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| Direct one-pot synthesis of zolimidine pharmaceutical drug and imidazo[1,2-a]pyridine derivatives via I2/CuO-promoted tandem strategy |
| Qun Cai, Mei-Cai Liu, Bi-Ming Mao, Xuan Xie, Feng-Cheng Jia, Yan-Ping Zhu, An-Xin Wu |
| Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, China |
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| Guide An effi cient one-pot synthetic protocol was developed for the synthesis of imidazo[1,2-a] pyridines from easily available starting materials. All the desired products were obtained in moderate to good yields. Moreover, this protocol can also be further applied towards the synthesis of the marketed antiulcer drug zolimidine with 95% yield |
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Abstract 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,β-unsaturated ketones, β-keto esters and 2- aminopyridines. The present reaction proceeded well in MeOH under the media of I2/CuO. By using this method, themarketed 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.
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Received: 04 November 2014
Published: 02 January 2015
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| Fund: We would like to thank the National Natural Science Foundation of China (Nos. 21032001 and 21272085) for their generous financial support. We acknowlege the excellent doctorial dissertation cultivation grant from Central China Normal University Wuhan, China (No. 2013YBYB63). We also thank Dr. Chuanqi Zhou, Hebei University, for analytical support. |
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Corresponding Authors:
An-Xin Wu
E-mail: chwuax@mail.ccnu.edu.cn
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| [1] |
A.R. Katritzky, Y.J. Xu, H. Tu, Regiospecific synthesis of 3-substituted imidazo[1,2- a]pyridines, imidazo[1,2-a]pyrimidines, and imidazo[1,2-c]pyrimidine, J. Org. Chem. 68 (2003) 4935-4937 (and references therein).
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