通过 Pd 催化的 Suzuki-Miyaura 偶联和 Cu 催化的酰胺化反应[已更正]，从乙基 4-溴-6-甲氧基-1,5-萘啶-3-羧酸酯三步合成 Ethyl Canthinone-1-羧酸酯。
Three-step synthesis of Ethyl Canthinone-1-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 [corrected].
机构信息
Department of Chemistry, University of Cyprus, P.O. Box 20537, 1678 Nicosia, Cyprus.
出版信息
J Org Chem. 2011 Jun 17;76(12):5113-22. doi: 10.1021/jo200824b. Epub 2011 May 25.
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.
乙基咔啉-6-酮-1-羧酸酯（1b）和九个类似物 1c-k 由易于制备的乙基 4-溴-6-甲氧基-1,5-萘啶-3-羧酸酯（2b）通过三步非经典方法制备，该方法重点使用 Pd 催化的 Suzuki-Miyaura 偶联构建中心吡咯（环 B），然后进行 Cu 催化的 C-N 偶联。此外，在 DCM/MeOH（9:1）中用 NaOH 处理乙基咔啉酮-1-羧酸酯 1b 可高产率得到咔啉-6-酮-1-羧酸（6）。所有化合物均经过充分表征。
Zotero 插件