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β-(Cycloalkylamino)ethanesulfonyl azides as novel water-soluble reagents for the synthesis of diazo compounds and heterocycles

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Chemistry of Heterocyclic Compounds Aims and scope

Novel water-soluble sulfonyl azides were synthesized, which are basic by nature. The obtained compounds were used as donors of the diazo group in the diazo transfer reaction. Due to their good solubility in water and high polarity, the byproducts formed in this case were easily separated from the desired products by washing with water or column chromatography. It was also shown that new sulfonyl azides as a result of reactions can be incorporated in heterocyclic products, imparting them water solubility.

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References

  1. Comprehensive Organic Name Reactions and Reagents; Wang, Z., Ed.; John Wiley & Sons, Inc., 2010, p. 2322.

  2. Shafran, Y.; Glukhareva, T.; Dehaen, W; Bakulev, V Adv. Heterocycl. Chem. 2018, 126, 109.

    Article  CAS  Google Scholar 

  3. Belyaev, N.; Beryozkina, T.; Bakulev, V. Chem. Heterocycl. Compd. 2016, 52, 206. [Khim. Geterotsikl. Soedin.2016, 52, 206.]

  4. Beliaev, N. A.; Shafikov, M. Z.; Efimov, I. V.; Beryozkina, T. V.; Lubec, G.; Dehaen, W.; Bakulev, V. A. New J. Chem.2018, 42, 7049.

    Article  CAS  Google Scholar 

  5. Bakulev, V. A.; Beryozkina, T.; Thomas, J.; Dehaen, W. Eur. J. Org. Chem.2018, 3, 262.

    Article  Google Scholar 

  6. Dyachenko, V. D.; Dyachenko, I. V.; Nenajdenko, V. G. Russ. Chem. Rev. 2018, 87, 1. [Usp. Khim.2018, 87, 1.]

  7. Belskaya, N.; Subbotina, J.; Lesogorova, S. Top Heterocycl. Chem.2015, 40, 51.

    Article  CAS  Google Scholar 

  8. Jagodzinski, T. S. Chem. Rev. 2002, 103, 197.

    Article  Google Scholar 

  9. Baum, J. S.; Shook, D. A.; Davies, H. M. L.; Smith, H. D. Synth. Comm.1987, 17, 1709.

    Article  CAS  Google Scholar 

  10. Hazen, F. W. B. G. G.; Roberts, F. E.; Russ, W. K.; Seman, J. J.; Staskiewicz, S. Org. Synth. 1996, 73, 144.

  11. Green, G. M.; Peet, N. P.; Metz, W. A. J. Org. Chem. 2001, 66, 2509.

    Article  CAS  Google Scholar 

  12. Potter, G. T.; Jayson, G. C.; Miller, G. J.; Gardiner, J. M. J. Org. Chem. 2016, 81, 3443.

    Article  CAS  Google Scholar 

  13. Hendrickson, J. B.; Wolf, W. A. J. Org. Chem. 1968, 33, 3610.

    Article  CAS  Google Scholar 

  14. O'Mahony, R. M.; Broderick, C. M.; Lynch, D.; Collins, S. G.; Maguire, A. R. Tetrahedron Lett. 2019, 60, 35.

    Article  CAS  Google Scholar 

  15. Dar'in, D.; Kantin, G.; Krasavin, M. Chem. Commun.2019, 55, 5239.

    Article  CAS  Google Scholar 

  16. Taber, D. F.; Ruckle, R. E.; Hennessy, M. J. J. Org. Chem. 1986, 51, 4077.

    Article  CAS  Google Scholar 

  17. Filimonov, V. O.; Dianova, L. N.; Galata, K. A.; Beryozkina, T. V.; Novikov, M. S.; Berseneva, V. S.; Eltsov, O. S.; Lebedev, A. T.; Slepukhin, P. A.; Bakulev, V. A. J. Org. Chem.2017, 82, 4056.

    Article  CAS  Google Scholar 

  18. Namelikonda, N. K.; Manetsch, R. Chem. Commun. 2012, 48, 1526.

    Article  CAS  Google Scholar 

  19. Davies, W. G.; Hardisty, E. W.; Nevell, T. P.; Peters, R. H. J. Chem. Soc. B1970, 998.

  20. (a) Jiang, Y.; Khong, V. Zh. Yu.; Lourdusamy, E.; Park, Ch.-M. Chem. Commun. 2012, 48, 3133. (b) Ghosh, D. Synth. Commun. 1991, 21, 191. (c) Benati, L.; Montevecchi, P. C.; Spagnolo, P. Gazz. Chim. Ital. 1992, 122, 249. (d) Chen, X.; Xie, Y.; Xiao, X.; Li, G.; Deng, Yu.; Jiang, H.; Zeng, W. Chem. Commun. 2015, 51, 15328. (e) Presset, M.; Mailhol, D.; Coquerel, Y.; Rodriguez, J. Synthesis2011, 2549. (f) Sharpe, R. J.; Malinowski, J. T.; Johnson, J. S. J. Am. Chem. Soc.2013, 135, 17990. (g) Chiara, J. L.; Suarez, J. R. Adv. Synth. Cat.2011, 353, 575. (h) Rianelli, R. De S.; De Souza, M. C. B. V.; Ferreira, V. F. Synth. Commun.2004, 34, 951. (i) Ramachary, D. B.; Narayana, V. V.; Ramakumar, K. Tetrahedron Lett. 2008, 49, 2704. (j) Kitamura, M.; Tashiro, N.; Okauchi, T. Synlett2009, 2943. (k) Kitamura, M.; Tashiro, N.; Miyagawa, S.; Okauchi, T. Synthesis2011, 1037. (l) Muthyala, M. K.; Choudhary, S.; Kumar, A. J. Org. Chem. 2012, 77, 8787.

  21. (a) Shved, A. S.; Tabolin, A. A.; Novikov, R. A.; Nelyubina, Yu. V.; Timofeev, V. P.; Ioffe, S. L. Eur. J. Org. Chem.2016, 2016, 5569. (b) Dutra, L. G.; Saibert, C.; Vicentini, D. S.; Sá, M. M. J. Mol. Catal. A: Chem.2014, 386, 35. (c) Zhu, Sh.; Jin, G.; Xu, Y. Tetrahedron2003, 59, 4389. (d) Boddy, A. J.; Affron, D. P.; Cordier, Ch. J.; Rivers, E. L.; Spivey, A. C.; Bull, J. A. Angew. Chem., Int. Ed. 2019, 131, 1472. (e) Debbarma, S.; Sk, M. R.; Modak, B.; Maji, M. Sudan J. Org. Chem. 2019, 84, 6207. (f) Madan K. Synth. Commun. 1991, 21, 2121. (g) Lynch, D.; O'Mahony, R. M.; McCarthy, D. G.; Bateman, L. M.; Collins, S. G.; Maguire, A. R. Eur. J. Org. Chem. 2019, 2019, 3575.

  22. Dankova, E. F.; Bakulev, V. A.; Krut'ko, D. P. Chem. Heterocycl. Compd.1991, 27, 607. [Khim. Geterotsikl. Soedin.1991, 860.]

  23. Dianova, L. N.; Berseneva, V. S.; Eltsov, O. S.; Fan, Z. J.; Bakulev, V. A. Chem. Heterocycl. Compd.2014, 50, 972. [Khim. Geterotsikl. Soedin.2014, 1055.]

  24. Bakulev, V. A.; Dehaen, W. The Chemistry of 1,2,3-Thiadiazoles; John Wiley & Sons Inc., 2004, p. 241.

  25. Stadler, D.; Anschüts, W.; Regitz, M.; Keller, G.; van Assche, D.; Fleury, J.-P. Liebigs Ann. Chem. 1975, 12, 2159.

    Article  Google Scholar 

  26. Clark, J.; Parvizi P.; Southon, I. W. J. Chem. Soc., Perkin Trans. 11976, 125.

  27. Hansen, J. B.; Oorwalo, F. Z. Canadian Patent CA 2289099 A1.

  28. Cocco, M.T.; Onnis, V. Synthesis1993, 199.

  29. Cocco, M. T.; Congiu, C.; Maccioni, A.; Plumitallo, A. J. Heterocycl. Chem. 1989, 26, 1859.

    Article  CAS  Google Scholar 

  30. Brown, T.; Kadir, K.; Mackenzie, G.; Shaw, G. J. Chem. Soc., Perkin Trans. 1 (1972–1999)1979, 3107.

  31. Kantlehner, W. Sci. Synth. 2006, 24, 337.

    Google Scholar 

  32. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.

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The authors thank the Russian Science Foundation (Project No. 18-13-00161) for financial support. Special thanks to Leonid Dobrolyubskii for the illustration.

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Authors and Affiliations

  1. Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St, Yekaterinburg, 620002, Russia

    Yuri M. Shafran, Pavel S. Silaichev & Vasiliy A. Bakulev

  2. Perm State National Research University, 15 Bukireva St, Perm, 614990, Russia

    Pavel S. Silaichev

  3. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St, Yekaterinburg, 620990, Russia

    Vasiliy A. Bakulev

Authors
  1. Yuri M. Shafran
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  2. Pavel S. Silaichev
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  3. Vasiliy A. Bakulev
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Correspondence to Vasiliy A. Bakulev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(12), 1251–1261

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Shafran, Y.M., Silaichev, P.S. & Bakulev, V.A. β-(Cycloalkylamino)ethanesulfonyl azides as novel water-soluble reagents for the synthesis of diazo compounds and heterocycles. Chem Heterocycl Comp 55, 1251–1261 (2019). https://doi.org/10.1007/s10593-019-02609-z

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