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Synthesis and Azido-Tetrazole Tautomerism of New Methylsulfanyl Thieno[3,2-d]pyrimidine Derivatives

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Abstract

New 7-amino, 7-azido, and 7-alkylsulfanyl derivatives have been synthesized from 7-chloro-9-(methylsulfanyl)-4-(propan-2-yl)-2,3-dihydro-1H-cyclopenta[4′,5′]pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine. 7-Azido-9-(methylsulfanyl)-4-(propan-2-yl)-2,3-dihydro-1H-cyclopenta[4′,5′]pyrido[3′,2′:4,5]thieno[3,2-d]-pyrimidine has been found to exist in solution as a mixture of azido and tetrazole tautomers, whereas only its tetrazole form is present in the crystalline state.

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References

  1. Taltavull, J., Serrat, J., Gracia, J., Gavalda, A., Andres, M., Cordoba, M., Miralpeix, M., Vilella, D., Beleta, J., Ryder, H., and Pages, L., J. Med. Chem., 2010, vol. 53, p. 6912. https://doi.org/10.1021/jm100524j

    Article  CAS  Google Scholar 

  2. Agarwal, A., Louise-May, S., Thanassi, J.A., Podos, S.D., Cheng, J., Thoma, C., Liu, C., Wiles, J.A., Nelson, D.M., Phadke, A.S., Bradbury, B.J., Deshpande, M.S., and Pucci, M.J., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 2807. https://doi.org/10.1016/j.bmcl.2007.02.056

    Article  CAS  Google Scholar 

  3. Sirakanyan, S.N., Spinelli, D., Geronikaki, A., Kartsev, V.G., Hakobyan, E.K., and Hovakimyan, A.A., Synth. Commun., 2019, vol. 49, p. 1262. https://doi.org/10.1080/00397911.2019.1595659

    Article  CAS  Google Scholar 

  4. Sirakanyan, S.N., Geronikaki, A., Domenico, S., Hakobyan, E.K., Kartsev, V.G., Petrou, A., and Hovakimyan, A.A., Ann. Acad. Bras. Ciênc., 2018, vol. 90, p. 1043. https://doi.org/10.1590/0001-3765201820170798

    Article  CAS  Google Scholar 

  5. Kjellerup, L., Gordon, S., Cohrt, K.O., Brown, W.D., Fuglsang, A.T., and Winther, A.-M.L., Antimicrob. Agents Chemother., 2017, vol. 61, p. 1. https://doi.org/10.1128/aac.00032-17

    Article  Google Scholar 

  6. Sirakanyan, S.N., Akopyan, E.K., Paronikyan, R.G., Akopyan, A.G., and Ovakimyan, A.A., Pharm. Chem. J., 2016, vol. 50, p. 296. https://doi.org/10.1007/s11094-016-1439-5

    Article  CAS  Google Scholar 

  7. Sirakanyan, S.N., Ovakimyan, A.A., Noravyan, A.S., Dzhagatspanyan, I.A., Shakhatuni, A.A., Nazaryan, I.M., and Akopyan, A.G., Pharm. Chem. J., 2013, vol. 47, p. 130. https://doi.org/10.1007/s11094-013-0910-9

    Article  CAS  Google Scholar 

  8. Sirakanyan, S.N., Spinelli, D., Geronikaki, A., Kartsev, V.G., Hakobyan, E.K., Panosyan, H.A., Stepanyan, H.M., Zuppiroli, L., and Hovakimyan, A.A., Curr. Org. Chem., 2017, vol. 21, p. 1227. https://doi.org/10.2174/1385272821666170222102400

    Article  CAS  Google Scholar 

  9. Sirakanyan, S.N., Spinelli, D., Geronikaki, A., Panosyan, H.A., and Hovakimyan, A.A., Curr. Org. Chem., 2016, vol. 20, p. 1350. https://doi.org/10.2174/1385272820666151116213645

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  11. Sirakanyan, S.N., Spinelli, D., Geronikaki, A., Kartsev, V.G., Panosyan, H.A., Ayvazyan, A.G., Tamazyan, R.A., Frenna, V., and Hovakimyan, A.A., Tetrahedron, 2016, vol. 72, p. 1919. https://doi.org/10.1016/j.tet.2016.02.048

    Article  CAS  Google Scholar 

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Correspondence to S. N. Sirakanyan.

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The authors declare the absence of conflict of interests.

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 12, pp. 1843–1849.

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Sirakanyan, S.N., Hakobyan, E.K. & Hovakimyan, A.A. Synthesis and Azido-Tetrazole Tautomerism of New Methylsulfanyl Thieno[3,2-d]pyrimidine Derivatives. Russ J Org Chem 55, 1840–1846 (2019). https://doi.org/10.1134/S1070428019120054

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  • DOI: https://doi.org/10.1134/S1070428019120054

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