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Synthesis and reactions of 5-aryl-2-thiophenecarbaldehydes

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of 2-thiophenecarbaldehyde with arene diazonium chlorides in the presence of CuCl2 catalyst gave 5-aryl-2-thiophenecarbaldehydes. Use of 4-nitrobenzene diazonium chloride in the reaction also gave the isomeric 3-(4-nitrophenyl)-2-thiophenecarbaldehyde. Condensation products of the 5-aryl-2-thiophenecarbaldehydes with cyanoacetic acid esters, cyanoacetamide, and with barbituric and dimethylbarbituric acids were prepared.

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References

  1. M. D. Obushak, V. V. Kaepyak, Y. V. Ostapiuk, and V. S. Matiychuk, Phosph. Sulfur, Silicon Relat. Elem., 182, 1437 (2007).

    Article  CAS  Google Scholar 

  2. K. H. Saunders and R. L. Allen, Aromatic Diazo compounds, Edward Arnold, London (1985), p. 594.

    Google Scholar 

  3. H. Zollinger, Diazo Chemistry. I. Aromatic and Heteroaromatic Compounds, VCH, Weinheim (1994), p. 243.

    Google Scholar 

  4. C. S. Rondestvedt, in: Organic Reactions, Vol. 24, John Wiley, New York, London (1976), p. 225.

    Google Scholar 

  5. N. D. Obushak, A. I. Lesyuk, N. I. Ganuschak, G. M. Mel'nik, and Yu. P. Zavalii, Zh. Org. Khim, 22, 2331 (1986).

    CAS  Google Scholar 

  6. N. D. Obushak, N. I. Ganuschak, A. I. Lesyuk, L. M. Dzikovskaya, and P. P. Kisilitsa, Zh. Org. Khim., 26, 873 (1990).

    CAS  Google Scholar 

  7. A. F. Oleinik, T. I. Vozyakova, G. A. Modnikova, and K. Yu. Novitskii, Khim. Geterotsikl. Soedin., 441 (1972). [Chem. Heterocycl. Comp., 8, (1972)].

    Google Scholar 

  8. D. Balachari, L. Quinn, and G. A. O'Doherty, Tetrahedron Lett., 40, 4769 (1999).

    Article  CAS  Google Scholar 

  9. S. Holla, R. Gonsalves, and S. Shenoy, Eur. J. Med. Chem., 35, 267 (2000).

    Article  CAS  Google Scholar 

  10. T. Noguchi, M. Hasegawa, K. Tomisawa, and M. Mitsukuchi, Bioorg. Med. Chem., 11, 4729 (2003).

    Article  CAS  Google Scholar 

  11. M. Michaelides, Y. Hong, S. DiDomenico, E. K. Bayburt, K. E. Asin, D. R. Britton, C. Wel Lin, and K. Shiosaki, J. Med. Chem., 40, 1585 (1997).

    Article  CAS  Google Scholar 

  12. A. Tanaka, T. Terasawa, H. Hagihara, Y. Sakuma, N. Ishibe, M. Sawada, H. Takasugi, and H. Tanaka, J. Med. Chem., 41, 2390 (1998).

    Article  CAS  Google Scholar 

  13. T. Hosoya, H. Aoyama, T. Ikemoto, Y. Kihara, T. Hiramatsu, M. Endo, and M. Suzuki, Bioorg. Med. Chem., 11, 663 (2003).

    Article  CAS  Google Scholar 

  14. D. A. Alonso, C. Náera, and M. C. Pacheco, J. Org. Chem., 67, 5588 (2002).

    Article  CAS  Google Scholar 

  15. T. E. Barder and S. L. Buchwald, Org. Lett., 6, 2649 (2004).

    Article  CAS  Google Scholar 

  16. T. Itahara, J. Org. Chem., 50, 5272 (1985).

    Article  CAS  Google Scholar 

  17. R. Frimm, L. Fišera, and J. Kovać, Collect. Czech. Chem. Commun., 38, 1809 (1973).

    CAS  Google Scholar 

  18. L. Racane, V. Tralić-Kulenović, D. W. Boykin, and G. Karminski-Zamola, Molecules, 8, 342 (2003).

    Article  CAS  Google Scholar 

  19. L. Racane, V. Tralić-Kulenović, G. Karminski-Zamola, and L. Fišer-Jakić, Monatsh. Chem., 126, 1375 (1995).

    CAS  Google Scholar 

  20. V. K. Kul'nevich, P. A. Pavlov, and G. D. Krapivin, Khim. Geterotsikl. Soedin., 1169 (1986). [Chem. Heterocycl. Comp., 22, 943 (1986)].

    Google Scholar 

  21. S. Fisichella, G. Mineri, G. Scarlata, and D. Sciotto, Tetrahedron, 31, 2445 (1975).

    Article  CAS  Google Scholar 

  22. W. Hanefeld and M. Schlitzer, J. Heterocycl. Chem., 32, 1019 (1995).

    Article  CAS  Google Scholar 

  23. C. M. Beaton, N. B. Chapman, K. Clarke, and J. M. Willis, J. Chem. Soc., Perkin Trans. 1, 2355 (1976).

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Authors and Affiliations

  1. Ivano Franko Lviv National University, Lviv, 79005, Ukraine

    M. D. Obushak, V. S. Matiychuk & R. Z. Lytvyn

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  1. M. D. Obushak
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  2. V. S. Matiychuk
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  3. R. Z. Lytvyn
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Correspondence to M. D. Obushak.

Additional information

Communication 16 in the series “Synthesis of heterocycles based on the products of arylation of unsaturated compounds”. For Communication 15 see [1].

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1166–1171, August, 2008.

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Obushak, M.D., Matiychuk, V.S. & Lytvyn, R.Z. Synthesis and reactions of 5-aryl-2-thiophenecarbaldehydes. Chem Heterocycl Comp 44, 936–940 (2008). https://doi.org/10.1007/s10593-008-0135-0

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  • DOI: https://doi.org/10.1007/s10593-008-0135-0

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