Home Chemistry Heterocyclic Building Blocks Oxazolidines Oxazolidine
Ring Opening: Oxazolidines can undergo ring-opening reactions, typically in the presence of strong nucleophiles or acids. For example, treatment with a strong nucleophile, such as sodium amide (NaNH2), can lead to the cleavage of the oxazolidine ring to form an amine and an alcohol.
Hydrolysis: Oxazolidines can be hydrolyzed by exposure to water or acidic conditions. This reaction results in the formation of the corresponding amine and alcohol, as the ring is cleaved by the hydrolyzing agents.
Acylation: Oxazolidines can be acylated using acyl chlorides or anhydrides to form N-acyloxazolidines. This reaction involves the substitution of the hydrogen atom on the nitrogen with an acyl group.
Nucleophilic Addition: Oxazolidines can participate in nucleophilic addition reactions, where a nucleophile attacks the carbonyl group adjacent to the oxazolidine ring, forming a new bond.
Alkylation: Oxazolidines can be alkylated by treatment with alkyl halides or other alkylating agents. This reaction can introduce alkyl groups onto the nitrogen atom, leading to N-alkyloxazolidines.
Cyclization: Oxazolidines can participate in intramolecular cyclization reactions to form heterocyclic compounds. This often involves the reaction of the oxygen atom in the oxazolidine ring with another functional group within the molecule.
Rearrangement: Under certain conditions, oxazolidines can undergo rearrangement reactions, leading to the formation of different products. These rearrangements often involve migration of atoms or groups within the molecule.
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tert-Butyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate
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(R)-N-Boc-2,2-dimethyl-4-vinyloxazolidine
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tert-Butyl 4-acetyl-2,2-dimethyloxazolidine-3-carboxylate
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(R)-tert-Butyl 4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate
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(S)-3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde
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(S)-3-Boc-4-(Methoxymethylcarbamoyl)-2,2-dimethyloxazolidine
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(S)-N-Boc-4-(2-hydroxyethyl)-2,2-dimethyloxazolidine
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(R)-tert-Butyl 4-(bromomethyl)-2,2-dimethyloxazolidine-3-carboxylate
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(R)-tert-Butyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate
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(S)-tert-Butyl 2,2-dimethyl-4-vinyloxazolidine-3-carboxylate
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Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate
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(S)-3-tert-Butoxycarbonyl-4-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine
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(2S,4R)-3-tert-Butyl 4-methyl 2-tert-butyloxazolidine-3,4-dicarboxylate
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