3位に含窒素環状イミド置換基を有する2-Pyrazolin-5-one類の合成
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概要
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1-Aryl-2-pyrazolin-5-ones (1-arylpyrazolones) and 3-anilino-1-(2,4,6-trichlorophenyl) pyrazolones having nitrogen-containing five or six membered cyclic imido substituent at each 3-position of pyrazolone and aniline moiety were synthesized by the reaction of 3-phenoxycarbonylaminopyrazolones (5) and 3-(3-phenoxycarbonylamino) anilinopyrazolones (6) with amino acid esters. Treatment of 5 and 6 with ethyl glycinates gave 3-(2,4-dioxoimidazolidin-3-yl) pyrazolones and anilinopyrazolones (3 and 4). When 5 and 6 were treated with ethyl β-alaninates, the products were not perhydropyrimidinediones but substituted ureas (7 and 8). Hydrolysis of the product (7a) derived from 5 and ethyl N-benzyl-β-alaninate gave the corresponding acid (7d). The cyclization of 7d with dicyclohexylcarbodiimide (DCC) furnished 3-(2,4-dioxoperhydropyrimidin-3-yl) pyrazolone (16). On the other hand, a condensation product (8) obtained by the reaction of 6 with ethyl N-benzyl-β-alaninate was easily cyclized with sodium ethoxide in ethanol to give imido substituted anilinopyrazolone (14).
- 公益社団法人日本薬学会の論文
- 1983-09-25