Isoindoline 유도체의 합성연구 III 이염기산무수물 또는 Imjde에 대한 유기산의 Gabriel 축합반응에 관한 연구

Studies on Isoindoline Derivatives. III. Studies on the Anhydrides and Imides of Dibasic Acids for the Organic Acids in the Gabriel Condensation

Fifteen derivatives of phthalide were synthesized from m-hemipinic, hydrastic, and 4,5-benzophthalic anhydride with acetic, phenylacetic, p-methoxyphenylacetic, p-nitrophenylacetic, P-naphthylacetic and succinic acid by the Gabriel condensation. In the same way, 13 derivatives of phthalimidine and 4 derivatives of alpha,beta-benzisothiazoline-1, 1-dioxide were synthesized from diphenylmaleimide, phthalimide, saccharine and 4,5-benzo-phthalimide with previous 6 acids. 3-Substituted derivatives of m-hemipinic anhydride, hydrastic anhydride and 4,5-benzophthalic anhydride were treated with formamide and seven 3-substituted imidines could be synthesized. In case of 4,5-benzophthalide, two isomers,4,5-benzophthalidene-3-acetic acid and 4,5-benzophthalidene-1-acetic acid, can be obtained theoretically, but only one product we got, and the chemical structure of it was identified by the following way, It was hydrolyzed and then decarboxylated, and this decomposed product was identical with 1-acetyl-2-naphthoic acid which was synthesized from p-naphthylamine. This indicates that by the Gabriel condensation 4,5-benzophthalide only produces 4,5-benzophthlidene-3-acetic acid, that is alpha-carbonyl substitute.