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

摘要

A convenient cyclization method leading to trisubstituted imidazoles in up to 84% yield is reported. Diverse 1-aryl-, 2heteroaryl-substituted ethanones are converted into the corresponding alpha-oximino derivatives which are reduced under regioselective conditions. The obtained alpha-amino carbonyl intermediates are reacted with alkyl- or arylalkyl thiocyanates to directly yield C-2-S-substituted imidazole. (c) 2006 Elsevier Ltd. All rights reserved.