Novel Annelations of Xanthines by the Reaction of 8-Aminoxanthines with Dimethyl Acetylene-dicarboxylate

概要

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Annelations of xanthines by the reaction of dimethyl acetylenedicarboxylate (DMAD) with 7-alkyl-8-amino-1,3-dimethylxanthines (3) have been investigated. Treatment of 3 with DMAD in refluxing methanol gave 5-alkyl-1,3-dimethyl-9-methoxycarbonyl-1,2,3,4-tetrahydro-5H, 7H-pyrimido[1,2-e]purine-2,4,7-triones (4) and 7-alkyl-1,2,3,6-tetrahydro-1,3-dimethyl-8-(1,2,4,5,6,7-hexamethoxycarbonyl-3-azatricyclo[2.2.1.0^<2,6>]heptyl)purine-2,6-diones (10). However, when the reaction was run in N, N-dimethylformamide, 5-alkyl-1,3-dimethyl-1,2,3,4-tetrahydro-7,8,11-tris(methoxycarbonyl)-5H, 9H[1,3]-diazocino[1,2-e]purine-2,4,9-triones (11), 5-alkyl-1,3-dimethyl-7,8-bis(methoxy-carbonyl)-1,2,3,4,9,10-hexahydro-10-(methoxycarbonyl)methylene-5H[1,3]-diazepino[1,2-e]purine-2,4,9-triones (12), and 5-alkyl-1,3-dimethyl-1,2,3,4,9,10-hexahydro-7,8,9,10-tetrakis(methoxycarbonyl)-5H[1,3]-diazepino[1,2-e]purine-2,4-diones (13) were formed.
社団法人日本薬学会の論文
1991-02-25