Home Chemistry Heterocyclic Building Blocks Tetrahydroquinolines 5,6,7,8-Tetrahydroquinoline
Aromatic Substitution: The nitrogen atom in the quinoline ring can undergo electrophilic aromatic substitution reactions, similar to other aromatic compounds. For example, you can perform nitration (adding a nitro group), halogenation (adding halogen atoms), or alkylation/acylation reactions.
Reduction: The hydrogen atoms in the tetrahydroquinoline ring can be further reduced, for example, using a reducing agent like sodium borohydride (NaBH4) to convert it into a saturated piperidine ring.
Alkylation: You can alkylate the nitrogen atom in the quinoline ring using alkyl halides, resulting in the formation of quaternary ammonium salts.
Oxidation: The hydrogen atoms in the tetrahydroquinoline ring can be oxidized to convert it back into the quinoline ring. Oxidizing agents like potassium permanganate (KMnO4) can be used for this purpose.
Cyclization: Depending on the reaction conditions and reagents, you can induce cyclization reactions within the tetrahydroquinoline ring to form other heterocyclic compounds.
Heterocyclic Reactions: The nitrogen atom in the quinoline ring can participate in various heterocyclic reactions, such as the Hantzsch synthesis, which involves the formation of dihydropyridines.
Functional Group Reactions: If there are other functional groups (e.g., alkyl, alkoxy, amino, etc.) attached to the tetrahydroquinoline ring, they can undergo various reactions specific to those functional groups. For example, amine groups can undergo acylation or alkylation reactions, while hydroxy groups can undergo esterification or etherification.
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4-Nitro-5,6,7,8-tetrahydroquinoline 1-oxide
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N-Methyl-5,6,7,8-tetrahydroquinoline-8-carboxamide
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2-Chloro-6-methyl-3-nitro-5,6,7,8-tetrahydroquinoline
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(R)-5,6,7,8-Tetrahydroquinolin-8-amine hydrochloride
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