The chemistry of 1,5-diketone derivatives. 2. Preparation of 2-hydroxy-1,3,5-triphenyl-1,5-pentanedione and some heterocycle derivatives

The preparation of 2-hydroxy-1,3,5-triphenyl-1,5-pentanedione by the addition of -hydroxy- or -acetoxyacetophenone to chalcone is described. The 2-hydroxy-1,5-diketone obtained does not show a tendency to form an intramolecular hemi-acetal; instead, an acetate is formed. Reaction with hydroxylamine hydrochloride gives 3-aza-2,8-dioxa-1,4,6-triphenylbicyclo[3.2.1]oct-3-ene, and with ammonium acetate 2,4,6-triphenylpyridine and 3-amino-2,4,6-triphenylpyridine are formed. On reaction with p-toluenesulfonic acid the hydroxydiketone is converted into 3-oxo-2,4,6-tripheny1-2,3-dihydro-4H-pyran.Communication 1, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1321–1324, October, 1986.