Rearrangements of 5-acetyl-3-benzoylamino-6-(2-dimethylamino-1-ethenyl)-2H-pyran-2-one and 3-benzoylamino-6-(2-dimethylamino-1-ethenyl)-5-ethoxycarbonyl-2H-pyran-2-one into 1-amino-pyridine,pyrano[2,3-b]pyridine and isoxazole derivatives

Article abstract of DOI:10.1002/jhet.5570330449

Rearrangements of 5-acetyl-3-benzoylamino-6-(2-dimethylamino-1-ethenyl)-2H-pyran-2-one (1) and 3-benzoylamino-6-(2-dimethylamino-1-ethenyl)-5-ethoxycarbonyl-2H-pyran-2-one (7) in the presence of N-nucleophiles, such as ammonia, hydrazine, and hydroxylamine, into 1-aminopyridine, pyrano[2,3-b]-pyridine, and isoxazole derivatives 5, 11, and 15 is described. In the reaction of compounds 1 and 7 with C-nucleophiles, such as 5,5-dimethyl-1,3-cyclohexanedione and barbituric acid, only substitution of the dimethylamino group is taking place to give the compounds 17, 18, and 20.