Tetrahedron letters

A concise and optimized four-step approach toward 2-(aryl-) alkylsulfanyl-, 4 (5)-aryl-, 5 (4)-heteroaryl-substituted imidazoles using alkyl-or arylalkyl thiocyanates

SA Laufer, AJ Liedtke

Index: Laufer, Stefan A.; Liedtke, Andy J. Tetrahedron Letters, 2006 , vol. 47, # 40 p. 7199 - 7203

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Citation Number: 17

Abstract

A convenient cyclization method leading to trisubstituted imidazoles in up to 84% yield is reported. Diverse 1-aryl-, 2-heteroaryl-substituted ethanones are converted into the corresponding α-oximino derivatives which are reduced under regioselective conditions. The obtained α-amino carbonyl intermediates are reacted with alkyl-or arylalkyl thiocyanates to directly yield C2–S-substituted imidazoles.