Directed Solid-Phase Synthesis of Trisubstituted Imidazo[4,5-c]pyridines and Imidazo[4,5-b]pyridines
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- 作者：Barbora Lemrov谩 ; Petra Smyslov谩 ; Igor Popa ; Tom谩拧 O啪dian ; Pawel Zajdel ; Miroslav Soural
- 刊名：ACS Combinatorial Science
- 出版年：2014
- 出版时间：October 13, 2014
- 年：2014
- 卷：16
- 期：10
- 页码：558-565
- 全文大小：443K
- ISSN：2156-8944
文摘
An efficient method is described for the solid-supported synthesis of imidazo[4,5-b]pyridines and imidazo[4,5-c]pyridines from 2,4-dichloro-3-nitropyridine. The key pyridine building block was reacted with polymer-supported amines, followed by replacement of the second chlorine with amines, nitro group reduction, and imidazole ring closure with aldehydes. Depending on the combination of polymer-supported and solution-phase reagents, the strategy allowed for the simple preparation of the target trisubstituted derivatives with variable positioning of the pyridine nitrogen atom. Additionally, after a slight modification of the method, the preparation of strictly isomeric imidazopyridines was possible.