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Synthesis 1992; 1992(7): 645-647
DOI: 10.1055/s-1992-26187
short paper
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Preparation of 2-Substituted 3-Hydroxypyridines and Direct Conversion of 2-Furyl Ketone into a Perhydroazulene

Steven M. Bromidge* , David A. Archer, Peter G. Sammes
  • *School of Chemistry, University of Leeds, Leeds, LS2 9JT, England
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Publication Date:
17 September 2002 (online)

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2-Acylfurans can be converted directly into 2-substituted 3-hydroxypyridines by heating them with ammonia; 2-acylpyrroles and 3-aminopyridines are formed as byproducts in this rearrangement. Using propylamine in place of ammonia, 1-(2-furyl)-5-methylhex-5-en-1-one (8) could be rearranged to give the aza-bridged perhydroazulenone (5-methyl-10-oxo-11-propyl-11-azatricyclo-[5.3.1.01,5]undec-8-ene, 10).