クマリン誘導体の合成研究 (第7報)

アミノクマリン-3-カルボン酸誘導体の合成

抄録

2-Hydroxy-5-Acetylaminobenzylideneaniline (I) was prepared by the reduction of 5-acetylaminosalicylic acid with sodium amalgam, in the presence of aniline, and (I) was derived to 6-acetylaminocoumarin-3-carboxylic acid (II), its ethyl ester (IV), and 6-aminocoumarin-3-carboxylic acid (III) and its ethyl ester (V) (cf. Fig. 1). The products obtained by the catalytic and chemical reduction of 6-nitrocoumarin-3-carboxylic acid and its ethyl ester were confirmed to be (III) and (V). 4-Aminosalicylic acid was derived, similarly as the 6-amino derivative, to 7-acetylaminocoumarin-3-carboxylic acid (VII) and its ethyl ester (IX), and 7-aminocoumarin-3-carboxylic acid (VIII) and its ethyl ester (X) (cf. Fig. 2). It was observed that the reduction of 7-nitrocoumarin-3-carboxylic acid and its ethyl ester also yielded the 7-amino derivatives. Both the 7-amino and 7-acetylamino derivatives thereby obtained possessed a strong fluorescence.