Abstract
Reactions of acetoacetamide (I) and β-aminocrotonamide (II) with 1, 3-dioxo and related compounds were investigated. Namely, the reaction of I with 2, 4-pentanedione (III), 4-methoxy-3-pentene-2-one (VIII), 2-formylcyclohexanone (IV), 4-hydroxy-3-butene-2-one (Va), ethyl 2-ethoxymethyleneacetoacetate (Vb), and 3-ethoxymethylene-2, 4-pentanedione (Vc) afforded 3-acetyl-4, 6-dimethyl-2 (1H)-pyridone (IX), 3-acetyl-5, 6, 7, 8-tetrahydro-2-quinolone (X), 3-acetyl-6-methyl-2 (1H)-pyridone (XIa), ethyl 5-acetyl-6-methyl-2 (1H)-pyridone-3-carboxylate (XIb), and 3, 5-diacetyl-6-methyl-2 (1H)-pyridone (XIc), respectively. On the other hand, the reaction of II with III, 4-amino-3-penten-2-one (VI), 4, 4-dimethoxy-2-butanone (VII), and IV resulted in the formation of 2, 4, 6-trimethyl-3-pyridinecarboxamide (XII), 2, 6-dimethyl-3-pyridinecarboxamide (XV), and 2-methyl-5, 6, 7, 8-tetrahydro-3-quinolinecarboxamide (XIV), respectively. In the case of the reaction of II with Vb, ethyl 5-carbamoyl-2, 6-dimethyl-3-pyridinecarboxylate (XVIIa), ethyl 2-[(2-carbamoyl-1-methylvinylamino) methylene] acetoacetate (XVIIIa) were obtained. Similarly, II reacted with Vc to give 5-acetyl-2, 6-dimethyl-3-pyridinecarboxamide (XVIIb) and 3-[(2-carbamoyl-1-methylvinylamino) methylene]-2, 4-pentanedione (XVIIIb).
