Three-Step Synthesis of Ethyl Canthinone-3-carboxylates from Ethyl 4-Bromo-6-methoxy-1,5-naphthyridine-3-carboxylate via a Pd-Catalyzed Suzuki-Miyaura Coupling and a Cu-Catalyzed Amidation Reaction
Three-Step Synthesis of Ethyl Canthinone-3-carboxylates from Ethyl 4-Bromo-6-methoxy-1,5-naphthyridine-3-carboxylate via a Pd-Catalyzed Suzuki-Miyaura Coupling and a Cu-Catalyzed Amidation Reaction
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DOI：
10.1021/jo200824b
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发表时间：
2011-06-17
影响因子：
3.6
通讯作者：
Koutentis, Panayiotis A.
中科院分区：
文献类型：
--
作者：
Ioannidou, Heraklidia A.;Martin, Aaron;Koutentis, Panayiotis A.
以易得的乙基4-bromo-6-methoxy-1，5-naphthyridine-3-carboxylate(2b)为原料，通过三步非经典方法合成了角豆素-6-酮-1-羧酸乙酯(1b)和9个类似物1c-k。此外，在DCM/MeOH(9：1)中用氢氧化钠处理角豆素-1-羧酸乙酯1b，得到高产率的角豆素-6-酮-1-羧酸(6)。所有化合物都经过了充分的表征。
Ethyl canthin-6-one-1-carboxylate (1b) and nine analogues 1c-k were prepared from readily prepared ethyl 4-bromo-6-methoxy-1,5-naphthyridine-3-carboxylate (2b) via a three-step non-classical approach that focused on construction of the central pyrrole (ring B) using Pd-catalyzed Suzuki-Miyaura coupling followed by Cu-catalyzed C-N coupling. Furthermore, treatment of the ethyl canthinone-1-carboxylate 1b with NaOH in DCM/MeOH (9:1) gave the canthin-6-one-1-carboxylic acid (6) in high yield. All compounds are fully characterized.