Advertisement

Chemistry of Heterocyclic Compounds

, Volume 46, Issue 1, pp 50–55 | Cite as

Synthesis of heterocycles on the basis of arylation products of unsaturated compounds. 19.* Arylation of 2-acetylthio- phene and the synthesis of 2-(5-aryl-2-thien- yl)-4-quinolinecarboxylic acids

  • V. S. Matiychuk
  • N. D. ObushakEmail author
  • R. Z. Lytvyn
  • Yu. I. Horak
Article

The reaction of 2-acetylthiophene with acetylthiophene with arenediazonium chlorides in the presence of cupric chloride as catalyst gives 2-acetyl-5-arylthiophenes. These products react with 5-chloro- and 5-bromoisatins to give 6-chloro- and 6-bromo-substituted 2-(5-aryl-2-thienyl)-4-quinolinecarboxylic acids.

Keywords

2-acetyl-5-arylthiophenes 2-acetylthiophene 4-quinolinecarboxylic acid derivatives arylation Meerwein reaction Pfitzinger reaction 

References

  1. 1.
    R. L. Martyak, N. D. Obushak, and V. S. Matiichuk, Zh. Org. Khim., 45, 555 (2009).Google Scholar
  2. 2.
    A. V. Dombrovskii, Usp. Khim., 53, 1625 (1984).Google Scholar
  3. 3.
    K. H. Saunders and R. L. Allen, Aromatic Diazo Compounds, Edward Arnold, London (1985).Google Scholar
  4. 4.
    H. Zollinger, Diazo Chemistry. 1. Aromatic and Heteroaromatic Compounds, VCH, Weinheim, Germany (1994), p. 243.Google Scholar
  5. 5.
    C. S. Rondestvedt, in: Organic Reactions, vol. 24, John Wiley, New York-London (1976), p. 225.Google Scholar
  6. 6.
    N. D. Obushak, A. I. Lesyuk, N. I. Ganushchak, G. M. Mel’nik, and Yu. P. Zavalii, Zh. Org. Khim., 22, 2331 (1986).Google Scholar
  7. 7.
    N. D. Obushak, N. I. Ganushchak, A. I. Lesyuk, L. M. Dzikovskaya, and P. P. Kisilitsa, Zh. Org. Khim., 26, 873 (1990).Google Scholar
  8. 8.
    A. F. Oleinik, T. I. Vozyakova, G. A. Modnikova, and K. Yu. Novitskii, Khim. Geterotsikl. Soedin., 441 (1972). [Chem. Heterocycl. Soedin., 8, 402 (1972)].Google Scholar
  9. 9.
    N. D. Obushak, V. S. Matiichuk, and R. Z. Lytvyn, Khim. Geterotsikl. Soedin., 1166 (2008). [Chem. Heterocycl. Chem., 44, 936 (2008)].Google Scholar
  10. 10.
    R. Frimm, L. Fišera, and J. Kovač, Collect. Czech. Chem. Commun., 38, 1809 (1973).Google Scholar
  11. 11.
    L. Racane, V. Tralić-Kulenovic, D. W. Boykin, and G. Karminski-Zamola, Molecules, 8, 342 (2003).CrossRefGoogle Scholar
  12. 12.
    L. Racane, V. Tralić-Kulenović, G. Karminski-Zamola, and L. Fišer-Jakić, Monatsh. Chem., 126, 1375 (1995).CrossRefGoogle Scholar
  13. 13.
    D. R. Shridhar, C. V. Reddy Sastry, S. C. Chaturvedi, R. Gurumurthy, P. P. Singh, C. Seshagiri Rao, and A. Y. Junnarkar, Indian J. Chem., 23B, 692 (1984).Google Scholar
  14. 14.
    S. Kotha, K. Chakraborty, and E. Brachmachary, Synlett, 1621 (1999).Google Scholar
  15. 15.
    K. M. Lawson Daku, R. F. Newton, S. P. Pearce, J. Vile, and J. M. J. Williams, Tetrahedron Lett., 44, 5095 (2003).CrossRefGoogle Scholar
  16. 16.
    K. Arentsen, S. Caddick, F. G. N. Cloke, A. P. Herring, and P. B. Hitchcock, Tetrahedron Lett., 45, 3511 (2004).CrossRefGoogle Scholar
  17. 17.
    I. R. Baxendale, C. M. Griffiths-Jones, S. V. Ley, and G. K. Tranmer, Chem. Eur. J., 12, 4407 (2006).CrossRefGoogle Scholar
  18. 18.
    A. Battace, M. Lemhadri, T. Zair, H. Doucet, and M. Santelli, Adv. Synth. Cat., 349, 2507 (2007).CrossRefGoogle Scholar
  19. 19.
    T. Itahara, J. Org. Chem., 50, 5272 (1985).CrossRefGoogle Scholar
  20. 20.
    N. D. Obushak, Yu. I. Gorak, V. S. Matiichuk, and R. Z. Lytvyn, Zh. Org. Khim., 44, 1712 (2008).Google Scholar
  21. 21.
    M.-G. A. Shvekhgeimer, Khim. Geterotsikl. Soedin., 323 (2004). [Chem. Heterocycl. Comp., 40, 257 (2004)].Google Scholar
  22. 22.
    J. F. M. da Silva, S. J. Garden, and A. C. Pinto, J. Braz. Chem. Soc., 12, 273 (2001).Google Scholar
  23. 23.
    M. D. Mashkovskii, Drugs [in Russian], Novaya Volna, Moscow (2000).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2010

Authors and Affiliations

  • V. S. Matiychuk
    • 1
  • N. D. Obushak
    • 1
    Email author
  • R. Z. Lytvyn
    • 1
  • Yu. I. Horak
    • 1
  1. 1.Ivan Franko Lviv National UniversityLvivUkraine

Personalised recommendations