Home Chemistry Heterocyclic Building Blocks Indoles 3H-Indole
Electrophilic Aromatic Substitution: Indole is highly reactive toward electrophilic aromatic substitution reactions. Substitution can occur at positions 2, 3, and 7 of the indole ring.
Nucleophilic Substitution: Indole can undergo nucleophilic substitution reactions at the C3 position or at the nitrogen atom in the pyrrole ring.
Friedel-Crafts Acylation and Alkylation: Indole can be acylated or alkylated using Friedel-Crafts reactions.
Vilsmeier-Haack Reaction: This reaction can be used to introduce formyl groups onto the indole ring.
Metalation Reactions: Indole can be deprotonated at various positions to form metalated intermediates. For example, treatment with strong bases like LDA (lithium diisopropylamide) can result in metalation at the C3 position.
Grignard Reactions: Indole can react with Grignard reagents to form various derivatives.
Hofmann Rearrangement: The nitrogen atom in indole can be transformed into an isocyanide group through the Hofmann rearrangement.
Substitution at Nitrogen Atom: The nitrogen atom in indole can undergo various reactions, including alkylation, acylation, and deprotonation.
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3,3-Dimethyl-3H-indole-4-carboxylic acid
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Potassium 2,3,3-trimethyl-3H-indole-5-sulfonate
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