Chemistry
Heterocyclic Building Blocks
Indoles
1-methyl-1H-indole
Electrophilic Aromatic Substitution (EAS): Indoles are known for their reactivity in EAS reactions. The electron-rich nature of the aromatic ring makes them susceptible to electrophilic attack. The reaction typically occurs at the 2- or 3-position of the indole ring due to the presence of a nitrogen lone pair.
Nucleophilic Substitution: The nitrogen atom in the indole ring can act as a nucleophile, participating in nucleophilic substitution reactions with electrophiles.
Alkylation and Acylation: The nitrogen atom in the indole ring can be alkylated or acylated under appropriate conditions, leading to the formation of N-alkyl or N-acyl indole derivatives.
Friedel-Crafts Reactions: Indoles can undergo Friedel-Crafts acylation or alkylation reactions when treated with appropriate acylating or alkylating agents in the presence of a Lewis acid catalyst.
Reduction: The double bond in the 1-methyl-1H-indole could potentially undergo reduction, depending on the reaction conditions. This could yield a saturated derivative of the indole ring.
Oxidation: Indoles can be oxidized under certain conditions, leading to the formation of oxindoles or other oxidized products.
Mannich Reaction: The nitrogen in the indole ring can participate in the Mannich reaction, where it reacts with formaldehyde and a secondary amine to form a β-amino carbonyl compound.
Hofmann Rearrangement: Under specific conditions, the nitrogen in the indole ring can undergo Hofmann rearrangement, resulting in the migration of the nitrogen to a different position in the ring.
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2,2,2-Trifluoro-1-(1-methyl-1H-indol-3-yl)ethan-1-ol
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N-Methyl-1-(1-methyl-1H-indol-2-yl)methanamine
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Potassium trifluoro(1-methylindol-2-yl)borate
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1-Methyl-5-(trifluoromethyl)-1H-indole
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1-Methyl-1H-indole-4-sulfonyl chloride
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6-Methoxy-1-methyl-1H-indole-3-carbaldehyde