Direct one-pot synthesis of zolimidine pharmaceutical drug and imidazo[1,2.a]pyridine derivatives via I2/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, α/βunsaturated ketones,β-keto esters and 2- aminopyridines. The present reaction proceeded well in MeOH under the media of I2/CuO. By using...

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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 Elsevier B.V 01.07.2015
Subjects
2-Aminopyridines
Aromatic ketones
CuO
Imidazo[1,2-a]pyridines
One-pot
Zolimidine
β-酮酸酯
一步法合成
串联
吡啶衍生物
咪唑
晶体学分析
药物
Imidazo[1,2-a]pyridines
Zolimidine
One-pot
Aromatic ketones
2-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, α/βunsaturated ketones,β-keto esters and 2- aminopyridines. The present reaction proceeded well in MeOH under the media of I2/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 bv X-ray crystallographic analysis.
Bibliography:2-AminopyridinesAromatic ketoneslmidazo[ 1,2-a]pyridines ZolimidineOne-pot
11-2710/O6
An efficient one-pot synthetic protocol was developed for the synthesis of imidazo[ 1,2-a]pyridines from easily available starting materials： Aromatic ketones, α/βunsaturated ketones,β-keto esters and 2- aminopyridines. The present reaction proceeded well in MeOH under the media of I2/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 bv X-ray crystallographic analysis.
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2014.12.016