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Isoprene-catalyzed lithiation of imidazole: synthesis of 2-(hydroxyalkyl)- and 2-(aminoalkyl)imidazoles

Rosario Torregrosa, Isidro M. Pastor and Miguel Yus*

*Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain, Email:

R. Torregrosa, I. M. Pastor, M. Yus, Tetrahedron, 2005, 61, 11148-11155.

DOI: 10.1016/j.tet.2005.09.024


2-Lithioimidazole was prepared using lithium metal in the presence of a catalytic amount of isoprene in THF at room temperature. By reacting this organolithium compound with carbonyl electrophiles 2-(hydroxyalkyl)imidazoles and 2-(aminoalkyl)imidazoles were obtained in good yields.

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Key Words

Imidazoles, Isoprene-catalyzed lithiation, Carbonyl compounds, Imines, Deprotonation, Lithium

ID: J72-Y2005-3160