Investigation of 1-bromo-3-buten-2-one as building block in organic synthesis

1-Bromo-3-buten-2-one is investigated as a building block for organic synth esis. Reduction to the corresponding alcohol works best with lithium alumin ium hydride, reaction with primary amines gives 5-membered-aza-heterocycles in moderate yields and reaction with activated methylene compounds to form 5-membered-carbocycles gave unsatisfactory yields when a one-pot-procedure was used. The first step of a stepwise protocol, a Michael addition, is di scussed. (C) 2001 Elsevier Science Ltd. All rights reserved.