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目的研究醛糖还原酶抑制剂达瑞司他的合成方法。方法以4-甲氧基苯胺为起始原料,经N-酰化、环合、分子内傅克酰基化反应得到关键中间体6-甲氧基-2,3-二氢-4(1H)-喹啉酮,再经烃化、水解、缩合并重排得到目标化合物。结果经5步反应合成了目标化合物,总收率质量分数为42.4%,纯度达到99.9%以上,目标化合物的结构经MS、1H-NMR、13C-NMR和IR确证。结论本合成方法适合工业化生产。
Objective To study the synthesis of aldose reductase inhibitor darrestat. Methods Starting from 4-methoxyaniline, the key intermediate 6-methoxy-2,3-dihydro-4 (1H) -indole was obtained via N-acylation, cyclization and intramolecular Friedel- - quinolinone, and then by alkylation, hydrolysis, condensation and rearrangement to give the target compound. Results The target compounds were synthesized in 5 steps with the total yield of 42.4% and the purity of over 99.9%. The structures of target compounds were confirmed by MS, 1H-NMR, 13C-NMR and IR. Conclusion This synthetic method is suitable for industrial production.