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Synthesis and study of azide-tetrazole tautomerism in 2-azido-6-phenylpyrimidin-4(3H)-one and 2-azido-4-chloro-6-phenylpyrimidine

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Abstract

Azide-tetrazole equilibrium in 2-azido-6-phenylpyrimidin-4(3H)-one and 2-azido-4-chloro-6-phenylpyrimidine was studied by IR spectroscopy and 1H and 13C NMR spectroscopy in a comparison with the published data. For 2-azido-6-phenylpyrimidin-4(3H)-one isolated from a weakly acidic solution, 1H NMR (DMSO-d6) spectroscopy revealed a three-component equilibrium between azide (A) and tetrazole (T and T′) forms T ⇆ A ⇆ T′ (82: 10: 8) immediately after dissolution and a two-component equilibrium T ⇆ T′ (12: 88) in an equilibrium state. For the precipitate recrystallized from ethanol, the T ⇆ T′ equilibrium was observed. The structures of both tautomers were confirmed by X-ray diffraction analysis. 2-Azido-4-chloro-6-phenylpyrimidine existed predominantly in the azide form and the A ⇆ T (94: 6) equilibrium was found only in the DMSO-d6 solution.

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References

  1. A. Serbis, M. Turks, Chem. Heterocycl. Compd., 2019, 55, 1041; DOI: https://doi.org/10.1007/s10593-019-02574-7.

    Article  Google Scholar 

  2. S. Manzoor, J.-Q. Yang, Q. Tariq, H.-Z. Mei, Z.-L. Yang, Y. Hu, W.-L. Cao, V. P. Sinditskii, J.-G. Zhang, ChemistrySelect, 2020, 5, 5414; DOI: https://doi.org/10.1002/slct.202001087.

    Article  CAS  Google Scholar 

  3. N. V. Pleshkova, E. B. Nikolaenkova, V. P. Krivopalov, V. I. Mamatyuk, Russ. Chem. Bull., 2017, 66, 2095; DOI: https://doi.org/10.1007/511172-017-1986-2.

    Article  CAS  Google Scholar 

  4. E. B. Nikolaenkova, N. V. Aleksandrova, V. I. Mamatyuk, V. P. Krivopalov, Russ. Chem. Bull., 2018, 67, 893; DOI: https://doi.org/10.1007/s11172-018-2154-z.

    Article  CAS  Google Scholar 

  5. T. A. Andreeva, V. I. Eroshkin, V. P. Krivopalov, V. P. Mamaev, A. S. Trofimov, Avtometriya [Optoelectronics, Instrumentation and Data Processing], 1991, Issue 4, 3 (in Russian).

  6. T. A. Andreeva, V. I. Eroshkin, V. P. Krivopalov, E. B. Nikolaenkova, V. P. Mamaev, USSR Authors Certificate 1819004, https://www.fips.ru (in Russian).

  7. L. E. Brady, R. M. Herbst, J. Org. Chem., 1959, 24, 922; DOI: https://doi.org/10.1021/jo01089a008.

    Article  CAS  Google Scholar 

  8. C. Temple, Jr., W. C. Coburn, Jr., M. C. Thorpe, J. A. Montgomery, J. Org. Chem., 1965, 30, 2395; DOI: https://doi.org/10.1021/jo01018a069.

    Article  CAS  Google Scholar 

  9. S. Gourdain, C. Petermann, A. Martinez, D. Harakat, P. Clivio, J. Org. Chem., 2011, 76, 1906; DOI: https://doi.org/10.1021/jo102316r.

    Article  CAS  Google Scholar 

  10. S. Nag, S. Bhowmik, H. M. Gauniyal, S. Batra, Eur. J. Org. Chem., 2010, 4705; DOI: https://doi.org/10.1002/ejoc.201000586.

  11. T. S. Shestakova, Z. O. Shenkarev, S. L. Deev, O. N. Chupakhin, I. A. Khalymbadzha, V. L. Rusinov, A. S. Arseniev, J. Org. Chem., 2013, 78, 6975; DOI: https://doi.org/10.1021/jo4008207.

    Article  CAS  Google Scholar 

  12. I. A. Khalymbadzha, T. S. Shestakova, S. L. Deev, V. L. Rusinov, O. N. Chupakhin, Z. O. Shenkarev, A. S. Arseniev, Russ. Chem. Bull., 2013, 62, 521; DOI: https://doi.org/10.1007/s11172-013-0072-7.

    Article  CAS  Google Scholar 

  13. H. Kano, Y. Makisumi, Chem. Pharm. Bull., 1958, 6, 583; DOI: https://doi.org/10.1248/cpb.6.583.

    Article  CAS  Google Scholar 

  14. S. S. Kuduwa, D. Blaster, R. Boese, G. R. Desiraju, J. Org. Chem., 2001, 66, 1621; DOI: https://doi.org/10.1021/jo0013453.

    Article  Google Scholar 

  15. A. Y. Denisov, V. P. Krivopalov, V. I. Mamatyuk, V. P. Mamaev, Magn. Reson. Chem., 1988, 26, 42; DOI: https://doi.org/10.1002/mrc.1260260111.

    Article  CAS  Google Scholar 

  16. G. M. Sheldrick, Acta Crystallogr., Sect. C: Struct. Chem., 2015, 71, 3; DOI: https://doi.org/10.1107/S2053229614024218.

    Article  Google Scholar 

  17. M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. J. Su, T. L. Windus, M. Dupuis, J. A. Montgomery, J. Comput. Chem., 1993, 14, 1347; DOI: https://doi.org/10.1002/jcc.540141112.

    Article  CAS  Google Scholar 

  18. D. N. Laikov, Y. A. Ustynyuk, Russ. Chem. Bull., 2005, 54, 820; DOI: https://doi.org/10.1007/s11172-005-0329-x.

    Article  CAS  Google Scholar 

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Funding

The authors are grateful to the staff of the Multiaccess Chemical Service Center of the Siberian Branch of the Russian Academy of Sciences for spectral and analytical measurements.

This work was performed in the framework of the State Tack of NIOCH SB RAS and partially financially supported by the Ministry of Science and Higher Education of the Russian Federation (Project No. 14.W03.31.0034).

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Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation

    N. V. Aleksandrova, E. B. Nikolaenkova, Yu. V. Gatilov, D. N. Polovyanenko, V. I. Mamatyuk & V. P. Krivopalov

Authors
  1. N. V. Aleksandrova
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  2. E. B. Nikolaenkova
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  3. Yu. V. Gatilov
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  4. D. N. Polovyanenko
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  5. V. I. Mamatyuk
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  6. V. P. Krivopalov
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Corresponding authors

Correspondence to V. I. Mamatyuk or V. P. Krivopalov.

Additional information

No human or animal subjects were used in this research.

The authors declare no competing interests.

The following designations are adopted: A is the azide tautomer, T and T′ are the tetrazole tautomers.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1266–1272, June, 2022.

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Aleksandrova, N.V., Nikolaenkova, E.B., Gatilov, Y.V. et al. Synthesis and study of azide-tetrazole tautomerism in 2-azido-6-phenylpyrimidin-4(3H)-one and 2-azido-4-chloro-6-phenylpyrimidine. Russ Chem Bull 71, 1266–1272 (2022). https://doi.org/10.1007/s11172-022-3529-8

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  • DOI: https://doi.org/10.1007/s11172-022-3529-8

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