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

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


Abstract

Fifteen derivatives of phthalide were synthesized from m-hemipinic, hydrastic and 4,5-benzophthalic anhydride with acetic, phenylacetic, p-methoxyphenylacetic, p-nitrophenylacetic, ${\alpha}$-nephthylacetic 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-benzophtha lide, 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 .betha.-naphthylamine. This indicates that by the Gabriel condensatioin 4,5-benzophthalide only produces 4,5-benzophthlidene-3-acetic acid, that is ${\alpha}$-carbonyl substitute.

Keywords