Preparation of 2-Substituted 3-Hydroxypyridines and Direct Conversion of 2-Furyl Ketone into a Perhydroazulene

Abstract
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).

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