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Synthesis of hybrid compounds by benzylation of acylhydrazones with 3,5-di-tert-butyl-4-hydroxybenzyl acetate

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Abstract

N-Benzylation of acylhydrazones of the hydroxybenzaldehyde series with 3,5-di-tert-butyl-4-hydroxybenzyl acetate was performed at room temperature in the absence of acid or base catalysts. Carboxamides do not react with 3,5-di-tert-butyl-4-hydroxybenzyl acetate under similar conditions. N-Benzylation of isoniazid and (diphenylphosphoryl)acetic acid hydrazones was shown to be an efficient method for the synthesis of new hybrid compounds containing moieties of biologically active acylhydrazones and sterically hindered phenols. N-Benzyl derivatives of isoniazid and (diphenylphosphoryl)acetic acid hydrazones containing a hydroxy group at the ortho position of the aromatic ring are formed as individual E isomers with respect to the C-N double bond.

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References

  1. Design of Hybrid Molecules for Drug Development, Ed. M. Decker, Elsevier, 2017, 352 pp; DOI: https://doi.org/10.1016/B978-0-08-101011-2.00012-X.

  2. Yu. G. Shtyrlin, A. S. Petukhov, A. D. Strelnik, N. V. Shtyrlin, A. G. Iksanova, M. V. Pugachev, R. S. Pavelyev, M. S. Dzyurkevich, M. R. Garipov, K. V. Balakin, Russ. Chem. Bull., 2019, 68, 911; DOI: https://doi.org/10.1007/s11172-019-2504-5.

    Article  CAS  Google Scholar 

  3. L. Yu. Ukhin, L. G. Kuz’mina, D. V. Alexeenko, L. V. Belousova, A. S. Morkovnik, E. N. Shepelenko, V. A. Podshibyakin, G. S. Borodkin, O. I. Dmitrieva, Russ. Chem. Bull., 2019, 68, 2290; DOI: https://doi.org/10.1007/s11172-019-2702-1.

    Article  CAS  Google Scholar 

  4. E. B. Menshchikova, V. Z. Lankin, N. V. Kandalintseva, Fenol’nye antioksidanty v biologii i meditsine lPhenolic Antioxidants in Biology and Medicine], Saarbrücken (Germany), LAP LAMBERT Academic Publishing, 2013, 488 pp. (in Russian).

    Google Scholar 

  5. Yu. N. Oludina, A. D. Voloshina, M. V. Kulik, V. V. Zobov, S. V. Bukharov, R. G. Tagasheva, G. N. Nugumanova, A. R. Burilov, M. A. Kravchenko, S. N. Skornyakov, G. L. Rusinov, Pharm. Chem. J. (Engl. Transl.), 2014, 48, 5; DOI: https://doi.org/10.1007/s11094-014-1032-8.

    Article  CAS  Google Scholar 

  6. A. V. Bogdanov, I. F. Zaripova, A. D. Voloshina, A. S. Strobykina, N. V. Kulik, S. V. Bukharov, V. F. Mironov, Russ. J. Gen. Chem., 2018, 88, 57; DOI: https://doi.org/10.1134/S1070363218010097.

    Article  CAS  Google Scholar 

  7. A. V. Bogdanov, I. F. Zaripova, A. D. Voloshina, A. S. Strobykina, N. V. Kulik, S. V. Bukharov, J. K. Voronina, A. R. Khamatgalimov, V. F. Mironov, Monatsh. Chem. 2018, 149, 111; DOI: https://doi.org/10.1007/s00706-017-2049-y.

    Article  CAS  Google Scholar 

  8. A. V. Bogdanov, I. F. Zaripova, A. D. Voloshina, A. S. Sapunova, N. V. Kulik, S. V. Bukharov, J. K. Voronina, A. E. Vandyukov, V. F. Mironov, ChemistrySelect, 2019, 4, 6162; DOI: https://doi.org/10.1002/slct.201901708.

    Article  CAS  Google Scholar 

  9. Pat. RF 2457212, Byul. Izobret. [Invent. Bull.], 2012, 21 (in Russian).

  10. I. Semina, E. Shilovskay, R. Tarasova, A. Baychourina, V. Pavlov, N. Thickhonova, R. Garaev, Phosphorus, Sulfur, Silicon, Relat. Elem., 1999, 144–146, 753; DOI: https://doi.org/10.1080/10426509908546354.

    Article  Google Scholar 

  11. R. I. Tarasova, V. V. Moskva, Russ. J. Gen. Chem., 1997, 67, 1393.

    CAS  Google Scholar 

  12. I. I. Semina, V. P. Balashov, T. V. Kurmysheva, R. I. Tarasova, E. V. Shilovskaya, O. V. Voskresenskaya, A. Z. Baichurina, M. I. Al’myasheva, Pharm. Chem. J. (Engl. Transl.), 2013, 47, 28; DOI: https://doi.org/10.1007/s11094-013-0889-2.

    Article  CAS  Google Scholar 

  13. V. P. Balashov, M. I. Al’myasheva, R. I. Tarasova, I. F. Rusina, N. P. Kul’kova, T. V. Kurmysheva, O. V. Voskresenskaya, Eksp. Klin. Farm. [Exp. Clin. Pharm.], 2007, 70, 30 (in Russian).

    CAS  Google Scholar 

  14. S. V. Bukharov, Yu. N. Oludina, R. A. Khabibullina, A. R. Burilov, E. L. Gavrilova, I. A. Krutov, R. G. Tagasheva, Phosphorus, Sulfur, Silicon, Relat. Elem., 2018, 193, 822; DOI: https://doi.org/10.1080/10426507.2018.1515205.

    Article  CAS  Google Scholar 

  15. S. V. Bukharov, R. A. Khabibullina, N. I. Akylbekov, I. A. Litvinov, O. A. Lodochnikova, A. B. Dobrynin, A. G. Strelnik, A. R. Burilov, I. A. Krutov, E. L. Gavrilova, Synth. Commun., 2020, 50, 41; DOI: https://doi.org/10.1080/00397911.2019.1681453.

    Article  CAS  Google Scholar 

  16. S. V. Bukharov, G. N. Nugumanova, N. A. Mukmeneva, A. R. Burilov, E. M. Kasymova, M. A. Pudovik, A. I. Konovalov, Russ. J. Org. Chem., 2004, 40, 293.

    CAS  Google Scholar 

  17. G. N. Nugumanova, I. A. Litvinov, A. T. Gubaidullin, A. V. Chernova, R. R. Shagidullin, S. V. Bukharov, N. A. Mukmeneva, Russ. J. Struct. Chem., 2006. 47, 791; DOI: https://doi.org/10.1007/s10947-006-0373-x.

    Article  CAS  Google Scholar 

  18. J. March, Advanced Organic Chemistry. Reactions, Mechanisms and Structure, Wiley-Intersci. Publ., Jon Wiley and Sons, New York, 1985, 1346 pp.

    Google Scholar 

  19. N. Sinha, S. Jain, A. Tilekar, R. S. Upadhayaya, N. Kishore, R. K. Sinhab, S.K. Aroraa, ARKIVOC, 2005, 9; DOI: https://doi.org/10.3998/ark.5550190.0006.202.

  20. S. V. Bukharov, R. A. Khabibullina, N. I. Akylbekov, I. A. Litvinov, O. A. Lodochnikova, A. B. Dobrynin, A. G. Strelnik, A. R. Burilov, I. A. Krutov, E. L. Gavrilova, Synth. Commun., 2020, 50, 41, DOI: https://doi.org/10.1080/00397911.2019.1681453.

    Article  CAS  Google Scholar 

  21. P. Foster, F. Weinhold, J. Am. Chem. Soc., 1980, 102, 7211; DOI: https://doi.org/10.1021/ja00544a007.

    Article  CAS  Google Scholar 

  22. D. Becke, Phys. Rev. A, 1988, 38, 3098; DOI: https://doi.org/10.1103/PhysRevA.38.3098.

    Article  CAS  Google Scholar 

  23. J. P. Perdew, K. Burke, Y. Wang, Phys. Rev. B, 1996, 54, 16533; DOI: https://doi.org/10.1103/PhysRevB.54.16533.

    Article  CAS  Google Scholar 

  24. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Jr. Montgomery, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian09, Gaussian, Inc., Wallingford CT, 2009.

    Google Scholar 

  25. S. V. Bukharov, R. G. Tagasheva, G. N. Nugumanova, L. V. Mavromati, Vestn. Kazan. Tekhnol. Univ. [Bull. Kazan Technol. Univ.], 2010, 6, 54 (in Russian).

    Google Scholar 

  26. N. V. Loginova, T. V. Koval’chuk, A. T. Gres, N. P. Osipovich, G. I. Polozov, Yu. S. Halauko, Y. V. Faletrov, H. I. Harbatsevich, A. V. Hlushko, I. I. Azarko, Yu. V. Bokshits, Polyhedron, 2015, 88, 125; DOI: https://doi.org/10.1016/j.poly.2014.12.014.

    Article  CAS  Google Scholar 

  27. J. R. Dimmocka, S. C. Vashishtha, J. P. Stables, Eur. J. Med. Chem., 2000, 35, 241; DOI: https://doi.org/10.1016/S0223-5234(00)00123-9.

    Article  Google Scholar 

  28. S. V. Bukharov, Yu. N. Oludina, R. A. Khabibullina, A. R. Burilov, E. L. Gavrilova, I. A. Krutov, R. G. Tagasheva, Phosphorus, Sulfur, Silicon, Relat. Elem., 2018, 193, 822; DOI: https://doi.org/10.1080/10426507.2018.1515205.

    Article  CAS  Google Scholar 

  29. R. I. Tarasova, O. V. Voskresenskaya, I. I. Semina, T. V. Kurmysheva, V. P. Balashov, V. V. Moskva, Pharm. Chem. J. (Engl. Transí.), 2002, 36, 298; DOI: https://doi.org/10.1023/A:1020872422070.

    Article  CAS  Google Scholar 

  30. G. M. Sheldrick, SADABS, Bruker AXS Inc., Madison, USA, 1997.

    Google Scholar 

  31. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Adv. 2015, 71, 3; DOI: https://doi.org/10.1107/S2053273314026370.

    Article  Google Scholar 

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

    Article  Google Scholar 

  33. L. J. Farrugia, J. Appl. Crystallogr. 2012, 45, 849; DOI: https://doi.org/10.1107/S0021889812029111.

    Article  CAS  Google Scholar 

  34. A. L. Spek, Acta Crystallogr. Sect. D, 2009, 65, 148; DOI: https://doi.org/10.1107/S090744490804362X.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Kazan National Research Technological University, 68 ul. K. Marksa, 420015, Kazan, Russian Federation

    S. V. Bukharov, D. F. Bakhdyrova & R. G. Tagasheva

  2. A. E. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of Russian Academy of Sciences”, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    A. R. Burilov & I. A. Litvinov

  3. Kazan Federal University, 18 ul. Kremlevskaya, 420008, Kazan, Russian Federation

    D. V. Chachkov & Ya. A. Vereshchagina

Authors
  1. S. V. Bukharov
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  2. D. F. Bakhdyrova
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  3. R. G. Tagasheva
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  4. A. R. Burilov
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  5. I. A. Litvinov
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  6. D. V. Chachkov
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Correspondence to R. G. Tagasheva.

Additional information

Based on the materials of the II Scientific Conference “Dynamic Processes in the Chemistry of Organoelement Compounds” dedicated to the 75th anniversary of A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences (November 11–13, 2020, Kazan, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1964–1972, October, 2021.

This study was financially supported by the Russian Foundation for Basic Research and the Cabinet of Ministers of the Republic of Tatarstan (Grant 18-43-160004).

Quantum chemical calculations (performed by D. V. Chachkov) were financially supported within the framework of the state assignment for the Research Institute of Systemic Research of the Russian Academy of Sciences.

This paper does not contain descriptions of studies on animals or humans.

The authors declare no competing interests.

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Bukharov, S.V., Bakhdyrova, D.F., Tagasheva, R.G. et al. Synthesis of hybrid compounds by benzylation of acylhydrazones with 3,5-di-tert-butyl-4-hydroxybenzyl acetate. Russ Chem Bull 70, 1964–1972 (2021). https://doi.org/10.1007/s11172-021-3304-2

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