Tetrahedron

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

R Torregrosa, IM Pastor, M Yus

Index: Torregrosa, Rosario; Pastor, Isidro M.; Yus, Miguel Tetrahedron, 2005 , vol. 61, # 47 p. 11148 - 11155

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Citation Number: 38

Abstract

2-Lithioimidazole was prepared by means of a new protocol, which consists of a slight excess of lithium metal in the presence of a substoichiometric amount of isoprene (20mol%) in THF at room temperature. By reacting this organolithium with carbonyl electrophiles 2- (hydroxyalkyl) imidazoles were obtained, in good yields. As a result of the reaction of the mentioned lithium intermediate with imines, the corresponding 2-(aminoalkyl) imidazoles ...