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One-pot three-component Mannich reaction catalyzed by 2-hydroxylpyridine

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Abstract

An effcient synthetic protocol for the β-amino carbonyl compounds was developed via one-pot three-component Mannich reaction of aromatic aldehydes, aromatic amines and cyclohexanone catalyzed by 2-hydroxylpyridine under mild reaction conditions. β-Amino carbonyl compounds were obtained in moderate to good yields and reasonable diastereoselectivities. The effects of different solvents, catalyst amounts and the scope of different substrates on the Mannich reactions were investigated. The plausible reaction mechanism was also discussed.

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References

  1. Azend M., Westermann B., Risch N., Angew. Chem. Int. Ed., 1998, 37, 1044

    Article  Google Scholar 

  2. Córdova A., Acc. Chem. Res., 2004, 37(2), 102

    Article  Google Scholar 

  3. Kobayashi S., Ishitani H., Chem. Rev., 1999, 99(5), 1069

    Article  CAS  Google Scholar 

  4. Josephsohn N. S., Carswell E. L., Snapper M. L., Hoveyda A. H., Org. Lett., 2005, 7(13), 2711

    Article  CAS  Google Scholar 

  5. Trost B. M., Terrell L. R., J. Am. Chem. Soc., 2003, 125(2), 338

    Article  CAS  Google Scholar 

  6. Wu M., Jing H. W., Chang T., Catal. Commun., 2007, 8, 2217

    Article  CAS  Google Scholar 

  7. Li Z., Ma X., Liu J., Feng X., Tian G., Zhu A., J. Mol. Catal. A: Chem., 2007, 272, 132

    Article  CAS  Google Scholar 

  8. Li H., Zeng H. Y., Shao H. W., Tetrahedron Lett., 2009, 50, 6858

    Article  CAS  Google Scholar 

  9. Mukhopadhyay C., Datta A., Butcher R. J., Tetrahedron Lett., 2009, 50, 4246

    Article  CAS  Google Scholar 

  10. Guo Q., Liu H., Guo C., Luo S., Gu Y., Gong L., J. Am. Chem. Soc., 2007, 129(13), 3790

    Article  CAS  Google Scholar 

  11. Azizi N., Torkiyan L., Saidi M. R., Org. Lett., 2006, 8(10), 2079

    Article  CAS  Google Scholar 

  12. Dziedzic P., Ibrahem I., Córdova A., Tetrahedron Lett., 2008, 49, 803

    Article  CAS  Google Scholar 

  13. Teo Y., Lau J., Wu M., Tetrahedron: Asymmetry, 2008, 19, 186

    Article  CAS  Google Scholar 

  14. Wang Y., Fu A. P., Li H. L., Tian F. H., Yuan S. P., Si H. Z., Duan Y. B., Wang Z. H., Chem. Res. Chinese Universities, 2011, 27(4), 673

    CAS  Google Scholar 

  15. Wang L., Han J., Sheng J., Tian H., Fan Z., Catal. Commun., 2005, 6, 201

    Article  CAS  Google Scholar 

  16. Fang D., Fei Z., Liu Z., Catal. Commun., 2009, 10, 1267

    Article  Google Scholar 

  17. Sahoo S., Joseph T., Halligudi S. B., J. Mol. Cata. A: Chem., 2006, 244, 179

    Article  CAS  Google Scholar 

  18. Liu B. Y., Zhao D. S., Xu D. Q., Xu Z. Y., Chem. Res. Chinese Universities, 2007, 23(2), 163

    Article  Google Scholar 

  19. Zhang H., Mifsud M., Tanaka F., Barbas C. F., J. Am. Chem. Soc., 2006, 128(30), 9630

    Article  CAS  Google Scholar 

  20. Kang Y. K., Kim D. Y., J. Org. Chem., 2009, 74(15), 5734

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. College of Sciences, China Pharmaceutical University, Nanjing, 210009, P. R. China

    Li-li Jin & Yun-tao Lei

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  1. Li-li Jin
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  2. Yun-tao Lei
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Correspondence to Yun-tao Lei.

Additional information

Supported by the Fundamental Research Funds for the Central Universities, China(No.JKQ2011003).

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Jin, Ll., Lei, Yt. One-pot three-component Mannich reaction catalyzed by 2-hydroxylpyridine. Chem. Res. Chin. Univ. 29, 710–713 (2013). https://doi.org/10.1007/s40242-013-2362-x

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  • DOI: https://doi.org/10.1007/s40242-013-2362-x

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