ケテンおよびその誘導体の研究(第37報) : Ketone Anilおよび関連化合物とジケテンとの反応

抄録

Reaction of ketone anil (I) and diketene in acetic acid, in the presence of p-tolueneSulionic acid, results in the formation of 4-pyridone derivatives. Reaction with acetophenone anil (Ia), propiophenone anil (Ib), deoxybenzoin anil (Ic), cyclohexanone anil (Id), and cyclopentanone anil (Ie) respectively afforded 1, 2-diphenyl-6-methyl-(IIa), 3, 6-dimethyl-1, 2-diphenyl-(IIb), 6-methyl-1, 2, 3-triphenyl-4-pyridone (IIc), 2-methyl-1-phenyl-5, 6, 7, 8-tetrahydro-4-quinolone (IId), and 2-methyl-1-phenyl-4, 5, 6, 7-tetrahydro-1H-cyclopenta [b] pyrid-4-one (IIe). It was also found that the product from the reaction of β-diketone anil, i. e., N-phenylsec-enamine (V), and diketene was a 4-pyridone derivative. For example, reaction of V with 3-anilino-1-phenyl-2-buten-1-one (Vb), 3-anilino-5, 5-dimethyl-(Vd) and 3-anilino-2-cyclohexenone (Ve) respectively afforded 3-benzoyl-2, 6-dimethy1-1-phenyl-4-pyridone (VIb), 2, 7, 7-trimethyl-(VId) and 2-methyl-1-phenyl-5, 6, 7, 8-tetrahydroquinoline-4, 5-dione (IVe). However, 4-anilino-3-penten-2-one (Va) and ethyl β-anilinocrotonate (Vc) do not react under these conditions but reacted in acetone, in the presence of triethylamine, to respectively form 3-acetyl-(VIa) and 3-ethoxycarbonyl-2, 6-dimethyl-1-pentyl-4-pyridone (VIc).