Home Chemistry Heterocyclic Building Blocks Indoles 3-Methyl-1H-Indole
Electrophilic Aromatic Substitution (EAS): Indoles are known for their reactivity in electrophilic aromatic substitution reactions. The electron-rich nature of the aromatic ring makes it susceptible to attack by electrophiles. This reaction can lead to the introduction of substituents onto the indole ring.
Nucleophilic Aromatic Substitution (SNAr): The nitrogen atom in the indole ring can act as a nucleophile, participating in nucleophilic aromatic substitution reactions with suitable electrophiles.
Friedel-Crafts Acylation/Alkylation: Indoles can undergo Friedel-Crafts reactions where acyl or alkyl groups are introduced onto the indole ring in the presence of a Lewis acid catalyst.
Reduction: The double bond in the five-membered ring of indole can be reduced under appropriate conditions, leading to the formation of dihydroindole.
Oxidation: Indoles can be oxidized to form oxindoles under certain conditions. Oxidation may occur at various positions on the indole ring.
Metalation: The C-H bond at the 3-position of the indole ring can be deprotonated by a strong base, leading to metalation. This metalated species can then react with various electrophiles.
Condensation Reactions: The nitrogen atom in the indole ring can participate in condensation reactions, such as Mannich or Fischer indole syntheses, where it reacts with carbonyl compounds or imines.
N-Heterocyclic Carbene Formation: The C-H bond at the 3-position of the indole ring can be activated, leading to the formation of an N-heterocyclic carbene under certain conditions.
Arylation: The aromatic ring can undergo arylation reactions, where it reacts with aryl halides or other aryl electrophiles.
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Ethyl 5-chloro-3-methyl-1H-indole-2-carboxylate
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5-Bromo-3-methyl-1H-indole-7-carbonitrile
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C-(2,3-Dimethyl-1H-indol-5-yl)-methylamine
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Methyl 2,3-dimethyl-1H-indole-5-carboxylate
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2,3-Dimethyl-1H-indole-5-carboxylic acid
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7-Chloro-3-methyl-1H-indole-2-carboxylic acid
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(5-Chloro-3-methyl-1H-indol-2-yl)methanol
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