Chemistry Heterocyclic Building Blocks Indoles 2,3-Dimethyl-1H-Indole

2,3-Dimethyl-1H-Indole

These compounds have the same murcko framework: 2,3-dimethyl-1H-indole

Electrophilic Aromatic Substitution (EAS): Indoles, being aromatic compounds, are susceptible to electrophilic aromatic substitution reactions. This involves the attack of an electrophile on the aromatic ring. Common electrophiles include acyl groups, alkyl halides, and nitro groups.
Nucleophilic Aromatic Substitution (SNAr): Indoles can also undergo nucleophilic aromatic substitution reactions. Nucleophiles can attack the indole ring under appropriate conditions.
Friedel-Crafts Acylation/Alkylation: Indoles can participate in Friedel-Crafts acylation and alkylation reactions when treated with acylating or alkylating agents in the presence of a Lewis acid catalyst.
Reduction: The indole ring can be reduced under certain conditions. For example, catalytic hydrogenation can reduce the double bond in the indole ring.
Oxidation: Indoles can be oxidized under specific conditions, leading to the formation of oxindole derivatives. Common oxidizing agents include peroxides or metal-based reagents.
Substitution at Methyl Groups: The methyl groups on positions 2 and 3 may undergo substitution reactions under appropriate conditions. For example, they could be replaced by other functional groups.
Diazo Coupling: Indoles can react with diazonium salts to form azo compounds through a diazo coupling reaction.
Metalation: The indole ring can be metalated at various positions, allowing for further functionalization through reactions with electrophiles.
N-Heterocyclic Carbene (NHC) Formation: Indoles can react with appropriate reagents to form N-heterocyclic carbenes, which can then participate in various catalytic processes.

Further Reading:

Framework+−

(1-(Tert-Butoxycarbonyl)-1H-Indol-2-Yl)Boronic Acid (1H-Indol-2-Yl)Boronic Acid (1H-Indol-2-Yl)Methanol (3As,7As)-Octahydro-1H-Indole (9H-Fluoren-9-Yl)Methyl (2-(1H-Indol-3-Yl)Ethyl)Carbamate 1,2,3,4-Tetrahydrocyclopenta[B]Indole 1,2-Dimethyl-1H-Indole 1-(1H-Indol-1-Yl)Ethan-1-One 1-(1H-Indol-3-Yl)Ethan-1-One 1-(Phenylsulfonyl)-1H-Indole 1-(Triisopropylsilyl)-1H-Pyrrolo[2,3-B]Pyridine 1-Benzyl-1H-Indole 1-Ethyl-1H-Indole 1-Methyl-1H-Indole 1-Methyl-1H-Indole-2-Carboxylic Acid 1-Methyl-1H-Indole-3-Carbaldehyde 1-Methyl-1H-Pyrrolo[2,3-B]Pyridine 1-Phenyl-1H-Indole 1H-Indol-3-Ol 1H-Indol-3-Yl Acetate 1H-Indol-4-Amine 1H-Indol-4-Ol 1H-Indol-5-Ol 1H-Indol-6-Amine 1H-Indol-6-Ol 1H-Indol-7-Amine 1H-Indole-2-Carbaldehyde 1H-Indole-2-Carbonitrile 1H-Indole-3-Carbonitrile 1H-Indole-3-Carboxylic Acid 1H-Indole-4-Carboxylic Acid 1H-Indole-5-Carbonitrile 1H-Indole-5-Carboxylic Acid 1H-Indole-6-Carbonitrile 1H-Indole-6-Carboxylic Acid 1H-Indole-7-Carbonitrile 1H-Indole-7-Carboxylic Acid 1H-Pyrrolo[2,3-B]Pyridine-3-Carbaldehyde 1H-Pyrrolo[2,3-B]Pyridine-5-Carbaldehyde 2,3,4,5-Tetrahydro-1H-Pyrido[4,3-B]Indole 2,3,4,9-Tetrahydro-1H-Pyrido[3,4-B]Indole 2,3-Dimethyl-1H-Indole 2-(1,3,2-Dioxaborolan-2-Yl)-1-Methyl-1H-Indole 2-(1H-Indol-1-Yl)Acetic Acid 2-(1H-Indol-3-Yl)Acetic Acid 2-(1H-Indol-3-Yl)Ethan-1-Amine 2-(1H-Indol-3-Yl)Ethan-1-Ol 2-(2-Methyl-1H-Indol-3-Yl)Acetic Acid 2-(4-Fluorophenyl)-1H-Indole 2-Methyl-1H-Indole-3-Carbaldehyde 2-Methyl-1H-Pyrrolo[2,3-B]Pyridine 3-(1-Oxoisoindolin-2-Yl)Piperidine-2,6-Dione 3-(1H-Indol-3-Yl)Propanoic Acid 3-(Piperidin-4-Yl)-1H-Indole 3-Iodo-1H-Pyrrolo[2,3-B]Pyridine 3-Methyl-1H-Indole 3H-Indole 4-Bromo-1H-Indole 4-Chloro-1H-Indole 4-Fluoro-1H-Indole 4-Fluoro-1H-Pyrrolo[2,3-B]Pyridine 4-Fluoroindoline-2,3-Dione 4-Methoxy-1H-Indole 4-Methyl-1H-Indole 4-Nitro-1H-Indole 5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)-1H-Indole 5-(Benzyloxy)-1H-Indole 5-Bromo-1-Methyl-1H-Indole 5-Chloro-1H-Indole 5-Chloro-1H-Indole-2-Carboxylic Acid 5-Chloro-1H-Pyrrolo[2,3-B]Pyridine 5-Fluoro-1H-Indole 5-Fluoro-1H-Pyrrolo[2,3-B]Pyridine 5-Fluoroindolin-2-One 5-Methoxy-1H-Indole 5-Methoxy-2-Methyl-1H-Indole 5-Methyl-1H-Indole 5-Nitro-1H-Indole 6-(Trifluoromethyl)-1H-Indole 6-Bromo-1-Methyl-1H-Indole 6-Bromo-1H-Indole 6-Bromo-1H-Pyrrolo[2,3-B]Pyridine 6-Chloro-1H-Indole 6-Chloro-1H-Pyrrolo[2,3-B]Pyridine 6-Fluoro-1H-Indole 6-Methoxy-1H-Indole 6-Methyl-1H-Indole 6-Methyl-1H-Pyrrolo[2,3-B]Pyridine 6-Nitro-1H-Indole 7-Bromo-1H-Indole 7-Bromoindoline-2,3-Dione 7-Chloro-1H-Indole 7-Fluoro-1H-Indole 7-Fluoro-1H-Indole-2-Carboxylic Acid 7-Methoxy-1H-Indole 7-Methyl-1H-Indole 7-Nitro-1H-Indole 9H-Pyrido[3,4-B]Indole Benzo[Cd]Indol-2(1H)-One Ethyl 1H-Indole-3-Carboxylate Ethyl 5-Chloro-1H-Indole-2-Carboxylate Ethyl 5-Fluoro-1H-Indole-2-Carboxylate Ethyl 6-Chloro-1H-Indole-2-Carboxylate Ethyl 7-Chloro-1H-Indole-2-Carboxylate Methyl 1H-Indole-3-Carboxylate Methyl 1H-Indole-4-Carboxylate Methyl 1H-Indole-5-Carboxylate Methyl 1H-Indole-6-Carboxylate Methyl 1H-Indole-7-Carboxylate Methyl 2-(1H-Indol-3-Yl)Acetate N-(2-(1H-Indol-3-Yl)Ethyl)Acetamide Spiro[Indoline-3,4'-Piperidin]-2-One Tert-Butyl 1H-Indole-1-Carboxylate Tert-Butyl 1H-Pyrrolo[2,3-B]Pyridine-1-Carboxylate Tert-Butyl 2-(1,3,2-Dioxaborolan-2-Yl)-1H-Indole-1-Carboxylate Tert-Butyl 3-(Hydroxymethyl)-1H-Indole-1-Carboxylate Tert-Butyl 3-Bromo-1H-Indole-1-Carboxylate Tert-Butyl 3-Iodo-1H-Indole-1-Carboxylate Tert-Butyl 5-Methoxy-1H-Indole-1-Carboxylate Tryptophan

By Key Group+−

Aminoindole Azaindole Benzoindole Benzyloxyindole Biindolinylidene Bromo-Indole-Carboxylate Bromo-Indole-Carboxylic Acid Bromo-Indole-Carboxylic-Acid Bromo-Methyl-Indole Bromoindole Chlorindole-Carboxylic-Acid Chloro-Indole-Carboxylate Chloro-Methyl Indole Chloroindole Cyanoindole Dihydroindolo Dimethyl-Indole Dioxaborolan-Indole Dioxaborolan-Indole-Carboxylate Fluorindole-Carboxylic Acid Fluorindole-Carboxylic-Acid Fluoro-Indole-Carboxylate Fluoroindole Fluoromethyl-Indole Formyl-Indole-Carboxylate Formylindole Hydroxyindole Hydroxyisoindoline Hydroxymethy-Indole-Carboxylate Indol-Amine Indol-Methanamine Indol-Methanol Indol-One Indole-Boronic Acid Indole-Boronic Acid/Ester Indole-Boronic-Acid Indole-Carbonitrile Indole-Ethanol Indole-Ethylamine Indole-Hydrochloride Indole-Hydroxyl Indolecarboxylate Indolecarboxylic Iodo-Indole Isoindole Methoxy-Indole-Carboxylate Methoxy-Methyl-Indole Methoxyindole Methyl-Indole-Carboxylic-Acid Methyl-Nitro-Indole Methylindole Nitro-Indole-Carboxylate Nitroindole Phenyl-Indole Piperidine-Indole Pyridinoindole Pyrimido-Indole Trifluoromethyl-Indole

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