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Cerium(IV) ammonium nitrate catalyzed green synthesis of 2-substituted 2,3-dihydro- quinazolin-4(1H)-ones using a grinding technique

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Chemistry of Heterocyclic Compounds Aims and scope

An efficient and facile method for the synthesis of 2-substituted 2,3-dihydro-quinazolin-4(1H)-ones from anthranilamide with aldehydes or ketones in the presence of cerium(IV) ammonium nitrate in water by a grinding technique has been developed. The structures of the new products were proved by IR, 1H NMR, MS, and elemental analysis. A plausible mechanism for the formation of these products is proposed.

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References

  1. R. J. Alaimo and H. E. Russell, J. Med. Chem., 15, 335 (1972).

    Article  CAS  Google Scholar 

  2. H. A. Parish, R. D. Gilliom, W. P. Purcell, R. K. Browne, R. F. Spirk, and H. D. White, J. Med. Chem., 25, 98 (1982).

    Article  CAS  Google Scholar 

  3. M.-J. Hour, L.-J. Huang, S.-C. Kuo, Y. Xia, K. Bastow, Y. Nakanishi, E. Hamel, and K.-H. Lee, J. Med. Chem., 43, 4479 (2000).

    Article  CAS  Google Scholar 

  4. J. B. Jiang, D. P. Hesson, B. A. Dusak, D. L. Dexter, G. J. Kang, and E. Hamel, J. Med. Chem., 33, 1721 (1990).

    Article  CAS  Google Scholar 

  5. K. Hattori, Y. Kido, H. Yamamoto, J. Ishida, K. Kamijo, K. Murano, M. Ohkubo, T. Kinoshita, A. Iwashita, K. Mihara, S. Yamazaki, N. Matsuoka, Y. Teramura, and H. Miyake, J. Med. Chem., 47, 4151 (2004).

    Article  CAS  Google Scholar 

  6. H. Böhme and H. Böing, Arch. Pharm., 293, 1011 (1960).

    Article  Google Scholar 

  7. G. P. Cai, X. L. Xu, Z. F. Li, W. P. Weber, and P. Lu, J. Heterocycl. Chem., 39, 1271 (2002).

    Article  CAS  Google Scholar 

  8. D. Q. Shi, L. C. Rong, J. X. Wang, Q. Y. Zhuang, X. S. Wang, and H. W. Hu, Tetrahedron Lett., 44, 3199 (2003).

    Article  CAS  Google Scholar 

  9. J. X. Chen, H. Y. Wu, and W. K. Su, Chin. Chem. Lett., 18, 536 (2007).

    Article  CAS  Google Scholar 

  10. A. Shaabani, A. Maleki, and H. Mofakham, Synth. Commun., 38, 3751 (2008).

    Article  CAS  Google Scholar 

  11. Y. X. Zong, Y. Zhao, W. C. Luo, X. H. Yu, J. K. Wang, and Y. Pan, Chin. Chem. Lett., 21, 778 (2010).

    Article  CAS  Google Scholar 

  12. J. X. Chen, W. K. Su, H. Y. Wu, M. C. Liu, and C. Jin, Green Chem., 9, 972 (2007).

    Article  CAS  Google Scholar 

  13. R. Z. Qiao, B. L. Xu, and Y. H. Wang, Chin. Chem. Lett., 18, 656 (2007).

    Article  CAS  Google Scholar 

  14. X. P. Xu, R. Jiang, X. G. Zhou, Y. Liu, S. J. Ji, and Y. Zhang, Tetrahedron, 65, 877 (2009).

    Article  CAS  Google Scholar 

  15. C. J. Xi, Y. F. Jiang, and X. H. Yang, Tetrahedron Lett., 46, 3909 (2005).

    Article  CAS  Google Scholar 

  16. J. T. Wang, X. D. Jia, L. J. Peng, and L. M. Wu, Chin. Chem. Lett., 22, 655 (2011).

    Article  CAS  Google Scholar 

  17. M. Wang, Z. G. Song, and T. T. Zhang, Chem. Heterocycl. Comp., 46, 581 (2010). [XГC, 733 (2010)].

    Article  Google Scholar 

  18. Z. Duan, X. J. Xuan, T. Li, C. F. Yang, and Y. J. Wu, Tetrahedron Lett., 47, 5433 (2006).

    Article  CAS  Google Scholar 

  19. X. H. Yang, C. J. Xi, and Y. F. Jiang, Tetrahedron Lett., 46, 8781 (2005).

    Article  CAS  Google Scholar 

  20. R. Jiang, Y. Zhang, Y. C. Shen, X. Zhu, X. P. Xu, and S. J. Ji, Tetrahedron, 66, 4073 (2010).

    Article  CAS  Google Scholar 

  21. G. Rothenberg, A. P. Downie, C. L. Raston, and J. L. Scott, J. Am. Chem. Soc., 123, 8701 (2001).

    Article  CAS  Google Scholar 

  22. H. L. Yale and M. Kalkstein, J. Med. Chem., 10, 334 (1967).

    Article  CAS  Google Scholar 

  23. S. Rostamizadeh, A. M. Amani, G. H. Mahdavinia, H. Sepehrian, and S. Ebrahimi, Synthesis, 1356 (2010).

  24. J. X. Chen, D. Z. Wu, F. He, M. C. Liu, H. Y. Wu, J. C. Ding, and W. K. Su, Tetrahedron Lett., 49, 3814 (2008).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. College of Chemistry, Chemical Engineering and Food Safety, Bohai University, Jinzhou, 121000, P. R. China

    M. Wang, J. J. Gao & L. Wang

  2. Center for Science & Technology Experiment, Bohai University, Jinzhou, 121000, P. R. China

    Z. G. Song

Authors
  1. M. Wang
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  2. J. J. Gao
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  3. Z. G. Song
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  4. L. Wang
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Corresponding author

Correspondence to M. Wang.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1039–1044, July, 2011.

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Wang, M., Gao, J.J., Song, Z.G. et al. Cerium(IV) ammonium nitrate catalyzed green synthesis of 2-substituted 2,3-dihydro- quinazolin-4(1H)-ones using a grinding technique. Chem Heterocycl Comp 47, 851–855 (2011). https://doi.org/10.1007/s10593-011-0846-5

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  • DOI: https://doi.org/10.1007/s10593-011-0846-5

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