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芳基乙炔作为双碳合成子:通过C≡C键裂解合成八元环。

Arylacetylenes as two-carbon synthons: synthesis of eight-membered rings via C[triple bond, length as m-dash]C bond cleavage.

作者信息

Zhao Peng, Yu Xiao-Xiao, Zhou You, Huang Chun, Wu Yan-Dong, Zhu Yan-Ping, Wu An-Xin

机构信息

Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. China.

出版信息

Chem Commun (Camb). 2020 Oct 25;56(83):12554-12557. doi: 10.1039/d0cc05363e. Epub 2020 Sep 17.

DOI:10.1039/d0cc05363e
PMID:32940307
Abstract

The first synthesis of eight-membered N-containing heterocycles by oxidative bicyclization/ring extension of arylacetylenes and aryl amines has been achieved. This protocol uses arylacetylene as an unusual two-carbon synthon by incorporating the two parts of the cracked C[triple bond, length as m-dash]C bond into the final product, which provides a new method for using arylacetylenes as two-carbon synthons and further enriches C[triple bond, length as m-dash]C bond cleavage methodology. Moreover, this multi-component reaction can provide diverse fused elegant eight-membered N-heterocycles under mild conditions with wide substrate scopes.

摘要

通过芳基乙炔和芳基胺的氧化双环化/扩环反应首次实现了八元含氮杂环的合成。该方法通过将断裂的C≡C键的两部分并入最终产物中,将芳基乙炔用作一种特殊的双碳合成子,这为将芳基乙炔用作双碳合成子提供了一种新方法,并进一步丰富了C≡C键断裂方法。此外,这种多组分反应可以在温和条件下、底物范围广泛的情况下提供多种稠合的优雅八元氮杂环。

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