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Intramolecular Cycloaddition of Azomethine Ylides Activated by Aromatic Rings: Scope and Limitations

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Chemistry of Heterocyclic Compounds Aims and scope

Simple aromatic substituents in the substrate molecule, including pyrimidine, pyridine, and benzene rings, directly facilitated the intramolecular cycloaddition of azomethine ylide to alkene. All of these aromatic substituents aided the formation of azomethine ylides, which then underwent highly diastereospecific sequential cycloaddition. It was shown that both the presence of an electron-deficient aromatic ring and a substituent at ortho position of the aromatic ring relative to the aminomethyl group enhanced the reactivity of azomethine ylides towards cycloaddition.

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This work was supported by a grant from the Sci-Tech Development Project of Jilin Province in China (No. 20160520039JH) and a grant from the Norman Bethune Program of Jilin University (No. 2015330). Additional support was provided by Changchun Discovery Sciences, Ltd.

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Authors and Affiliations

  1. The Center for Combinatorial Chemistry and Drug Discovery of Jilin University, The School of Pharmaceutical Sciences, Jilin University, 1266 Fujin Road, Changchun, Jilin, 130021, P. R. China

    Hongxiang Xie, Bowen Gong, Xinran Zhong, Hongming Cui & Jinbao Xiang

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  1. Hongxiang Xie
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  2. Bowen Gong
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  3. Xinran Zhong
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  4. Hongming Cui
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  5. Jinbao Xiang
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Correspondence to Jinbao Xiang.

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The Supplementary information file containing NMR spectra of all new compounds is available at http://link.springer.com/journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(7), 484–492

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Xie, H., Gong, B., Zhong, X. et al. Intramolecular Cycloaddition of Azomethine Ylides Activated by Aromatic Rings: Scope and Limitations. Chem Heterocycl Comp 52, 484–492 (2016). https://doi.org/10.1007/s10593-016-1912-9

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  • DOI: https://doi.org/10.1007/s10593-016-1912-9

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