Skip to main content
SpringerLink
Log in

Synthesis of heterocycles from arylation products of unsaturated compounds: XVIII. 5-Arylfuran-2-carboxylic acids and their application in the synthesis of 1,2,4-thiadiazole, 1,3,4-oxadiazole, and [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Arylation of furan-2-carboxylic acid or its methyl ester with arenediazonium chlorides in the presence of copper(II) chloride gave the corresponding 5-arylfuran-2-carboxylic acids or methyl 5-arylfuran-2-carboxylates. 5-Arylfuran-2-carbonyl chlorides reacted with potassium thiocyanate and then with 5-methyl-1,2-oxazol-3-amine to give 5-aryl-N-[3-(2-oxopropyl)-1,2,4-thiadiazol-5-yl]furan-2-carboxamides as a result of recyclization of intermediate isoxazolylthiourea derivatives. The reactions of 5-arylfuran-2-carbonyl chlorides with 5-(2-furyl)-1H-tetrazole involved opening of the tetrazole ring with elimination of nitrogen molecule and led to the formation of 2-(5-arylfuran-2-yl)-5-(2-furyl)-1,3,4-oxadiazoles. 3-Substituted 6-(5-arylfuran-2-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles were obtained by condensation of 5-arylfuran-2-carboxylic acids with 5-substituted 4-amino-4H-1,2,4-triazole-3-thiols in phosphoryl chloride.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Obushak, N.D., Gorak, Yu.I., Matiichuk, V.S., and Lytvyn, R.Z., Russ. J. Org. Chem., 2008, vol. 44, p. 1689.

    Article  CAS  Google Scholar 

  2. Mashkovskii, M.D., Lekarstvennye sredstva (Drugs), Moscow: Novaya Volna, 2000.

    Google Scholar 

  3. Negwer, M. and Scharnow, H.-G., Organic-Chemical Drugs and Their Synonyms: An International Survey, Weinheim: Wiley, 2001, 8th ed.

    Google Scholar 

  4. Lidak, M.Yu., Khim. Geterotsikl. Soedin., 1985, p. 5.

  5. Hosoya, T., Aoyama, H., Ikemoto, T., Kihara, Y., Hiramatsu, T., Endo, M., and Suzuki, M., Bioorg. Med. Chem., 2003, vol. 11, p. 663.

    Article  CAS  Google Scholar 

  6. Huang, Q.-Q., Huang, M., Nan, F.-J., and Ye, Q.-Z., Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 5386; Ye, Q.-Z., Xie, S.-X., Huang, M., Huang, W.-J., Lu, J.-P., and Ma, Z.-Q., J. Am. Chem. Soc., 2004, vol. 126, p. 13 940.

    Article  CAS  Google Scholar 

  7. Kort, M.E., Drizin, I., Gregg, R.J., Scanio, M.J.C., Shi, L., Gross, M.F., Atkinson, R.N., Johnson, M.S., Pacofsky, G.J., Thomas, J.B., Carroll, W.A., Krambis, M.J., Liu, D., Shieh, C.-C., Zhang, X.F., Hernandez, G., Mikusa, J.P., Zhong, C., Joshi, S., Honore, P., Roeloffs, R., Marsh, K.C., Murray, B.P., Liu, J., Werness, S., Faltynek, C.R., Krafte, D.S., Jarvis, M.F., Chapman, M.L., and Marron, B.E., J. Med. Chem., 2008, vol. 51, p. 407.

    Article  CAS  Google Scholar 

  8. Lee, S., Yi, K.-Y., Hwang, S.-K., Lee, B.-H., Yoo, S.-E., and Lee, K., J. Med. Chem., 2005, vol. 48, p. 2882.

    Article  CAS  Google Scholar 

  9. Pfefferkorn, J.A., Green, M.L., Nugent, R.A., Gross, R.J., Mitchell, M.A., Finzel, B.C., Harris, M.S., Wells, P.A., Shelly, J.A., Anstadt, R.A., Kilkuskie, R.E., Kopta, L.A., and Schwende, F.J., Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 2481.

    Article  CAS  Google Scholar 

  10. Oleinik, A.F., Vozyakova, T.I., Novitskii, K.Yu., Zykova, T.N., Gus’kova, T.A., and Pershin, G.N., Khim.-Farm. Zh., 1976, no. 4, p. 46.

  11. Oleinik, A.F., Modnikova, G.A., Novitskii, K.Yu., Gus’kova, T.A., and Pershin, G.N., Khim.-Farm. Zh., 1974, no. 5, p. 7; Oleinik, A.F., Novitskii, K.Yu., Vozyakova, T.I., Gus’kova, T.A., Pershin, G.N., and Solov’eva, N.P., Khim.-Farm. Zh., 1977, no. 4, p. 27; Oleinik, A.F., Novitskii, K.Yu., Dozorova, E.N., Solov’eva, N.P., Polukhina, M.M., Novitskaya, N.A., and Pershin, G.N., Khim.-Farm. Zh., 1980, no. 9, p. 47; Oleinik, A.F., Adamskaya, E.V., Okishnevich, O.V., and Pershin, G.N., Khim.-Farm. Zh., 1983, no. 6, p. 683; Oleinik, A.F., Vozyakova, T.I., Filitis, L.N., Okinshevich, O.V., Pershin, G.N., and Shestakovskii, V.M., Pharm. Chem. J., 1984, vol. 18, p. 410.

  12. Obushak, N.D., Lesyuk, A.I., Ganushchak, N.I., Mel’nik, G.M., and Zavalii, P.Yu., Zh. Org. Khim., 1986, vol. 22, p. 2331; Pong, S.F., Pelosi, S.S., Wessels, F.L., Yu, C.-N., Burns, R.H., White, R.E., Anthony, D.R., Ellis, K.O., Wright, G.C., and White, R.L., Arzneim.-Forsch. Drug Res. II, 1983, vol. 33, p. 1411; Dombrovskii, A.V., Usp. Khim., 1984, vol. 53, p. 1625; Krutošikova, A., Zbořnik prac chemickotechnol. fakult. SVŠT 1979–1981, Bratislava, 1986, p. 15; Ref. Zh., Khim., 1987, no. 6 Zh 218.

    CAS  Google Scholar 

  13. Mathur, K.B.L. and Mehra, H.S., J. Chem. Soc., 1961, p. 2576.

  14. Khan, M.A. and Polya, J.B., Aust. J. Chem., 1973, vol. 26, p. 1147.

    CAS  Google Scholar 

  15. Krutošikova, A., Kovač, J., and Sykora, V., Collect. Czech. Chem. Commun., 1974, vol. 39, p. 1892.

    Google Scholar 

  16. Vivona, N., Cusmano, G., and Macaluso, G., J. Chem. Soc., Perkin Trans. 1, 1977, p. 1616.

  17. Huisgen, R., Sauer, J., Sturm, H.J., and Markgraf, J.H., Chem. Ber., 1960, vol. 93, p. 2106; Ollis, W.D. and Ramsden, C.A., Adv. Heterocycl. Chem., 1976, vol. 19, p. 1.

    Article  CAS  Google Scholar 

  18. Obushak, N.D., Pokhodylo, N.T., Pidlypnyi, N.I., and Matiichuk, V.S., Russ. J. Org. Chem., 2008, vol. 44, p. 1522.

    Article  CAS  Google Scholar 

  19. Rauhut, G., Adv. Heterocycl. Chem., 2001, vol. 81, p. 1.

    Article  Google Scholar 

  20. Holla, B.S., Shivananda, M.K., Akberali, P.M., Baliga, S., and Safeer, S., Farmaco, 1996, vol. 51, p. 785; Zhang, L.-X., Zhang, A.-J., Chen, X.-X., Lei, X.-X., Nan, X.-Y., Chen, D.-Y., and Zhang, Z.-Y., Molecules, 2002, vol. 7, p. 681; Zhang, Q., Pan, J., Zheng, R.-L., and Wang, Q., Pharmazie, 2005, vol. 60, p. 378; Spalińska, K., Foks, H., Kedzia, A., Wierzbowska, M., Kwapisz, E., Gebska, A., and Zilkołwska-Klinkosz, M., Phosphorus, Sulfur Silicon Relat. Elem., 2006, vol. 181, p. 609; Demirbas, N., Demirbas, A., Karaoglu, S.A., and Celik, E., Arkivoc, 2005, part (i), p. 75; Bhat, K.S., Prasad, D.J., Poojary, B., and Holla, B.S., Phosphorus, Sulfur Silicon Relat. Elem., 2004, vol. 179, p. 1595; Invidiata, F.P., Furno, G., Simoni, D., Lampronti, I., Musiu, C., Milia, C., Scintu, F., and La Colla, P., Farmaco, 1997, vol. 52, p. 259; Holla, B.S., Poojary, K.N., Rao, B.S., and Shivananda, M.K., Eur. J. Med. Chem., 2002, vol. 37, p. 511.

    CAS  Google Scholar 

  21. Obushak, N.D., Pokhodylo, N.T., Krupa, I.I., and Matiichuk, V.S., Russ. J. Org. Chem., 2007, vol. 43, p. 1223; Obushak, M.D., Pokhodylo, N.T., Ostapiuk, Yu.V., and Matiychuk, V.S., Phosphorus, Sulfur Silicon Relat. Elem., 2008, vol. 183, p. 141; Matiichuk, V.S., Pokhodilo, N.T., Krupa,I.I., and Obushak, M.D., Ukr. Bioorg. Acta, 2007, vol. 5, p. 3; Dong, H.-S. and Wang, B., J. Chin. Chem. Soc., 2005, vol. 52, p. 103; Li, D., Long, D., and Fu, H., Synth. Commun., 2005, vol. 35, p. 2495; Farghalya, A.-R., De Clercq, E., and El-Kashef, H., Arkivoc, 2006, part (x), p. 137.

    Article  CAS  Google Scholar 

  22. Krutošikova, A., Kovač, J., Rentka, J., and Čakrt, M., Collect. Czech. Chem. Commun., 1974, vol. 39, p. 767.

    Google Scholar 

  23. Burch, H.A., White, R.E., Wright, G.C., and Goldenberg, M.M., J. Pharm. Sci., 1980, vol. 69, p. 107.

    Article  CAS  Google Scholar 

  24. Glushkov, R.G., Vozyakova, T.I., Adamskaya, E.V., Gus’kova, T.A., Pushkina, T.V., Radkevich, T.P., and Solov’eva, N.P., Khim.-Farm. Zh., 1998, vol. 32,no. 1, p. 10.

    CAS  Google Scholar 

  25. Nakashima, Y., Kawashima, Y., Amanuma, F., Sota, K., Tanaka, A., and Kameyama, T., Chem. Pharm. Bull., 1984, vol. 32, p. 4271.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Ivana Franko Lviv National University, ul. Kirilla i Mefodiya 6, Lviv, 79005, Ukraine

    Yu. I. Gorak, N. D. Obushak, V. S. Matiichuk & R. Z. Lytvyn

Authors
  1. Yu. I. Gorak
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. D. Obushak
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. S. Matiichuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. R. Z. Lytvyn
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. D. Obushak.

Additional information

Original Russian Text © Yu.I. Gorak, N.D. Obushak, V.S. Matiichuk, R.Z. Lytvyn, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 4, pp. 555–563.

For communication XVII, see [1].

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gorak, Y.I., Obushak, N.D., Matiichuk, V.S. et al. Synthesis of heterocycles from arylation products of unsaturated compounds: XVIII. 5-Arylfuran-2-carboxylic acids and their application in the synthesis of 1,2,4-thiadiazole, 1,3,4-oxadiazole, and [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives. Russ J Org Chem 45, 541–550 (2009). https://doi.org/10.1134/S1070428009040125

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428009040125

Keywords

Search

Navigation