Home Chemistry Heterocyclic Building Blocks Quinolines 1,2-Dihydroquinoline
Aromatic Electrophilic Substitution: Like other aromatic compounds, 1,2-dihydroquinoline can undergo electrophilic aromatic substitution reactions. For example, it can react with strong electrophiles like nitration (using concentrated nitric acid) or halogenation (using halogens or Lewis acids) to introduce substituents onto the aromatic ring.
Alkylation and Acylation: 1,2-dihydroquinoline can undergo alkylation and acylation reactions, where alkyl or acyl groups are added to the nitrogen atom or the aromatic ring. This can be achieved using appropriate alkyl halides or acyl halides in the presence of a base.
Reduction: Reduction reactions can be used to convert 1,2-dihydroquinoline into the corresponding 1,2,3,4-tetrahydroquinoline. Common reducing agents like hydrogen gas (catalytic hydrogenation) or metal hydrides can be employed for this purpose.
Cyclization Reactions: 1,2-Dihydroquinoline can participate in various cyclization reactions to form different heterocyclic compounds. For example, it can undergo N-alkylation followed by cyclization to form quinolines.
Functional Group Transformations: Various functional group transformations can be carried out on 1,2-dihydroquinoline, depending on the specific functional groups present. Reactions like amine reactions, amide formation, and more are possible.
Heterocycle Formation: 1,2-Dihydroquinoline can be used as a starting material to synthesize other heterocyclic compounds. For instance, it can react with appropriate reagents to form compounds containing fused rings, such as quinolizidines or isoquinolines.
Reductive Amination: The amino group in 1,2-dihydroquinoline can participate in reductive amination reactions, where it can be converted to a variety of amine derivatives by reacting with aldehydes or ketones in the presence of reducing agents.
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7-Methoxy-2,2,4-trimethyl-1,2-dihydroquinoline
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Isobutyl 2-isobutoxyquinoline-1(2H)-carboxylate
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