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Novel Method of Synthesis of 2,3-Dihydro-Furo[3,2-h]Quinolines

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Chemistry of Heterocyclic Compounds Aims and scope

Reaction of 8-hydroxy-7-piperidinomethylquinoline with pyridinium ylides gave 2-acyl-2,3-dihydro-furo[3,2-h]quinolines. The formation of a highly electrophilic quinoline type o-quinone methide is proposed as an intermediate.

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References

  1. R. C. Schnur, US Pat. Appl. 4176185.

  2. P. A. Cruickshank, F. T. Lee, and A. Lupichuk, J. Med. Chem., 13, 1110 (1970).

    Article  CAS  Google Scholar 

  3. A. Arrault, G. Guillaumet, J.-M. Leger, C. Jarry, and J.-Y. Merour, Synthesis, 1879 (2002).

  4. I. Yavari and Z. Hossaini, Tetrahedron Lett., 46, 4465 (2006).

    Article  Google Scholar 

  5. H. Meinhold, M. Muhlstadt, and R. M. Muslih, J. Prakt. Chem., 331, 136 (1989).

    Article  CAS  Google Scholar 

  6. H. Togo and O. Kikuchi, Heterocycles, 28, 373 (1989).

    Article  CAS  Google Scholar 

  7. H. Timmler and H. Andersag, DE Pat. Appl. 937588.

  8. S. Malik, U. K. Nadir, and P. S. Pandey, Tetrahedron, 65, 3918 (2009).

    Article  CAS  Google Scholar 

  9. Y. Han, H. Hou, R. Yao, Q. Fu, and C.-G. Yan, Synthesis, 4061 (2010).

  10. C.-P. Chuang and A.-I. Tsai, Synthesis, 675 (2006).

  11. V. A. Osyanin, E. A. Ivleva, and Y. N. Klimochkin, Synth. Commun, 42, 1832 (2012).

    Article  CAS  Google Scholar 

  12. V. A. Osyanin, D. V. Osipov, and Yu. N. Klimochkin, Khim. Geterotsikl. Soedin., 469 (2010). [Chem. Heterocycl. Compd., 46, 377 (2010)].

    Google Scholar 

  13. Q.-F. Wang, X.-K. Song, J. Chen, and C.-G. Yan, J. Comb. Chem., 11, 1007 (2009).

    Article  CAS  Google Scholar 

  14. C. G. Stuckwisch, Synthesis, 469 (1973).

  15. J. H. Burckhalter and R. I. Leib, J. Org. Chem., 26, 4078 (1961).

    Article  CAS  Google Scholar 

  16. F. Krohnke, Chem. Ber., 69, 921 (1936).

    Google Scholar 

  17. K. Ohga, Y. Takashima, H. Takahashi, Y. Kawaguchi, H. Yamaguchi, and A. Harada, Macromolecules (Washington, DC, U. S.), 38, 5897 (2005).

    CAS  Google Scholar 

  18. Y.-M. Shen, P.-C. Lv, W. Chen, P.-G. Liu, M.-Z. Zhang, and H.-L. Zhu, Eur. J. Med. Chem., 45, 3184 (2010).

    Article  CAS  Google Scholar 

  19. W. G. Phillips and K. W. Ratts, J. Org. Chem., 35, 3144 (1970).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Samara State Technical University, 244 Molodogvardeiskaya St., Samara, 443100, Russia

    V. A. Osyanin, D. V. Osipov & Yu. N. Klimochkin

Authors
  1. V. A. Osyanin
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  2. D. V. Osipov
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  3. Yu. N. Klimochkin
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Correspondence to V. A. Osyanin.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1069-1072 , July, 2012.

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Osyanin, V.A., Osipov, D.V. & Klimochkin, Y.N. Novel Method of Synthesis of 2,3-Dihydro-Furo[3,2-h]Quinolines. Chem Heterocycl Comp 48, 993–996 (2012). https://doi.org/10.1007/s10593-012-1090-3

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  • DOI: https://doi.org/10.1007/s10593-012-1090-3

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