1496-76-0

Usage

Compound class

Substituted indoles.

Structure

Bicyclic ring system consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Potential applications

Medicinal chemistry, pharmaceuticals, and organic synthesis.

Usage

Versatile building block for the synthesis of complex organic molecules in drug discovery and development.

Safety precautions

Handle with care, as it may have hazardous properties.

Upstream product

• 120-72-9 indole 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 74422-06-3 cis-3-benzoyl-2a,7b-dihydro-3H-cyclobutindole 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 55-21-0 benzamide 
• 4231-62-3 1-benzoyl-1H-benzotriazole 
• 591-50-4 iodobenzene 
• 13939-06-5 molybdenum hexacarbonyl 
• 10364-94-0 1-benzoylimidazole 
• 496-15-1 1-indoline 
• 1374822-89-5 (+/-)-1-(2-nitro-1-phenylethyl)indoline 
• 102-96-5 (2-nitroethenyl)benzene 
• 685110-52-5 N-(2-ethynylphenyl)benzamide 

Downstream Products

• 579-93-1 2-(Benzoylamino)benzoic Acid 
• 6299-36-1 1-benzoyl-3-bromo-indole 
• 87066-78-2 1-benzoyl-3-hydroxy-2-methoxyindole 
• 87066-78-2 cis-1-benzoyl-3-hydroxy-2-methoxyindoline 
• 87066-78-2 trans-1-benzoyl-3-hydroxy-2-methoxyindoline 
• 74786-89-3 Phenyl-acetic acid (2R,3S)-1-benzoyl-3-phenylacetoxy-2,3-dihydro-1H-indol-2-yl ester 
• 41823-60-3 cis-exo-1-acetoxy-3-benzoyl-1,2,2a,7b-tetrahydro-3H-cyclobutindole 
• 41823-60-3 endo-1-acetoxy-3-benzoyl-1,2,2a,7b-tetrahydro-3H-cyclobutindole 
• 135733-78-7 Phenyl-((2aS,7bR)-1,1,2,2-tetramethyl-1,2,2a,7b-tetrahydro-cyclobuta[b]indol-3-yl)-methanone 
• 136321-34-1 C₂₂H₂₃NO 
• 136321-34-1 C₂₂H₂₃NO 
• 135733-81-2 ((1R,2aS,7bS)-1-Cyclopropyl-1,2,2a,7b-tetrahydro-cyclobuta[b]indol-3-yl)-phenyl-methanone 
• 135733-80-1 Phenyl-(5aR,10aR)-6,9,10,10a-tetrahydro-5aH-cyclohepta[b]indol-5-yl-methanone 
• 109906-82-3 dimethyl 5H-pyridazino<4,5-b>indole-1,4-dicarboxylate 

Relevant academic research and scientific papers

Selective N1-Acylation of Indazoles with Acid Anhydrides Using an Electrochemical Approach

An electrochemical synthesis method for the selective N1-acylation of indazoles has been developed. This "anion pool" approach electrochemically reduces indazole molecules generating indazole anions and H2. Acid anhydrides are then introduced to the solution resulting in selective acylation of the N1-position of the indazoles. This procedure can also be applied to the acylation of benzimidazoles and indoles. The reaction can also be performed using a 9 V battery without loss of reaction efficiency.

Ring-Opening of Indoles: An Unconventional Route for the Transformation of Indoles to 1 H-Pyrazoles Using Lewis Acid

An unusual transformation of indoles to pyrazoles via an aromatic ring-opening strategy has been developed. The salient feature of this strategy involves the C2-N1 bond opening and concomitant cyclization reaction of the C2=C3 bond of the indole moiety with the tosylhydrazone, which proceeds under transition-metal and ligand free conditions. This ring-opening functionalization of indoles provides a wide scope of differently substituted pyrazoles.

An effective C-C double bond formation via Cu(I)-catalyzed dehydrogenation

A dehydrogenation method using Cu(I) and either N,N-di-tert-butylthiadiaziridine 1,1-dioxide or N,N-di-tert-butyldiaziridinone is reported. The dehydrogenation allows a facile introduction of C-C double bond(s) into various carbocycles and heterocycles such as oxazolines and thiazolines.

Na 2 CO 3-Catalyzed N-Acylation of Indoles with Alkenyl Carboxylates

The N-acylation of indoles has been accomplished via inorganic base catalysis. It provided an efficient and simple catalysis system for the preparation of N-acylindoles with alkenyl carboxylates as acylating agents. A broad variety of indoles undergo the smooth N-acylation using Na 2 CO 3 as catalyst in MeCN at 120? °C to give the corresponding N-acylindoles in good to excellent yields.

A new, stereoselective, ring-forming reaction of 1,2-ethanedithiol with N-acylated indoles

(Chemical Equation Presented) While attempting to prepare 2,5-dithiacyclopentyl derivatives from N-acyl 5-fluoroindole by reaction with 1,2-ethanedithiol we discovered that, instead of the expected product, annelation occurred to give a tricyclic compound containing a 3,6-dithiaazepine ring. This reaction is stereoselective and was found to be general for N-acylindoles, not being affected by substituents on the indole ring.

Trifluoromethylselenolation andN-acylation of indoles with [Me4N][SeCF3]

An efficient method for oxidative trifluoromethylselenolation/N-acylation of indoles with excess [Me4N][SeCF3] in the presence of acyl peroxides and their derivatives is described. The reaction is easy to handle, proceeds smoothly at room temperature under metal-free conditions, and shows advantages such as good functional group tolerance, excellent regioselectivity, and compatibility of a number of substrates, producing 1-acyl and 3-trifluoromethylselanyl substituted indoles in good yields. Acyl peroxides and peroxycarboxylic acid behave as both oxidants and acyl sources in the transformation. This one-pot procedure provides a convenient access to a new class of indole derivatives, representing the first trifluoromethylselanyl bifunctionalization of indoles with the nucleophilic [Me4N][SeCF3] reagent.

Photoredox Catalysis Induced Bisindolylation of Ethers/Alcohols via Sequential C-H and C-O Bond Cleavage

A visible-light-engaged 2-fold site-selective alkylation of indole derivatives with aliphatic ethers or alcohols has been accomplished for easy access to symmetric 3,3′-bisindolylmethane derivatives. The experimental data suggest a sequential photoredox catalysis induced radical addition and proton-mediated Friedel-Crafts alkylation mechanism.

Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides

Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.

Scaffold hopping by net photochemical carbon deletion of azaarenes

Discovery chemists routinely identify purpose-tailored molecules through an iterative structural optimization approach, but the preparation of each successive candidate in a compound series can rarely be conducted in a manner matching their thought process. This is because many of the necessary chemical transformations required to modify compound cores in a straightforward fashion are not applicable in complex contexts. We report a method that addresses one facet of this problem by allowing chemists to hop directly between chemically distinct heteroaromatic scaffolds. Specifically, we show that selective photolysis of quinoline N-oxides with 390-nanometer light followed by acid-promoted rearrangement affords N-acylindoles while showing broad compatibility with medicinally relevant functionality. Applications to late-stage skeletal modification of compounds of pharmaceutical interest and more complex transformations involving serial single-atom changes are demonstrated.

N-2-pyrimidyl-3-fluoroindole compound and preparation method and application thereof

The preparation method of the N-2-pyrimidinyl-3-fluoroindole compound shown in the formula (I) comprises the following steps: by taking an acetonitrile solvent as a reaction medium, adding the N-2-pyrimidinyl indole compound shown in the formula (III), se