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Pyrrolo[2,3-d]pyrimidine derivatives in the synthesis of a novel heterocyclic system 2a,5a,7-triazaacenaphthylene

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Chemistry of Heterocyclic Compounds Aims and scope

A convenient method for the synthesis of methyl 8-oxo-3H,8H-2a,5a,7-triazaacenaphthylene-2-carboxylate by iodination of 7-allyl-4-methoxypyrrolo[2,3-d]pyrimidine-6-carboxylic acid methyl ester followed by elimination of hydrogen iodide has been developed. The use of 4-methoxypyrrolo[2,3-d]pyrimidine-6-carboxylic acid as the starting compound led to the formation of iodomethylpyrimido[5',4':4,5]-pyrrolo[2,1-c][1,4]oxazine, a promising precursor for the synthesis of a new tricyclic system based on pyrrolo[2,3-d]pyrimidine.

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References

  1. Gentile, G.; Di Fabio, R.; Pavone, F.; Sabbatini, F. M.; St-Denis, Y.; Zampori, M. G.; Vitulli, G.; Worby, A. Bioorg. Med. Chem. Lett. 2007, 17, 5218.

    Article  CAS  PubMed  Google Scholar 

  2. Dyck, B.; Grigoriadis, D. E.; Gross, R. S.; Guo, Z.; Haddach, M.; Marinkovic, D.; McCarthy, J. R.; Moorjani, M.; Regan, C. F.; Saunders, J.; Schwaebe, M. K.; Szabo, T.; Williams, J. P.; Zhang, X.; Bozigian, H.; Chen, T. K.J. Med. Chem. 2005, 48, 4100.

    Article  CAS  PubMed  Google Scholar 

  3. Biedenbach, D. J.; Bouchillon, S. K.; Hackel, M.; Miller, L. A.; Scangarella-Oman, N. E.; Jakielaszek, C.; Sahm, D. F. Antimicrob. Agents Chemother. 2016, 60, 1918.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Golparian, D.; Jacobsson, S.; Unemo, M.; Scangarella-Oman, N. J. Antimicrob. Chemother. 2018, 73, 2072.

    Article  CAS  PubMed  Google Scholar 

  5. Kawamoto, T.; Tomimatsu, K.; Ikemoto, T.; Abe, H.; Hamamura, K.; Takatani, M. Tetrahedron Lett. 2000, 41, 3447.

    Article  CAS  Google Scholar 

  6. Chui, W.-K.; Dolzhenko, A. V.; Dolzhenko, A. V. Heterocycles 2007, 71, 2049.

    Article  Google Scholar 

  7. Sun, H.; Zhou, H.; Khorev, O.; Jiang, R.; Yu, T.; Wang, X.; Du, Y.; Ma, Y.; Meng, T.; Shen, J. J. Org. Chem. 2012, 77, 10745.

    Article  CAS  PubMed  Google Scholar 

  8. Azimov, V. A.; Bychikhina, N. N.; Yakhontov, L. N. Chem. Heterocycl. Compd. 1982, 18, 1061. [Khim. Geterotsikl. Soedin. 1982, 1370.]

    Article  Google Scholar 

  9. Erion, M. D.; Niwas, S.; Rose, J. D.; Ananthan, S.; Allen, M.; Secrist, J. A.; Babu, S.; Bugg, C. E.; Guida W.; Ealick, S. E.; Montgomery, J. A. J. Med. Chem. 1993, 36, 3771.

    Article  CAS  PubMed  Google Scholar 

  10. Rosemeyer, H.; Kretschmer, U.; Seela, F. Helv. Chim. Acta 1985, 68, 2165.

    Article  CAS  Google Scholar 

  11. Verves, E. V.; Kucher, A. V.; Muzychka, L. V.; Smolii, O. B. Chem. Heterocycl. Compd. 2013, 48, 1844. [Khim. Geterotsikl. Soedin. 2012, 1968.]

    Article  CAS  Google Scholar 

  12. Yaremchuk, I. O.; Muzychka, L V.; Smolii, O. B.; Kucher, O. V.; Shishkina, S. V. Tetrahedron Lett. 2018, 59, 442.

    Article  CAS  Google Scholar 

  13. Muzychka, L.V.; Yaremchuk, I. O.; Muzychka, O. V.; Smolii, O. B. Fr.-Ukr. J. Chem. 2017, 5, 15.

    CAS  Google Scholar 

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Correspondence to Oleg B. Smolii.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(4/5), 397–400

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Muzychka, L.V., Yaremchuk, I.O., Verves, E.V. et al. Pyrrolo[2,3-d]pyrimidine derivatives in the synthesis of a novel heterocyclic system 2a,5a,7-triazaacenaphthylene. Chem Heterocycl Comp 55, 397–400 (2019). https://doi.org/10.1007/s10593-019-02471-z

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  • DOI: https://doi.org/10.1007/s10593-019-02471-z

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