title: One-pot Sequential Reactions Featuring a Copper-catalyzed Amination Leading to Pyrido[2',1':2,3]imidazo[4,5-c]quinolines and Dihydropyrido[2',1':2,3]imidazo[4,5-c]quinolines.
abstract: Tetracyclic skeletons combining an imidazo[1,2-a]pyridine moiety with a quinoline framework such as pyrido[2',1':2,3]imidazo[4,5-b]quinoline are stimulating increasing interests since they are close isosteres of a series of powerful antiproliferative compounds. In this paper, we report a novel methodology for the synthesis of pyrido[2',1':2,3]imidazo[4,5-c]quinolines through one-pot sequential reactions of commercially available or readily obtainable 2-aminopyridines, 2-bromophenacyl bromides, aqueous ammonia, and aldehydes. Moreover, dihydropyrido[2',1':2,3]imidazo[4,5-c]quinolines could also be obtained in a similar manner by using various ketones as the substrates in place of aldehydes. Notably, the whole procedure combines condensation/amination/cyclization reactions in one pot to give complex compounds in a simple and practical manner. Compared with literature methods, the synthetic strategy reported herein has the advantages of readily available starting materials, structural diversity of products, good functional group tolerance, and obviation of step-by-step operations.
authors: School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Key Laboratory for Environmental Pollution Control, Henan Normal University, 46 Jianshe Road, Xinxiang, Henan, 453007, P. R. China. xuesen.fan@htu.cn.
authors: Xue-Sen
authors: XS
authors: Fan
authors: School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Key Laboratory for Environmental Pollution Control, Henan Normal University, 46 Jianshe Road, Xinxiang, Henan, 453007, P. R. China.
authors: Ju
authors: J
authors: Zhang
authors: School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Key Laboratory for Environmental Pollution Control, Henan Normal University, 46 Jianshe Road, Xinxiang, Henan, 453007, P. R. China.
authors: Bin
authors: B
authors: Li
authors: School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Key Laboratory for Environmental Pollution Control, Henan Normal University, 46 Jianshe Road, Xinxiang, Henan, 453007, P. R. China. xinyingzhang@htu.cn.
authors: Xin-Ying
authors: XY
authors: Zhang
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000586:Amination; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D011725:Pyridines; D011804:Quinolines; D003300:Copper; C023666:pyridine
keywords: 5,6-dihydropyrido[2′,1′:2,3]imidazo[4,5-c]quinolines; amination; copper catalysis; one-pot sequential reaction; pyrido[2′,1′:2,3]imidazo[4,5-c]quinolines