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Synthesis of New Furo[2,3-b]pyridine and Furo[3,2-d]pyrimidine Derivatives

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Abstract

New furo[2,3-b]pyridine and pyrido[3′,2′:4,5]furo[3,2-d]pyrimidine derivatives were synthesized from ethyl 5-alkyl-1-amino-6,7,8,9-tetrahydrofuro[2,3-c]isoquinoline-2-carboxylates. Reactions of ethyl 5-alkyl-1-[(aminoacetyl)amino]-6,7,8,9-tetrahydrofuro[2,3-c]isoquinoline-2-carboxylates with hydrazine hydrate in¬volved not only cyclization but also hydrazinolysis and elimination of the acyl group.

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References

  1. Sirakanyan, S.N., Hovakimyan, A.A., and Nora-vyan, A.S., Russ. Chem. Rev., 2015, vol. 84, p. 441. doi 10.1070/RCR4447

    Article  CAS  Google Scholar 

  2. Dorsey, B.D., McDonough, C., McDaniel, S.L., Levin, R.B., Newton, C.L., Hoffman, J.M., Darke, P.L., Zugay-Murphy, J.A., Emini, E.A., Schleif, W.A., Olsen, D.B., Stahlhut, M.W., Rutkowski, C.A., Kuo, L.C., Lin, J.H., Chen, I-W., Michelson, S.R., Holloway, M.K., Huff, J.R., and Vacca, J.P., J. Med. Chem., 2000, vol. 43, p. 3386. doi 10.1021/jm9903848

    Article  CAS  Google Scholar 

  3. Schnute, M.E., Brideau, R.J., Collier, S.A., Cudahy, M.M., Hopkins, T.A., Knechtel, M.L., Oien, N.L., Sackett, R.S., Scott, A., Stephan, M.L., Wathen, M.W., and Wieber, J.L., Bioorg. Med. Chem. Lett., 2008, vol. 18, p. 3856. doi 10.1016/ j.bmcl.2008.06.060

    Article  CAS  Google Scholar 

  4. Martin, M.W., Newcomb, J., Nunes, J.J., Bemis, J.E., McGowan, D.C., White, R.D., Buchanan, J.L., DiMauro, E.F., Boucher, C., Faust, T., Hsieh, F., Huang, X., Lee, J.H., Schneider, S., Turcib, S.M., and Zhu, X., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 2299. doi 10.1016/j.bmcl.2007.01.048

    Article  CAS  Google Scholar 

  5. Debenham, J.S., Madsen-Duggan, C.B., Toupence, R.B., Walsh, T.F., Wanga, J., Tong, X., Kumar, S., Lao, J., Fong, T.M., Xiao, J.C., Huang, C., Shen, C., Feng, Y., Marsh, D.J., Shearman, L.P., Strack, A.M., and Goulet, M.T., Bioorg. Med. Chem. Lett, 2010, vol. 20, p. 1448. doi 10.1016/j.bmcl.2009.12.065

    Article  CAS  Google Scholar 

  6. Martins, C., Carreiras, M.C., Leon, R., Rios, C., Bartolini, M., Andrisano, V., Iriepa, I., Moraleda, I., Galvez E., García, M., Egea, J., Samadi, A., Chioua, M., and Marco-Contelles, J., Eur. J. Med. Chem., 2011, vol. 46, p. 6119. doi 10.1016/ j.ejmech.2011.09.038

    Article  CAS  Google Scholar 

  7. Dinakaran, V.S. and Srinivasan, K.K., Pharma Chem., 2011, vol. 3, p. 62.

    CAS  Google Scholar 

  8. Hayakawa, M., Kaizawa, H., Moritomo, H., Koizumi, T., Ohishi, T., Yamano, M., Okada, M., Ohta, M., Tsukamoto, S., Raynaud, F.I., Workman, P., Water-field, M.D., and Parker, P., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 2438. doi 10.1016/j.bmcl.2007.02.032

    Article  CAS  Google Scholar 

  9. Feng, L., Reynisdottir, I., and Reynisson, J., Eur. J. Med. Chem., 2012, vol. 54, p. 463. doi 10.1016/ j.ejmech.2012.05.029

    Article  CAS  Google Scholar 

  10. Taltavull, J., Serrat, J., Gracia, J., Gavalda, A., Cordoba, M., Calama, E., Montero, J.L., Andres, M., Miralpeix, M., Vilella, D., Hernández, B., Beleta, J., Ryder, H., and Pages, L., Eur. J. Med. Chem., 2011, vol. 46, p. 4946. doi 10.1016/j.ejmech.2011.07.054

    Article  CAS  Google Scholar 

  11. Sirakanyan, S.N., Spinelli, D., Geronikaki, A., and Hovakimyan, A.A., Tetrahedron, 2015, vol. 71, p. 7638. doi 10.1016/j.tet.2015.07.069

    Article  CAS  Google Scholar 

  12. Sirakanyan, S.N., Spinelli D., Geronikaki A., Kartsev, V.G., Hakobyan, E.K., and Hovakimyan, A.A., Tetrahedron Lett., 2016, vol. 57, p. 5338. doi 10.1016/ j.tetlet.2016.10.058

    Article  CAS  Google Scholar 

  13. Sirakanyan, S.N., Spinelli, D., Geronikaki, A., Kartsev, V.G., Hakobyan, E.K., and Hovakimyan, A.A., ChemistrySelect, 2018, vol. 3, p. 10938. doi 10.1002/slct.201802221

    Article  CAS  Google Scholar 

  14. Sirakanyan, S.N., Kartsev, V.G., Hovakimyan, A.A., Noravyan, A.S., and Shakhatuni, A.A., Chem. Heterocycl. Compd., 2013, vol. 48, p. 1676. doi 10.1007/s10593-013-1192-6

    Article  CAS  Google Scholar 

  15. Sirakanyan, S.N., Geronikaki A., Spinelli, D., Hovakimyan, A.A., and Noravyan, A.S., Tetrahedron, 2013, vol. 69, p. 10637. doi 10.1016/j.tet.2013.10.015

    Article  CAS  Google Scholar 

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Funding

This study was performed under financial support by the State Science Committee of the Ministry of Education and Science of Armenia in the framework of research project no. 18T-1D170.

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Correspondence to S. N. Sirakanyan.

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Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 9, pp. 1433–1439.

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Sirakanyan, S.N., Hakobyan, E.K. & Hovakimyan, A.A. Synthesis of New Furo[2,3-b]pyridine and Furo[3,2-d]pyrimidine Derivatives. Russ J Org Chem 55, 1344–1350 (2019). https://doi.org/10.1134/S1070428019090136

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  • DOI: https://doi.org/10.1134/S1070428019090136

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