23543-66-0

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 63, p. 7652, 1998 DOI: 10.1021/jo9803277Tetrahedron Letters, 28, p. 5291, 1987 DOI: 10.1016/S0040-4039(00)96710-8

InChI:InChI=1/C11H11NO/c1-8-7-12(9(2)13)11-6-4-3-5-10(8)11/h3-7H,1-2H3

Upstream product

• 83-34-1 3-Methylindole 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 201230-82-2 carbon monoxide 
• 29124-68-3 N-(2-vinylphenyl)acetamide 

Downstream Products

• 78388-92-8 1-(3-methyl-2-phenyl-1H-indol-1-yl)ethan-1-one 
• 83-34-1 3-Methylindole 
• 36797-43-0 3-methyl-N-(p-toluenesulfonyl)indole 
• 727416-63-9 (R)-3-methyl-1-(p-toluenesulfonyl)indoline 
• 727416-57-1 (S)-(+)-3-methyl-N-(p-toluenesulfonyl)indoline 
• 1504-06-9 3-methylindolin-2-one 
• 1441174-23-7 N-acetyl-3-(2-hydroxy-5-methylphenyl)-3-methylindoline 
• 1441173-82-5 N-acetyl-3-(4-hydroxyphenyl)-3-methylindoline 
• 1441174-25-9 C₂₀H₂₃NO₂ 
• 1441173-84-7 C₁₈H₁₉NO₂ 
• 1441174-27-1 C₂₀H₂₃NO₂ 
• 1441174-29-3 C₂₄H₂₃NO₂ 
• 1441174-31-7 C₁₉H₂₁NO₂ 
• 1441174-33-9 C₁₇H₁₆FNO₂ 

Relevant academic research and scientific papers

Reactions of N-Acylated Indoles with Singlet Oxygen

Reactions of seven N-acyl indole derivatives with singlet oxygen have been investigated. 1-Acetyl-(1a) and 1-(chloroacetyl)-2,3-dimethylindole (1b) gave exclusively 1-acetyl- (2a) and 1-(chloroacetyl)-2-hydroperoxy-3-methyleneindoline (2b), respectively, in high yields via ene reaction on irradiation with oxygen in the presence of TPP sensitizer. 1-Acetyl-3-methylindole (1c) gave only 1-acetyl-2-hydroperoxy-3-methyleneindoline (2c) in low yield under the same conditions.In contrast, 1-acetyl-2-methyl-3-ethylindole (3a) and 1-acetyl-2-methyl-3-isopropylindole (3b) gave a mixture of ene products, 2-hydroperoxy- and 3-hydroperoxyindolines (4a and b and 5a and b), in addition to 2,3-bond cleavage products 6a and 6b, respectively.In the case of 1-acetyl-2-methyl-3-tert-butylindole (7), only the product of 2,3-bond cleavage (8) was obtained.A 1,2-dioxetane is intermediate in the cleavage and could be observed after photooxygenation of 7 at -5 deg C by NMR and was reduced by trimethylphosphite and dimethyl sulfide.The decomposition rate constant of 1,2-dioxetane 10 was measured by NMR; Ea is 24.6 kcal/mol.

Interrupted Intramolecular Hydroaminomethylation of N-Protected-2-vinyl Anilines: Novel Access to 3-Substitued Indoles or Indoline-2-ols

A new synthetic alternative to the synthesis of 3-methyl indoles and 3-methyl indoline-2-ols with an excellent atomic economy is presented in this study. It is demonstrated that the intramolecular interrupted hydroaminomethylation (HAM) reaction is a powerful tool for the formation of these compounds, which exhibit wide-ranging biological activity. Several N-Protected-2-vinyl anilines were synthesized and involved in the reaction producing the corresponding 3-methylindole or 3-methyl indoline-2-ol depending on the nature of the N-protecting groups.

Metal-Free C-O Bond Functionalization: Catalytic Intramolecular and Intermolecular Benzylation of Arenes

A catalytic, metal-free intramolecular rearrangement of benzyl phenyl ethers using nitrosonium salt as a catalyst is described. The optimized reaction conditions enabled a catalytic and metal-free Friedel-Crafts alkylation reaction with benzylic alcohols, producing water as the stoichiometric byproduct. A comprehensive scope (>50 examples) for both approaches and application in drug synthesis were demonstrated. Mechanistic studies suggest a Lewis acid-based mechanism for the metal-free Friedel-Crafts reaction.

Sulfated Zirconia: An Efficient and Reusable Heterogeneous Catalyst in the Friedel–Crafts Acylation Reaction of 3-Methylindole

Abstract: An efficient process for the Friedel–Crafts acylation of 3-methylindole with acid anhydrides in the presence of sulfated zirconia was developed. This catalyst shows excellent catalytic activity with good conversion and selectivity towards formation of the products of 2-acylation (3-methyl-1H-indol-2-yl)ketones. Other advantages related to this process are the simple work-up procedure and smaller production of chemical waste. The catalyst was easily recycled and reused with a minimal loss in activity through three reaction cycles. The catalyst was characterized by FT-IR spectroscopy, X-Ray diffraction and superficial acidity. Graphical Abstract: [Figure not available: see fulltext.].

Lewis Acid and Fluoroalcohol Mediated Nucleophilic Addition to the C2 Position of Indoles

Indole readily undergoes nucleophilic substitution at the C3 site, and many indole derivatives have been functionalized using this property. Indole also forms indolium, which allows electrophilic addition in acidic conditions, but current examples have been limited to intramolecular reactions. C2 site-selective nucleophilic addition to indole derivatives using fluoroalcohol and a Lewis acid was developed.

Regioselective hydroarylation reactions of C3 electrophilic N-acetylindoles activated by FeCl3: An entry to 3-(Hetero)arylindolines

A method for the direct and rare umpolung of the 3 position of indoles is reported. The activation of N-acetylindole with iron(III) chloride allows the C-H addition of aromatic and heteroaromatic substrates to the C2-C3 double bond of the indole nucleus to generate a quaternary center at C3 and leads regioselectively to 3-arylindolines. Optimization, scope (50 examples), practicability (gram scale, air atmosphere, room temperature), and mechanistic insights of this process are presented. Synthetic transformations of the indoline products into drug-like compounds are also described.

Direct oxidative coupling of N-acetyl indoles and phenols for the synthesis of benzofuroindolines related to phalarine

Inspired by the biogenetic synthesis of benzofuro-indoline-containing natural products, we designed an oxidative coupling between phenol and N-acetyl indoles. This straightforward and direct radical process, mediated by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and FeCl 3 allowed the regioselective synthesis of benzofuro[3,2-b]indolines, whose structure is found in the natural product phalarine.

Ir(I)-catalyzed C-H bond alkylation of C2-position of indole with alkenes: Selective synthesis of linear or branched 2-alkylindoles

A cationic iridium-catalyzed C2-alkylation of N-substituted indole derivatives with various alkenes has been developed, which selectively gives linear or branched 2-alkylindoles in high to excellent selectivity. This protocol relies on the use of the carbonyl group on the nitrogen atom of indole as a directing group: a linear product was predominant when an acetyl group was used as a directing group, and a branched product was predominant with a benzoyl group.

Ir(I)-catalyzed C-H bond alkylation of C2-position of indole with alkenes: Selective synthesis of linear or branched 2-alkylindoles

A cationic iridium-catalyzed C2-alkylation of N-substituted indole derivatives with various alkenes has been developed, which selectively gives linear or branched 2-alkylindoles in high to excellent selectivity. This protocol relies on the use of the carbonyl group on the nitrogen atom of indole as a directing group: a linear product was predominant when an acetyl group was used as a directing group, and a branched product was predominant with a benzoyl group.

Enantioselective cyclopropanation of indoles: Construction of all-carbon quaternary stereocenters

The first enantioselective copper-catalyzed cyclopropanation of N-acyl indoles is described. Using carbohydrate-based bis(oxazoline) ligands (glucoBox), the products were obtained in up to 72% ee. Cyclopropanation of N-Boc 3-methyl indole yielded a product with an all-carbon quaternary stereocenter, which is a valuable building block for the synthesis of indole alkaloids: Deprotection and rearrangement gave a tricyclic hemiaminal ester in 96% ee, which was subsequently employed as a key intermediate for the synthesis of (-)-desoxyeseroline.