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Iodine-catalyzed synthesis of pyrazolo[4,3-f]quinoline derivatives via a highly regio-selective Povarov reaction

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Abstract

A highly regio-selective Povarov reaction of an aromatic aldehyde, 1H-indazol-5-amine, and methyl 3-oxobutanoate catalyzed by iodine is described. This novel reaction selectively gave 3H-pyrazolo[4,3-f]quinolin-9-yl acetates, in high yield, rather than 3H-pyrazolo[4,3-f]quinoline-8-carboxylate derivatives. This procedure has the advantages of mild reaction conditions, high yields, metal-free catalyst, and high regio-selectivity.

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References and notes

  1. P. Muthumani, S. Venkataraman, R. Meera, G. Nayak, N. Chidambaranathan, P. Devi, B. Kameswari, Pharm. Chem. 2, 385 (2010)

    CAS  Google Scholar 

  2. J. Nayak, K.S. Girish, M. Babu, B. Kalluraya, Indian J. Heterocycl. Chem. 19, 105 (2009)

    CAS  Google Scholar 

  3. S.F. Thakor, D.M. Patel, M.P. Patel, R.G. Patel, Saudi Pharm. J. 15, 48 (2007)

    CAS  Google Scholar 

  4. A. Al-Qahtani, Y.M. Siddiqui, A.A. Bekhit, O.A. El-Sayed, H.Y. Aboul-Enein, M.N. Al-Ahdal, Arch. Pharm. 338, 484 (2005)

    Article  CAS  Google Scholar 

  5. A. Danel, E. Gondek, I. Kityk, Opt. Mater. 32, 267 (2009)

    Article  CAS  Google Scholar 

  6. E. Gondek, A. Danel, B. Kwiecien, J. Sanetra, A.V. Kityk, Spectrochim. Acta A. 74A, 685 (2009)

    CAS  Google Scholar 

  7. I. Fuks-Janczarek, R. Miedzinski, E. Gondek, P. Szlachcic, I.V. Kityk, J. Mater. Sci. 19, 434 (2008)

    CAS  Google Scholar 

  8. I. Fuks-Janczarek, K. Danel, I.V. Kityk, B. Kwiecien, Mater. Chem. Phys. 111, 69 (2008)

    Article  CAS  Google Scholar 

  9. E. Gondek, A. Danel, I.V. Kityk, J. Lumin. 128, 348 (2008)

    Article  CAS  Google Scholar 

  10. E. Gondek, J. Sanetra, M. Mac, A. Danel, I. Fuks-Janczarek, Opt. Mater. 30, 939 (2008)

    Article  CAS  Google Scholar 

  11. L.S. Povarov, Russ. Chem. Rev. 36, 65 (1967)

    Article  Google Scholar 

  12. V.V. Kouznetsov, Tetrahedron 65, 2721 (2009)

    Article  CAS  Google Scholar 

  13. X.F. Lin, S.L. Cui, Y.G. Wang, Tetrahedron Lett. 47, 3127 (2006)

    Article  CAS  Google Scholar 

  14. X.S. Wang, Q. Li, J.R. Wu, S.J. Tu, J. Comb. Chem. 11, 433 (2009)

    Article  CAS  Google Scholar 

  15. X.S. Wang, Q. Li, J.R. Wu, Y.L. Li, C.S. Yao, S.J. Tu, Synthesis 1902 (2008)

  16. X.S. Wang, J. Zhou, M.Y. Yin, K. Yang, S.J. Tu, J. Comb. Chem. 12, 266 (2010)

    Article  Google Scholar 

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Acknowledgments

We are grateful to a Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions, Qing Lan Project (10QLD008) and Graduate Foundation (CXLX12_0984) of Jiangsu Education Committee for financial support.

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Authors and Affiliations

  1. The Key Laboratory of Biotechnology on Medical Plant of Jiangsu Province, Jiangsu Normal University, Xuzhou, 221116, Jiangsu, People’s Republic of China

    Mei-Mei Zhang

  2. School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, 221116, Jiangsu, People’s Republic of China

    Wei Wang, Tuan-Jie Li, Chang-Sheng Yao & Xiang-Shan Wang

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  1. Mei-Mei Zhang
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  2. Wei Wang
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  3. Tuan-Jie Li
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  5. Xiang-Shan Wang
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Correspondence to Xiang-Shan Wang.

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Zhang, MM., Wang, W., Li, TJ. et al. Iodine-catalyzed synthesis of pyrazolo[4,3-f]quinoline derivatives via a highly regio-selective Povarov reaction. Res Chem Intermed 39, 1781–1787 (2013). https://doi.org/10.1007/s11164-012-0712-9

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  • DOI: https://doi.org/10.1007/s11164-012-0712-9

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