Home Chemistry Heterocyclic Building Blocks Indoles 1H-Indole-2-Carbaldehyde
Aldol Condensation: The aldehyde group in can undergo aldol condensation reactions with other carbonyl compounds, leading to the formation of β-hydroxy carbonyl compounds.
Nucleophilic Addition: The indole ring and the carbonyl group can both act as nucleophilic sites. Nucleophiles, such as amines or hydrazines, can react with the carbonyl carbon or the indole ring to form imines or adducts.
Reduction: The aldehyde group can be reduced to an alcohol using reducing agents such as sodium borohydride or lithium aluminum hydride.
Mannich Reaction: The indole-2-carbaldehyde can participate in Mannich reactions, where it reacts with formaldehyde and a secondary amine to form β-amino carbonyl compounds.
Vilsmeier-Haack Reaction: It can react with the Vilsmeier-Haack reagent (a combination of phosphorus oxychloride and dimethylformamide) to form an α,β-unsaturated iminium ion, which can further react with nucleophiles.
Fischer Indole Synthesis: Under certain conditions, 1H-indole-2-carbaldehyde can undergo Fischer indole synthesis, especially if treated with an acid catalyst, leading to the formation of indole derivatives.
Oxidation: The aldehyde group can be oxidized to a carboxylic acid under specific conditions, using oxidizing agents such as potassium permanganate or chromic acid.
Reactions with Grignard Reagents: The indole-2-carbaldehyde can react with Grignard reagents to form alcohol derivatives.
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Methyl 2-formyl-1H-indole-5-carboxylate
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