吡咯喹啉醌关键中间体的合成工艺研究  

Synthesis of Key Intermediate of Pyrroloquinoline Quinone

作　　者：毛联岗 MAO Lian-gang(Lianyungang Jari Pharmaceutical Co.,Ltd.,Lianyungang 222000,China)

机构地区：[1]连云港杰瑞药业有限公司,江苏连云港222000

出　　处：《精细化工中间体》2022年第5期35-39,共5页Fine Chemical Intermediates

摘　　要：以1-甲氧基-5-甲基-2,4-二硝基苯(2)为原料,经缩合、还原和环合制得6-氨基-5-甲氧基-1H-吲哚-2-甲酸乙酯(4),优化条件下收率70%;4与乙醛酸酯和丙酮酸酯发生三组分一锅反应得到吡咯喹啉醌关键中间体5-甲氧基-1H-吡咯[2,3-f]喹啉-2,7,9-三甲酸2-乙酯7,9二烷基酯(1),优化条件下收率90%。对影响收率的催化剂结构、反应温度、溶剂、乙醛酸酯和丙酮酸酯结构等因素进行了考察。通过IR、^(1)H NMR、^(13)C NMR和ESI-MS确证了1及中间体的结构。该制备工艺原料价廉、环保,收率高,具有工业化应用前景。Ethyl 6-amino-5-methoxy-1H-indole-2-carboxylate(4)was obtained from 1-methoxy-5-methyl-2,4-dinitrobenzene(2)through condensation,reduction and cyclization with a yield of 70%.Then 2-ethyl,7,9-dialkyl 5-methoxy-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid ester(1)was synthesized from 4 and glyoxylic ester,pyruvate through a simple one-pot reaction with a yield of 90%.The affecting factors including the structures of the catalysts,the reaction temperature,the solvent,and the structures of glyoxylic ester and pyruvate were investigated.The structures of the compound 1 and intermediate were characterized by IR,^(1)H NMR,^(13)C NMR and ESI-MS.The synthetic process had the advantages including low in raw material cost,environment-friendly,high yield and suitable for industrial production.

关 键 词：吡咯喹啉醌 5-甲氧基-1H-吡咯[2 3-f]喹啉-2 7 9-三甲酸2-乙酯7 9二烷基酯 一锅反应 

分 类 号：O626[理学—有机化学]