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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
Author(s) -
Fan XueSen,
Zhang Ju,
Li Bin,
Zhang XinYing
Publication year - 2015
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201500266
Subject(s) - amination , catalysis , chemistry , copper , combinatorial chemistry , medicinal chemistry , organic chemistry
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.