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Lewis acid catalyzed condensation of 2-aminohetarene N-oxides with N,N-dimethylformamide dimethyl acetal

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Chemistry of Heterocyclic Compounds Aims and scope

A method for the introduction of the N,N-dimethylformamidine protective group in a series of six-membered 2-aminohetarene N-oxides was developed. It was shown that 2-amino derivatives of N-oxides of various six-membered heterocycles (pyridines, pyrimidines, pyrazines, tetrazines) successfully enter the reaction. The stability of the N,N-dimethylformamidine protecting group in 2-aminohetarene N-oxides was found to depend on the type of reaction medium.

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References

  1. Makhova, N. N.; Belen'kii, L. I.; Gazieva, G. A.; Dalinger, I. L.; Konstantinova, L. S.; Kuznetsov, V. V.; Kravchenko, A. N.; Krayushkin, M. M.; Rakitin, O. A.; Starosotnikov, A. M.; Fershtat, L. L.; Shevelev, S. A.; Shirinian, V. Z.; Yarovenko, V. N. Russ. Chem. Rev. 2020, 89, 55. [Usp. Khim. 2020, 89, 55.]

  2. (a) Zlotin, S. G.; Dalinger, I. L.; Makhova, N. N.; Tartakovsky, V. A. Russ. Chem. Rev. 2020, 89, 1. [Usp. Khim. 2020, 89, 1.] (b) Gulyaev, D. A.; Klenov, M. S.; Churakov, A. M.; Strelenko, Yu. A.; Pivkina, A. N.; Tartakovsky, V. A. Russ. Chem. Bull., Int. Ed. 2021, 70, 1599. [Izv. Akad. Nauk, Ser. Khim. 2021, 1599.] (c) Zlotin, S. G.; Churakov, A. M.; Egorov, M. P.; Fershtat, L. L.; Klenov, M. S.; Kuchurov, I. V.; Makhova, N. N.; Smirnov, G. A.; Tomilov, Yu. V.; Tartakovsky, V. A. Mendeleev Commun. 2021, 31, 731.

  3. (a) Zyryanov, G. V.; Kopchuk, D. S.; Kovalev, I. S.; Santra, S.; Rahman, M.; Khasanov, A. F.; Krinochkin, A. P.; Taniya, O. S.; Chupakhin, O. N.; Charushin, V. N. Mendeleev Commun. 2020, 30, 537. (b) Sedenkova, K. N.; Nazarova, A. A.; Zverev, D. V.; Zharmuhambetova, Zh. T.; Vasilenko, D. A.; Grishin, Yu. K.; Kuznetsova, T. S.; Averina, E. B. Russ. Chem. Bull., Int. Ed. 2021, 70, 1311. [Izv. Akad. Nauk, Ser. Khim. 2021, 1311.]

  4. Volkova, Yu. M.; Makarov, A. Yu.; Pritchina, E. A.; Gritsan, N. P.; Zibarev, A. V. Mendeleev Commun. 2020, 30, 385.

    Article  CAS  Google Scholar 

  5. Das, P.; Delost, M. D.; Qureshi, M. H.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2019, 62, 4265.

    Article  CAS  Google Scholar 

  6. Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257.

    Article  CAS  Google Scholar 

  7. Koukal, P.; Ulč, J.; Nečas, D.; Kotora, M. Top. Heterocycl. Chem. 2017, 53, 29.

    Article  Google Scholar 

  8. Mfuh, A. M.; Larionov, O. V. Curr. Med. Chem. 2015, 22, 2819.

    Article  CAS  Google Scholar 

  9. Stephens, D. E.; Larionov, O. V. Top. Heterocycl. Chem. 2017, 53, 59.

    Article  Google Scholar 

  10. Kutasevich, A. V.; Perevalov, V. P.; Mityanov, V. S. Eur. J. Org. Chem. 2021, 357.

  11. Bystrov, D. M.; Zhilin, E. S.; Fershtat, L. L.; Romanova, A. A.; Ananyev, I. V.; Makhova, N. N. Adv. Synth. Catal. 2018, 360, 3157.

    Article  CAS  Google Scholar 

  12. Brown, E. V. J. Am. Chem. Soc. 1957, 79, 3565.

    Article  CAS  Google Scholar 

  13. Zhang, L.-B.; Hao, X.-Q.; Zhang, S.-K.; Liu, Z.-J.; Zheng, X.-X.; Gong, J.-F.; Niu, J.-L.; Song, M.-P. Angew. Chem., Int. Ed. 2015, 54, 272.

    Article  CAS  Google Scholar 

  14. Krasnokutskaya, E. A.; Chudinov, A. A.; Filimonov, V. D. Synthesis 2018, 1368.

  15. Kidjemet, D. Synlett 2002, 1741.

  16. Gümüş, M.; Koca, İ. ChemistrySelect 2020, 5, 12377.

    Article  Google Scholar 

  17. Wolińska, E.; Pucko, W. J. Heterocycl. Chem. 2013, 50, 590.

    Article  Google Scholar 

  18. Wolińska, E. Heterocycl. Commun. 2012, 18, 227.

    Article  Google Scholar 

  19. Wolińska, E. Heterocycl. Commun. 2016, 22, 85.

    Article  Google Scholar 

  20. Hovhannisyan, A.; Pham, T. H.; Bouvier, D.; Piroyan, A.; Dufau, L.; Qin, L.; Cheng, Y.; Melikyan, G.; Reboud-Ravaux, M.; Bouvier-Durand, M. Bioorg. Med. Chem. Lett. 2014, 24, 1571.

    Article  CAS  Google Scholar 

  21. Groom, C. R.; Bruno, I. J.; Lightfoot, M. P.; Ward, S. C. Acta Crystallogr., Sect. B 2016, 72, 171.

    Article  CAS  Google Scholar 

  22. Deady, L. W. Synth. Commun. 1977, 7, 509.

    Article  CAS  Google Scholar 

  23. Wei, H.; Gao, H.; Shreeve, J. M. Chem.–Eur. J. 2014, 20, 16943.

  24. Coburn, M. D.; Hiskey, M. A.; Lee, K.-Y.; Ott, D. G.; Stinecipher, M. M. J. Heterocycl. Chem. 1993, 30, 1593.

    Article  CAS  Google Scholar 

  25. Bruker APEX-III; Bruker AXS, Inc.: Madison, 2018.

  26. Krause, L.; Herbst-Irmer, R.; Sheldrick, G. M.; Stalke, D. J. Appl. Crystallogr. 2015, 48, 3.

    Article  CAS  Google Scholar 

  27. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Adv. 2015, A71, 3.

  28. Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, C71, 3.

    Google Scholar 

  29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Petersson, G. A.; Nakatsuji, H.; Li, X.; Caricato, M.; Marenich, A.; Bloino, J.; Janesko, B. G.; Gomperts, R.; Mennucci, B.; Hratchian, H. P.; Ortiz, J. V.; Izmaylov, A. F.; Sonnenberg, J. L.; Williams-Young, D.; Ding, F.; Lipparini, F.; Egidi, F.; Goings, J.; Peng, B.; Petrone, A.; Henderson, T.; Ranasinghe, D.; Zakrzewski, V. G.; Gao, J.; Rega, N.; Zheng, G.; Liang, W.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Throssell, K.; Montgomery, J. A. Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Millam, J. M.; Klene, M.; Adamo, C.; Cammi, R.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Farkas, O.; Foresman, J. B.; Fox, D. J. Gaussian 09, Revision D.01; Gaussian, Inc.: Wallingford, 2016.

  30. Perdew, J. P.; Ernzerhof, M.; Burke, K. J. Chem. Phys. 1996, 105, 9982.

    Article  CAS  Google Scholar 

  31. Adamo, C.; Barone, V. J. Chem. Phys. 1999, 110, 6158.

    Article  CAS  Google Scholar 

  32. Grimme, S.; Ehrlich, S.; Goerigk, L. J. Comput. Chem. 2011, 32, 1456.

    Article  CAS  Google Scholar 

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This work was carried out with the financial support of the Russian Foundation for Basic Research and the Moscow Government within the framework of the scientific project No. 21-33-70056.

X-ray structural studies and quantum-chemical calculations were carried out with the support of the Ministry of Science and Higher Education of the Russian Federation using the scientific equipment of the Center for Molecular Structure Studies of A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave, Moscow, 119991, Russia

    Sergey А. Karalash, Dmitry M. Bystrov & Leonid L. Fershtat

  2. Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow, 119991, Russia

    Sergey А. Karalash

  3. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St, Moscow, 119991, Russia

    Ivan V. Ananyev

Authors
  1. Sergey А. Karalash
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  2. Dmitry M. Bystrov
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  3. Ivan V. Ananyev
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  4. Leonid L. Fershtat
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Corresponding author

Correspondence to Leonid L. Fershtat.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(11), 1130–1136

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Karalash, S.А., Bystrov, D.M., Ananyev, I.V. et al. Lewis acid catalyzed condensation of 2-aminohetarene N-oxides with N,N-dimethylformamide dimethyl acetal. Chem Heterocycl Comp 57, 1130–1136 (2021). https://doi.org/10.1007/s10593-021-03031-0

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  • DOI: https://doi.org/10.1007/s10593-021-03031-0

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