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Ortho-substituent effect promoted rapid cleavage of amide C–N bond under mild conditions

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Abstract

This article reports the ortho-substituent effect on the cleavage of the amide C–N bond. In the structure of N α-Phth-N-pyridinyl-amide, when the hydrogen atom in the 3-position of pyridine ring was replaced by alkoxy group, the amide C–N cleavage can take place in the 2-position of the pyridine ring. This transformation can proceed rapidly in methylamine ethanol solution under mild conditions to afford 2-amino-3-alkoxy pyridines.

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Acknowledgments

This work is supported by the National Basic Research Program of China (No. 2011CB933503) and Technology Supporting Program of Jiangsu province (BE2009639, BE2012657). H. Hu is grateful to China Postdoctoral Science Foundation funded project (No. 2012M511645) and NSFC (No. 21202058) for their financial support.

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Authors and Affiliations

  1. School of Biological Science & Medical Engineering, Southeast University, Nanjing, 210096, China

    Peng Wang, Huayou Hu & Lushen Li

  2. School of Chemistry & Chemical Engineering, Southeast University, Nanjing, 210096, China

    Jin Cai, Chunlong Sun & Min Ji

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  1. Peng Wang
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  2. Jin Cai
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  3. Huayou Hu
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  4. Lushen Li
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  5. Chunlong Sun
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  6. Min Ji
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Correspondence to Min Ji.

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Wang, P., Cai, J., Hu, H. et al. Ortho-substituent effect promoted rapid cleavage of amide C–N bond under mild conditions. Res Chem Intermed 40, 2935–2943 (2014). https://doi.org/10.1007/s11164-013-1140-1

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  • DOI: https://doi.org/10.1007/s11164-013-1140-1

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