Tetrahedron letters

A convenient synthesis of 1, 4-disubstituted imidazoles

Y He, Y Chen, H Du, LA Schmid, CJ Lovely

Index: He, Yong; Chen, Yingzhong; Du, Hongwang; Schmid, Lesley A.; Lovely, Carl J. Tetrahedron Letters, 2004 , vol. 45, # 28 p. 5529 - 5532

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Citation Number: 30

Abstract

An efficient method for the regioselective protection of 4-alkyl-, 4-iodo, 4-vinylimidazoles has been developed via an alkylation–isomerization sequence with various imidazole-protecting groups. The initially formed mixture of 4/5-alkyl-, 4/5-iodo, and 4/5-vinylimidazoles are isomerized to the corresponding 4-isomers on treatment of a DMF solution with a small amount of RX and heating at 75° C.