of N-heterocycles were examined in detail. Many tetrahydroquinoline derivatives and a broad range of other N-heterocycles could be tolerated by the catalytic system using a biomass-derived solvent as a reaction medium. Newly generated mixed crystal phases, noticeably enhanced surface areas and labile lattice oxygen of the OMS-2-based nanocomposite catalysts might contribute to their excellent catalytic performance. Moreover, a kinetic study was extensively performed which concluded that the dehydrogenation of 1,2,3,4-tetrahydroquinoline is a first-order reaction, and the apparent activation energy is 29.66 kJ mol-1

Ir-Catalyzed Reversible Acceptorless Dehydrogenation/Hydrogenation of N-Substituted and Unsubstituted Heterocycles Enabled by a Polymer-Cross-Linking Bisphosphine

The polystyrene-cross-linking bisphosphine ligand PS-DPPBz was effective for the Ir-catalyzed reversible acceptorless dehydrogenation/hydrogenation of N-heterocycles. Notably, this protocol is applicable to the dehydrogenation of N-substituted indoline derivatives with various N-substituents with different electronic and steric natures. A reaction pathway involving oxidative addition of an N-adjacent C(sp3)-H bond to a bisphosphine-coordinated Ir(I) center is proposed for the dehydrogenation of N-substituted substrates.

Ascorbic Acid as an Aryl Radical Inducer in the Gold-Mediated Arylation of Indoles with Aryldiazonium Chlorides

In recent years interest in the development of protocols that facilitate the oxidative addition of gold to access mild cross-coupling processes mediated by this metal has increased. In this context, we report herein that ascorbic acid, a natural and readily accessible antioxidant, can be used to accelerate the oxidative addition of aryldiazonium chlorides onto AuI. The aryl–AuIII species generated in this way, has been used to prepare 3-arylindoles in a one-pot protocol starting from anilines and para-, meta-, and ortho- substituted aryldiazonium chlorides. The mechanism underlying the oxidative addition has been examined in detail based on EPR analyses, cyclic voltammetry, and DFT calculations. Interestingly, we have found that in this protocol, the chloride atom induces the AuII/AuIII oxidation step.

Efficient acceptorless photo-dehydrogenation of alcohols and: N -heterocycles with binuclear platinum(ii) diphosphite complexes

Although photoredox catalysis employing Ru(ii) and Ir(iii) complexes as photocatalysts has emerged as a versatile tool for oxidative C-H functionalization under mild conditions, the need for additional reagents acting as electron donor/scavenger for completing the catalytic cycle undermines the practicability of this approach. Herein we demonstrate that photo-induced oxidative C-H functionalization can be catalysed with high product yields under oxygen-free and acceptorless conditions via inner-sphere atom abstraction by binuclear platinum(ii) diphosphite complexes. Both alcohols (51 examples), particularly the aliphatic ones, and saturated N-heterocycles (24 examples) can be efficiently dehydrogenated under light irradiation at room temperature. Regeneration of the photocatalyst by means of reductive elimination of dihydrogen from the in situ formed platinum(iii)-hydride species represents an alternative paradigm to the current approach in photoredox catalysis.

Switchable regioselection of C-H thiolation of indoles using different TMS counterions

A switchable regioselectivity in C-H thiolation reaction by simply swapping the counteranions of TMS is reported here for the first time. An exclusive C3-H thiolation of indoles with sodium arylsulfinates was achieved in the presence of TMSCl as a promoter. In contrast, with the use of TMSOTf instead of TMSCl under otherwise identical conditions, a regiospecific C2-H thiolation of indoles was realized with the same set of substrates.