期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 15, 期 46, 页码 12608-12617出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200902411
关键词
alkynes; cyanides; multicomponent reactions; nitrogen heterocycles; zirconium
资金
- National Natural Science Foundation of China
- Cheung Kong Scholars Program
- Dow Corning Corporation
- Qiu Shi Science & Technologies Foundation
- BASF
A zirconocene-mediated one-pot multicomponent synthesis process leading to the synthesis of pyrrolo[3,2-c]pyridine (5-azaindoles) and pyrrole derivatives has been developed starting from a silicon-tethered diyne and three or two different or identical organonitriles. Pyrrolo[3,2-c]pyridine and pyrrole derivatives with diverse structures and substitution patterns have been highly selectively prepared by this protocol. A wide variety of organonitriles and silicon-tethered diynes, either aliphatic or aromatic with both electron-withdrawing and -donating groups, have been used to afford 5-azaindoles and/or pyrroles in good-to-excellent isolated yields. A key intermediate formed in the Cp2Zr11-mediated reaction of one (PhC C)(2)SiMe2, two molecules of iPrCN and one p-tolylCN was characterised by Xray single-crystal structural analysis, which has allowed us to gain a good understanding of the reaction process.
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