アセトブチロラクトンより誘導される異項環化合物の合成研究 (第7報)

ニトロアニリンとアセトブチロラクトンの縮合生成物について

抄録

When 2-[1-(3-nitrophenylimino)ethyl]-γ-butyrolactone is heated with phosphoryl chloride, a 7-nitroquinoline-type compound, 4-methyl-7-nitro-2, 3-dihydrofuro[2, 3-c]-quinoline (II), is formed, with a small amount of 3-(2-chloroethyl)-4-chloro-7-nitroquinaldine (III) as a by-product. When a mixture of 2-acetyl-γ-butyrolactone and phosphoryl chloride is heated, 7-nitro compound (II) and a 5-nitro compound, 3-(2-chloroethyl)-4-chloro-5-nitroquinadine (IV), are formed in 5:4 ration. Heating of (II) further with phosphoryl chloride results in its conversion to (III), while heating of (III) with acetic acid regenerates (II). Therefore, it is found that these compounds are cyclization products of the same type. (IV) and 4-methyl-9-nitro-2, 3-dihydrofuro[3, 2-c]quinoline (V) also undergo the same reaction. (III) was derived to 2-methyl-3-(2-chloroethyl)-4-chloro-7-quinolinol (VII) and the positions of nitro group in (II) to (V) were confirmed.