9-氯-6,7-二甲氧基-2,3-二氢-1H-环戊二烯并[b]喹啉的合成

Synthesis of 9-chloro-6,7-dimethoxy-2,3-dihydro-1H-cyclopenta[b]quinoline

报道一种9-氯-6,7-二甲氧基-2,3-二氢-1H-环戊二烯并[b]喹啉的简便制备方法。以2-氨基-4,5-二甲氧基苯甲酸和环戊酮为原料,在三氯氧磷作用下"一锅法"合成目标化合物9-氯-6,7-二甲氧基-2,3-二氢-1H-环戊二烯并[b]喹啉。产物结构经~1H NMR和ESI-MS确证。最佳反应条件为:环戊酮用量为1.5当量,120℃反应12 h,产物收率76.4%。按照最佳反应条件对于底物进行拓展,2-氨基-4,5-二甲氧基苯甲酸和环己酮反应得到9-氯-6,7-二甲氧基-1,2,3,4-四氢吖啶,收率64.2%。

9-Chloro-6,7-dimethoxy-2,3-dihydro-1H-cyclopenta[b]quinolonewas synthesized by an efficient and practical method from 2-amino-4,5-dimethoxybenzoic acid and cyclopentanone inthe presence ofphosphorus oxychloride by one pot.The structure of the product was confirmed by^1H NMR and ESI-MS.The optimal reaction conditions were investigated.Target compound was obtained in a yield of 76.4%with 2-amino-4,5-dimethoxybenzoic acidas starting material,1.5 equvilent of cyclopentanone was used at 120℃for 12 h in phosphorus oxychloride as solvent.The synthetic method wasused for synthesis of 9-chloro-6,7-dimethoxy-1,2,3,4-tetrahydroacridine in a yield of 64.2%.