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Synthesis of Novel 2-Hetarylpyrrolidines via the Reaction of N-(4,4-diethoxybutyl)amidophosphates with C-nucleophiles

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Chemistry of Heterocyclic Compounds Aims and scope

The reactions of N-(4,4-diethoxybutyl)amidophosphates with С-nucleophiles in chloroform in the presence of trifluoroacetic acid provided new 2-hetarylpyrrolidines. The reaction proceeded under mild conditions and gave good yields in the absence of metal-based catalysts.

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References

  1. Pol, S.; Corouge, M.; Vallet-Pichard, A. Hepatic Med. 2016, 8, 21.

    Article  Google Scholar 

  2. Sulkowski, M. S.; Gardiner, D. F.; Rodriguez-Torres, M.; Reddy, K. R.; Hassanein, T.; Jacobson, I.; Lawitz, E.; Lok, A. S.; Hinestrosa, F.; Thuluvath, P. J.; Schwartz, H.; Nelson, D. R.; Everson, G. T.; Eley, T.; Wind-Rotolo, M.; Huang, S.-P.; Gao, M.; Hernandez, D.; McPhee, F.; Sherman, D.; Hindes, R.; Symonds, W.; Pasquinelli, C.; Grasela, D. M.. N. Engl. J. Med. 2014, 370, 211.

    Article  CAS  Google Scholar 

  3. Feld, J. J.; Jacobson, I. M.; Hézode, C.; Asselah, T.; Ruane, P. J.; Gruener, N.; Abergel, A.; Mangia, A.; Lai, C.-L.; Chan, H. L. Y.; Mazzotta, F.; Moreno, C.; Yoshida, E.; Shafran, S. D.; Towner, W. J.; Tran, T. T.; McNally, J.; Osinusi, A.; Svarovskaia, E.; Zhu, Y.; Brainard, D. M.; McHutchison, J. G.; Agarwal, K.; Zeuzem, S.. N. Engl. J. Med. 2015, 373, 2599.

    Article  CAS  Google Scholar 

  4. Curry, M. P.; O'Leary, J. G.; Bzowej, N.; Muir, A. J.; Korenblat, K. M.; Fenkel, J. M.; Reddy, K. R.; Lawitz, E.; Flamm, S. L.; Schiano, T.; Teperman, L.; Fontana, R.; Schiff, E.; Fried, M.; Doehle, B.; An, D.; McNally, J.; Osinusi, A.; Brainard, D. M.; McHutchison, J. G.; Brown, R. S.; Charlton, M.. N. Engl. J. Med. 2015, 373, 2618.

    Article  CAS  Google Scholar 

  5. Greig, S. L. Drugs 2016, 76, 1567.

    Article  CAS  Google Scholar 

  6. Coburn, C. A.; Meinke, P. T.; Chang, W.; Fandozzi, C. M.; Graham, D. J.; Hu, B.; Huang, Q.; Kargman, S.; Kozlowski, J.; Liu, R.; McCauley, J. A.; Nomeir, A. A.; Soll, R. M.; Vacca, J. P.; Wang, D.; Wu, H.; Zhong, B.; Olsen, D. B.; Ludmerer, S. W. ChemMedChem 2013, 8, 1930.

    Article  CAS  Google Scholar 

  7. Bilello, J. P.; Lallos, L. B.; McCarville, J. F.; La Colla, M.; Serra, I.; Chapron, C.; Gillum, J. M.; Pierra, C.; Standring, D. N.; Seifer, M. Antimicrob. Agents Chemother. 2014, 58, 4431.

    Article  CAS  Google Scholar 

  8. Vince, B.; Hill, J. M.; Lawitz, E. J.; O'Riordan, W.; Webster, L. R.; Gruener, D. M.; Mofsen, R. S.; Murillo, A.; Donovan, E.; Chen, J.; McCarville, J. F.; Sullivan-Bólyai, J. Z.; Mayers, D.; Zhou, X.-J. J. Hepatol. 2014, 60, 920.

    Article  CAS  Google Scholar 

  9. Kumari, R.; Nguyen, M. H. Expert Opin. Pharmacother. 2015, 16, 739.

    Article  CAS  Google Scholar 

  10. Afdhal, N.; Zeuzem, S.; Kwo, P.; Chojkier, M.; Gitlin, N.; Puoti, M.; Romero-Gomez, M.; Zarski, J.-P.; Agarwal, K.; Buggisch, P.; Foster, G. R.; Bräu, N.; Buti, M.; Jacobson, I. M.; Subramanian, G. M.; Ding, X.; Mo, H.; Yang, J. C.; Pang, P. S.; Symonds, W. T.; McHutchison, J. G.; Muir, A. J.; Mangia, A.; Marcellin, P.. N. Engl. J. Med. 2014, 370, 1889.

    Article  Google Scholar 

  11. Kotera, J.; Mochida, H.; Inoue, H.; Noto, T.; Fujishige, K.; Sasaki, T.; Kobayashi, T.; Kojima, K.; Yee, S.; Yamada, Y.; Kikkawa, K.; Omori, K. J. Urol. 2012, 188, 668.

    Article  CAS  Google Scholar 

  12. Limin, M.; Johnsen, N.; Hellstrom, W. J. Expert Opin. Inves. Drugs 2010, 19, 1427.

    Article  Google Scholar 

  13. Kyle, J. A.; Brown, D. A.; Hill, J. K. Ann. Pharmacother. 2013, 47, 1312.

    Article  CAS  Google Scholar 

  14. Le, C.; Liang, Y.; Evans, R. W.; Li, X.; MacMillan, D. W. C. Nature 2017, 547, 79.

    Article  CAS  Google Scholar 

  15. Campos, K. R.; Klapars, A.; Waldman, J. H.; Dormer, P. G.; Chen, C.-y. J. Am. Chem. Soc. 2006, 128, 3538.

    Article  CAS  Google Scholar 

  16. Paul, A.; Seidel, D. J. Am. Chem. Soc. 2019, 141, 8778.

    Article  CAS  Google Scholar 

  17. Mandal, S.; Mahato, S.; Jana, C. K. Org. Lett. 2015, 17, 3762.

    Article  CAS  Google Scholar 

  18. Melyashova, A. S.; Smolobochkin, A. V.; Gazizov, A. S.; Voronina, J. K.; Burilov, A. R.; Pudovik, M. A. Tetrahedron 2019, 75, 130681.

    Article  Google Scholar 

  19. Polindara-García, L. A.; Montesinos-Miguel, D.; Vazquez, A. Org. Biomol. Chem. 2015, 13, 9065.

    Article  Google Scholar 

  20. Craven, P.; Aimon, A.; Dow, M.; Fleury-Bregeot, N.; Guilleux, R.; Morgentin, R.; Roche, D.; Kalliokoski, T.; Foster, R.; Marsden, S. P.; Nelson, A. Bioorg. Med. Chem. 2015, 23, 2629.

    Article  CAS  Google Scholar 

  21. Gharpure, S. J.; Vishwakarma, D. S.; Patel, R. K. Chem. Commun. 2019, 55, 6858.

    Article  CAS  Google Scholar 

  22. Smolobochkin, A. V.; Rizbayeva, T. S.; Melyashova, A. S.; Burilov, A. R.; Pudovik, M. A.; Sinyashin, O. G.; Gazizov, A. S. ChemistrySelect 2019, 4, 9322.

    Article  CAS  Google Scholar 

  23. Smolobochkin, A. V.; Rizbayeva, T. S.; Gazizov, A. S.; Voronina, J. K.; Dobrynin, A. B.; Gildebrant, A. V.; Strelnik, A. G.; Sazykin, I. S.; Burilov, A. R.; Pudovik, M. A.; Sazykina, M. A. Eur. J. Org. Chem. 2019, 5709.

  24. Smolobochkin, A.; Gazizov, A.; Sazykina, M.; Akylbekov, N.; Chugunova, E.; Sazykin, I.; Gildebrant, A.; Voronina, J.; Burilov, A.; Karchava, S.; Klimova, M.; Voloshina, A.; Sapunova, A.; Klimanova, E.; Sashenkova, T.; Allayarova, U.; Balakina, A.; Mishchenko, D. Molecules 2019, 24, 3086.

    Article  Google Scholar 

  25. Gazizov, A. S.; Kharitonova, N. I.; Smolobochkin, A. V.; Syakaev, V. V.; Burilov, A. R.; Pudovik, M. A. Monatsh. Chem. 2015, 146, 1845.

    Article  CAS  Google Scholar 

  26. Nguyen, T. B.; Wang, Q.; Guéritte, F. Eur. J. Org. Chem. 2011, 7076.

  27. Cimarelli, C.; Fratoni, D.; Mazzanti, A.; Palmieri, G. Eur. J. Org. Chem. 2011, 2094.

  28. Gravel, E.; Poupon, E.; Hocquemiller, R. Tetrahedron 2006, 62, 5248.

    Article  CAS  Google Scholar 

  29. De Kimpe, N.; Stevens, C. J. Org. Chem. 1993, 58, 2904.

    Google Scholar 

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center” of the Russian Academy of Sciences, 8 Akademika Arbuzova St, Kazan, 420088, Russia

    Andrey V. Smolobochkin, Almir S. Gazizov, Alexander R. Burilov & Mikhail A. Pudovik

  2. Kazan National Research Technological University, 68 Karla Marksa St, Kazan, 420015, Russia

    Rakhymzhan A. Turmanov

  3. Alexander Butlerov Institute of Chemistry, Kazan Federal University, 29/1 Kremlyovskaya St, Kazan, 420008, Russia

    Elizaveta A. Kuznetsova

Authors
  1. Andrey V. Smolobochkin
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  2. Rakhymzhan A. Turmanov
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  3. Almir S. Gazizov
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  4. Elizaveta A. Kuznetsova
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  5. Alexander R. Burilov
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  6. Mikhail A. Pudovik
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Correspondence to Andrey V. Smolobochkin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(10), 1363–1365

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Smolobochkin, A.V., Turmanov, R.A., Gazizov, A.S. et al. Synthesis of Novel 2-Hetarylpyrrolidines via the Reaction of N-(4,4-diethoxybutyl)amidophosphates with C-nucleophiles. Chem Heterocycl Comp 56, 1363–1365 (2020). https://doi.org/10.1007/s10593-020-02823-0

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  • DOI: https://doi.org/10.1007/s10593-020-02823-0

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