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本文通过β-二酮与丙烯腈反应合成了三个二酮的一氰乙基化合物:4-乙酰基-5-氧代己腈(Ⅰ),4-乙酰基-5-氧代庚腈(Ⅱ)及4-苯甲酰基-5-氧代已腈(Ⅲ).(Ⅰ)—(Ⅲ)环合得到了三个未饱和内酰胺:5-乙酰基-6-甲基3,4-二氢化-2(1H)吡啶酮(Ⅳ),5-丙酰基-6-甲基3,4-二氢化-2(1H)吡啶酮(Ⅴ),5-苯甲酰基-6-甲基3,4-二氢化-2(1H)吡啶酮(Ⅵ)。(Ⅰ)—(Ⅲ)和(Ⅳ)—(Ⅵ)水解得到了相应的酮酸:4-乙酰基-5-氧代已酸(Ⅶ),4-乙酰基-5-氧代庚酸(Ⅷ),和4-苯甲酰基-5-氧代已酸(Ⅸ)。(Ⅳ)—(Ⅵ)与2,4-二硝基苯肼反应得到了相应的酮腙(Ⅹ)—(Ⅻ)。以上化合物中(Ⅱ)、(Ⅲ)、(Ⅴ)、(Ⅵ)、(Ⅷ)、(Ⅸ)、(Ⅹ)、(Ⅺ)、(Ⅻ)是未知物。
In this paper, three diketones were synthesized by the reaction of β-diketone with acrylonitrile: 4-acetyl-5-oxohexanenitrile (Ⅰ), 4-acetyl- (Ⅱ) and 4-benzoyl-5-oxononitrile (Ⅲ). The cyclization of (Ⅰ) - (Ⅲ) gave three unsaturated lactams: 5-acetyl- (IV), 5-propionyl-6-methyl 3,4-dihydro-2 (1H) pyridone (V), 5- benzoyl-6-methyl 3 , 4-dihydro-2 (1H) pyridone (VI). Hydrolysis of (I) - (III) and (IV) - (VI) gives the corresponding keto acids: 4-acetyl-5-oxohexanoic acid VIII), and 4-benzoyl-5-oxohexanoic acid (IX). Reaction of (Ⅳ) - (Ⅵ) with 2,4-dinitrophenylhydrazine afforded the corresponding ketohydrazone (X) - (XII). Among the above compounds, (II), (III), (V), (VI), (VIII), (IX), (X), (XI) and (XII) are unknown.