Chemistry
Heterocyclic Building Blocks
Azetidines
1-benzylazetidine
Nucleophilic Substitution: 1-Benzylazetidine can undergo nucleophilic substitution reactions at the nitrogen atom. For example, it can react with strong nucleophiles like hydride ions (H-) to form the reduced product, N-benzylpiperidine.
Acid-Catalyzed Hydrolysis: Under acidic conditions, the benzyl group can be cleaved from the azetidine ring, resulting in the formation of piperidine derivatives.
Base-Catalyzed Hydrolysis: Under basic conditions, the azetidine ring can undergo ring-opening reactions, leading to the formation of various products.
Reduction: 1-Benzylazetidine can be reduced using reducing agents like lithium aluminum hydride (LiAlH4) to form N-benzylamine.
Acylation: The nitrogen atom in 1-benzylazetidine can be acylated with acyl chlorides or anhydrides to introduce acyl groups onto the nitrogen atom.
N-Oxidation: The nitrogen atom can be oxidized to form N-oxide derivatives under appropriate conditions.
Halogenation: The benzyl group in 1-benzylazetidine can undergo halogenation reactions (e.g., chlorination or bromination) in the presence of halogenating agents.
Ring-Opening Reactions: Depending on the reagents and conditions, the azetidine ring can undergo ring-opening reactions to form various open-chain compounds.
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tert-Butyl (1-benzylazetidin-3-yl)carbamate
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(1-Benzylazetidin-3-yl)methanamine dihydrochloride