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Chemistry of Heterocyclic Compounds

, Volume 48, Issue 7, pp 1078–1084 | Cite as

Synthesis of 4H-thieno[3,2-c]chromenes by intramolecular arylation of 4-aryloxy-methyl-5-iodothiophene-2-carbaldehydes

  • A. S. Fisyuk
  • Yu. P. Bogza
  • L. V. Belyaeva
  • V. B. Belyaev
Article

The iodination of 4-chloromethylthiophene-2-carbaldehyde by N-iodosuccinimide under solvent-free conditions gives 4-chloromethyl-5-iodothiophene-2-carbaldehyde, which is used to obtain 4-aryloxy-methyl-5-iodothiophene-2-carbaldehydes. The palladium-catalyzed intramolecular cyclization of 4-aryloxymethyl-5-iodothiophene-2-carbaldehydes yields 4H-thieno[3,2-c]chromene-2-carbaldehydes.

Keywords

4-aryloxymethyl-5-iodothiophene-2-carbaldehydes 4-chloromethyl-5-iodothiophene-2-carb- aldehyde 4H-thieno[3,2-c]chromene-2-carbaldehydes intramolecular cyclization palladium catalysis 

References

  1. 1.
    Y. Makisumi, JP Pat. Appl. 48-000596; Chem. Abstr., 78, 72096u (1973). Google Scholar
  2. 2.
    Y. Makisumi, JP Pat. Appl. 49-075599; Chem. Abstr., 83, 164152r (1975). Google Scholar
  3. 3.
    C. G. Rimbault, EU Pat. Appl. 0193493. Google Scholar
  4. 4.
    S. E. Webber and J. G. Widdicombe, Agents Actions, 24, 65 (1988). CrossRefGoogle Scholar
  5. 5.
    D. F. Rogers, R. W. Godfrey, K. Castro, S. Majumdar, and P. K. Jeffery, Agents Actions, 33, 358 (1991). CrossRefGoogle Scholar
  6. 6.
    J. E. Ombetta, A. Xicluna, J. F. Robert, and J. J. Panouse, Ann. Pharm. Fr., 44, 107 (1986). Google Scholar
  7. 7.
    M. I. Hegab and M. M. Abdulla, Arch. Pharm. Chem. Life Sci., 339, 41 (2006). CrossRefGoogle Scholar
  8. 8.
    K. C. Majumdar and A. Biswas, Monatsh. Chem., 135, 1001 (2004). Google Scholar
  9. 9.
    R. A. Navarro, L. C. Bleye, A. González-Ortega, and M. C. S. Ruiz, Heterocycles, 55, 2369 (2001). CrossRefGoogle Scholar
  10. 10.
    B. Ch. Sekhar, D. V. Ramana and S. R. Ramadas, Sulfur Lett., 9, 271 (1989). Google Scholar
  11. 11.
    M. Weißenfels, A. Hantschmann, T. Steinführer, and E. Birkner, Z. Chem., 29, 166 (1989). CrossRefGoogle Scholar
  12. 12.
    M. Darbarwar and V. Sundaramurthy, Synthesis, 337 (1982). Google Scholar
  13. 13.
    K. T. Potts, M. O. Dery, and W. A. Juzukonis, J. Org. Chem., 54, 1077 (1989). CrossRefGoogle Scholar
  14. 14.
    K. T. Potts and M. O. Dery, J. Chem. Soc., Chem. Commun., 561 (1986). Google Scholar
  15. 15.
    H. Gotthardt and O. M. Huss, Liebigs Ann. Chem., 347 (1981). Google Scholar
  16. 16.
    N. D. Heindel, J. A. Minatelli, and D. Harris, J. Org. Chem., 42, 1465 (1977). CrossRefGoogle Scholar
  17. 17.
    A. H. Lamberton and R. E. Paine, J. Chem. Soc., Perkin Trans. 1, 683 (1976). Google Scholar
  18. 18.
    T. Yao, D. Yue, and R. C. Larock, J. Org. Chem., 70, 9985 (2005). CrossRefGoogle Scholar
  19. 19.
    B. H. Lipshutz, F. Kayser, and N. Maullin, Tetrahedron Lett., 35, 815 (1994). CrossRefGoogle Scholar
  20. 20.
    E. M. Beccalli, G. Broggini, M. Martinelli, and S. Sottocornola, Synthesis, 136 (2008). Google Scholar
  21. 21.
    L. Katsiel, A. N. Sharipova, and A. S. Fisyuk, Mendeleev Commun., 18, 169 (2008). CrossRefGoogle Scholar
  22. 22.
    E. M. Beccalli, G. Broggini, M. Martinelli, G. Paladino, and C. Zoni, Eur. J. Org. Chem., 2091 (2005). Google Scholar
  23. 23.
    F. Bellina and R. Rossi, Tetrahedron, 65, 10269 (2009). CrossRefGoogle Scholar
  24. 24.
    Ya. L. Gol'dfarb, I. B. Karmanova, Yu. B. Vol'kenshtein, and L. I. Belen'kii, Khim. Geterotsikl. Soedin., 1474 (1978). [Chem. Heterocycl. Compd., 14, 1196 (1978)]. Google Scholar

Copyright information

© Springer Science+Business Media New York 2012

Authors and Affiliations

  • A. S. Fisyuk
    • 1
  • Yu. P. Bogza
    • 1
  • L. V. Belyaeva
    • 1
  • V. B. Belyaev
    • 1
  1. 1.F. M. Dostoevskii Omsk State UniversityOmskRussia

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