Home Chemistry Heterocyclic Building Blocks Pyrrolines 2,5-Dihydro-1H-Pyrrole
Electrophilic Aromatic Substitution (EAS): Like pyrrole, 2,5-dihydro-1H-pyrrole can undergo electrophilic aromatic substitution reactions. It can react with electrophiles (e.g., acyl chlorides or nitroarenes) in the presence of Lewis acids to introduce substituents onto the aromatic ring.
Nucleophilic Addition: 2,5-dihydro-1H-pyrrole can undergo nucleophilic addition reactions at the C2 position. For example, it can react with electrophiles such as alkyl halides to form substituted derivatives.
Oxidation: 2,5-dihydro-1H-pyrrole can be oxidized to pyrrole using mild oxidizing agents like oxygen or stronger oxidizing agents like chromic acid. This reaction involves the conversion of the C2-C5 double bond to a nitrogen-containing pyrrole ring.
Reduction: The compound can be reduced to the corresponding dihydropyrrole using reducing agents like hydrogen gas and a metal catalyst.
Ring Opening: In some cases, the ring can be opened under specific reaction conditions, leading to the formation of linear or branched compounds. This typically involves breaking one of the C-N bonds in the ring.
Alkylation and Acylation: 2,5-dihydro-1H-pyrrole can be alkylated or acylated at the nitrogen atom to introduce alkyl or acyl groups, respectively.
Cyclization Reactions: It can participate in various cyclization reactions to form more complex heterocyclic compounds when combined with appropriate reagents.
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(S)-tert-Butyl 2-(hydroxymethyl)-2,5-dihydro-1H-pyrrole-1-carboxylate
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tert-Butyl 4-cyano-3-hydroxy-2,2-dimethyl-2,5-dihydro-1H-pyrrole-1-carboxylate
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tert-Butyl 3-(trifluoromethyl)-2,5-dihydro-1H-pyrrole-1-carboxylate
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Ethyl N-Boc-2,5-dihydropyrrole-3-carboxylate
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tert-Butyl 3-amino-4-cyano-2,5-dihydro-1H-pyrrole-1-carboxylate
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tert-Butyl 3-(((trifluoromethyl)sulfonyl)oxy)-2,5-dihydro-1H-pyrrole-1-carboxylate
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tert-Butyl 2,5-dihydro-1H-pyrrole-1-carboxylate
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1-(tert-Butoxycarbonyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid
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(R)-1-tert-butyl 2-methyl 1H-pyrrole-1,2(2H,5H)-dicarboxylate
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