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氢化物诱导的阴离子环化反应:一种通过无过渡金属过程高效合成6-H-菲啶的方法。

Hydride-induced anionic cyclization: an efficient method for the synthesis of 6-H-phenanthridines via a transition-metal-free process.

作者信息

Chen Wei-Lin, Chen Chun-Yuan, Chen Yan-Fu, Hsieh Jen-Chieh

机构信息

Department of Chemistry, Tamkang University, New Taipei City, 25137, Taiwan.

出版信息

Org Lett. 2015 Mar 20;17(6):1613-6. doi: 10.1021/acs.orglett.5b00544. Epub 2015 Mar 12.

Abstract

A novel procedure for hydride-induced anionic cyclization has been developed. It includes the reduction of a biaryl bromo-nitrile with a nucleophilic aromatic substitution (S(N)Ar). A range of polysubstituted 6-H-phenanthridines were so obtained in moderate to good yield with good substrate tolerance. This method involves a concise transition-metal-free process and was applied to synthesize natural alkaloids.

摘要

已开发出一种用于氢化物诱导阴离子环化的新方法。该方法包括通过亲核芳香取代反应(S(N)Ar)还原联芳基溴腈。由此以中等至良好的产率获得了一系列多取代的6-H-菲啶,且底物耐受性良好。该方法涉及一个简洁的无过渡金属过程,并被应用于天然生物碱的合成。

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