Direct one-pot synthesis of zolimidine pharmaceutical drug and imidazo[1,2-a]pyridine derivatives via I-2/CuO-promoted tandem strategy

An efficient one-pot synthetic protocol was developed for the synthesis of imidazo[1,2-a]pyridines from easily available starting materials: Aromatic ketones, alpha,beta-unsaturated ketones, beta-keto esters and 2-aminopyridines. The present reaction proceeded well in MeOH under the media of I-2/CuO...

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Bibliographic Details
Published inChinese chemical letters Vol. 26; no. 7; pp. 881 - 884
Main Authors Cai, Qun, Liu, Mei-Cai, Mao, Bi-Ming, Xie, Xuan, Jia, Feng-Cheng, Zhu, Yan-Ping, Wu, An-Xin
Format Journal Article
LanguageEnglish
Published NEW YORK Elsevier 01.07.2015
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
2-Aminopyridines
Imidazo[1,2-a]pyridines
Zolimidine
One-pot
Aromatic ketones
IODINATION
BETA-KETO-ESTERS
INHIBITORS
EFFICIENT
AMINOPYRIDINES
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Summary:An efficient one-pot synthetic protocol was developed for the synthesis of imidazo[1,2-a]pyridines from easily available starting materials: Aromatic ketones, alpha,beta-unsaturated ketones, beta-keto esters and 2-aminopyridines. The present reaction proceeded well in MeOH under the media of I-2/CuO. By using this method, the marketed drug zolimidine could be prepared easily with 95% yield. All these target products were characterized by NMR, HRMS and IR spectra. Furthermore, the target compound 3fa was determined by X-ray crystallographic analysis. (C) 2014 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2014.12.016