Advertisement

Chemistry of Heterocyclic Compounds

, Volume 50, Issue 10, pp 1413–1420 | Cite as

Synthesis of Novel 4,4-Dialkyl- and 4,4-Diarylindeno[1,2-b]Thiophenes and their 2-Bromo Derivatives*

  • J. Bucevicius
  • P. Adomenasp
  • S. TumkeviciusEmail author
Article

A series of new 4,4-dialkyl- and 4,4-diaryl-4H-indeno[1,2-b]thiophenes and their 2-bromo derivatives were synthesized and characterized. An economical one-pot method for the preparation of the key starting material 2-(2-thienyl)benzoic acid and improved procedures for the synthesis of indeno[1,2-b]thiophen-4-one and 4,4-dialkyl-4H-indeno[1,2-b]thiophenes have been developed. The described methods were shown to be efficient for the preparation of the title compounds on a multigram scale.

Keywords

indeno[1,2-b]thiophenes sulfur heterocycles alkylation bromination Kumada coupling 

References

  1. 1.
    H. Choi, S. Paek, K. Lim, C. Kim, M. S. Kang, K. Song, and J. Ko, J. Mater. Chem. A., 1, 8226 (2013).CrossRefGoogle Scholar
  2. 2.
    J. J. Kim, K. Lim, H. Choi, S. Fan, M. S. Kang, G. Gao, H. S. Kang, and J. Ko, Inorg. Chem., 49, 8351 (2010).CrossRefGoogle Scholar
  3. 3.
    L. Pouchain, O. Alévêque, Y. Nicolas, A. Oger, C. H. Régent, M. Allain, P. Blanchard, and J. Roncali, J. Org. Chem., 74, 1054 (2009).CrossRefGoogle Scholar
  4. 4.
    T. C. Chao, K. T. Wong, W. Y. Hung, T. H. Hou, and W. J. Chen, Tetrahedron Lett., 50, 3422 (2009).CrossRefGoogle Scholar
  5. 5.
    C. Zhao, X. Chen, C. Gao, M. K. Ng, H. Ding, K. Park, and Y. Gao, Synth. Met., 159, 995 (2009).CrossRefGoogle Scholar
  6. 6.
    Y. Xia, Y. Gao, Y. Zhang, J. Tong, J. Li, H. Li, D. Chen, and D. Fan, Polymer, 54, 607 (2013).CrossRefGoogle Scholar
  7. 7.
    K. T. Wong, T. C. Chao, L. C. Chi, Y. Y. Chu, A. Balaiah, S. F. Chiu, Y. H. Liu, and Y. Wang, Org. Lett., 8, 5033 (2006).CrossRefGoogle Scholar
  8. 8.
    L. Cai, T. Moehl, S. J. Moon, J. D. Decoppet, R. H. Baker, Z. Xue, L. Bin, S. M. Zakeeruddin, and M. Grätzel, Org. Lett., 16, 106 (2014).CrossRefGoogle Scholar
  9. 9.
    S. Tumkevicius, J. Dodonova, K. Kazlauskas, V. Masevicius, L. Skardziute, and S. Jursenas, Tetrahedron Lett., 51, 3902 (2010).CrossRefGoogle Scholar
  10. 10.
    J. Dodonova, L. Skardziute, K. Kazlauskas, S. Jursenas, and S. Tumkevicius, Tetrahedron, 68, 329 (2012).CrossRefGoogle Scholar
  11. 11.
    L. Skardžiūtė, K. Kazlauskas, J. Dodonova, J. Bucevičius, S. Tumkevičius, and S. Juršėnas, Tetrahedron, 69, 9566 (2013).CrossRefGoogle Scholar
  12. 12.
    D. W. H. MacDowell and A. T. Jeffries, J. Org. Chem., 35, 871(1970).CrossRefGoogle Scholar
  13. 13.
    S. Sévigny and P. Forgione, Chem.-Eur. J., 19, 2256 (2013).CrossRefGoogle Scholar
  14. 14.
    C. Zhou, Q. Liu, Y. Li, R. Zhang, X. Fu, and C. Duan, J. Org. Chem., 77, 10468 (2012).CrossRefGoogle Scholar
  15. 15.
    J. R. Naber and S. L. Buchwald, Adv. Synth. Catal., 350, 957 (2008).CrossRefGoogle Scholar
  16. 16.
    R. Tatumi, T. Akita, and H. Fujihara, Chem. Commun., 3349 (2006).Google Scholar
  17. 17.
    G. Cahiez, C. Duplais, and J. Buendia, Angew. Chem., Int. Ed., 48, 6731 (2009).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  1. 1.Vilnius UniversityVilniusLithuania
  2. 2.Fine synthesis Ltd.VilniusLithuania

Personalised recommendations