Russian Chemical Bulletin

, Volume 64, Issue 1, pp 112–126 | Cite as

Continuous-flow catalytic hydrogenation of 3a,6-epoxyisoindoles

  • V. P. ZaytsevEmail author
  • F. I. Zubkov
  • D. F. Mertsalov
  • D. N. Orlova
  • E. A. Sorokina
  • E. V. Nikitina
  • A. V. Varlamov
Full Articles


Selective catalytic (10% Pd/C) hydrogenation of the double bond in the oxabicyclo[2.2.1]heptene fragment of substituted fused 1-oxo-3a,6-epoxyisoindoles is described. A continuous-flow hydrogenation device that incorporates in situ hydrogen generation by electrolysis of water was used. Changing the hydrogen source from water to deuterium oxide provides possibility to synthesize deuterated oxoepoxyisoindolones. Hydrogenation is stereoselective to give exclusively exo-cis deuterated derivatives.


continuous-flow reactor heterogeneous catalytic hydrogenation reduction 3a,6-epoxyisoindoles deuteration 


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  1. 1.
    G. Ertl, H. Knözinger, F. Schüth, J. Weitkamp, Handbook of Heterogeneous Catalysis, Wiley–VCH, Weinheim, 2008, 4270 pp.CrossRefGoogle Scholar
  2. 2.
    S. Nishimura, Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis, Wiley–Intersci., New York, 2001, 700 pp.Google Scholar
  3. 3.
    G. V. Smith, F. Notheisz, Heterogenous Catalysis in Organic Chemistry, Academic Press, New York, 1999, 346 pp.Google Scholar
  4. 4.
    P. N. Rylander, Hydrogenation Methods, Academic Press, New York, 1985, 477 pp.Google Scholar
  5. 5.
    M. Bartók, Stereochemistry of Heterogeneous Metal Catalysis, Wiley, Chichester, 1985, 632 pp.Google Scholar
  6. 6.
    P. N. Rylander, Catalytic Hydrogenation in Organic Synthesis, Academic Press, New York, 1979, 325 pp.Google Scholar
  7. 7.
    M. Freifelder, Catalytic Hydrogenation in Organic Synthesis–Procedures and Commentary, Wiley–Intersci., New York, 1978, 191 pp.Google Scholar
  8. 8.
    G. Domán, L. Kocsis, R. Jones, F. Darvas, J. Chem. Health Safety, 2013, 20, 3.CrossRefGoogle Scholar
  9. 9.
    M. Irfan, E. Petricci, T. N. Glasnov, M. Taddei, C. O. Kappe, Eur. J. Org. Chem., 2009, 1327.Google Scholar
  10. 10.
    R. V. Jones, L. Godorhazy, N. Varga, D. Szalay, L. Urge, F. Darvas, J. Comb. Chem., 2006, 8, 110.CrossRefGoogle Scholar
  11. 11.
    A. V. Varlamov, E. V. Boltukhina, F. I. Zubkov, N. V. Sidorenko, A. I. Chernyshev, D. G. Grudinin, Chem. Heterocycl. Compd. (Engl. Transl.), 2004, 40, 22 [Khim. Geterotsikl. Soedin., 2004, 27].CrossRefGoogle Scholar
  12. 12.
    F. I. Zubkov, V. P. Zaytsev, E. V. Nikitina, V. N. Khrustalev, S. V. Gozun, E. V. Boltukhina, A. V. Varlamov, Tetrahedron, 2011, 67, 9148.CrossRefGoogle Scholar
  13. 13.
    V. P. Zaytsev, N. M. Mikhailova, I. K. Airiyan, E. V. Galkina, V. D. Golubev, E. V. Nikitina, F. I. Zubkov, A. V. Varlamov, Chem. Heterocycl. Compd. (Engl. Transl.), 2012, 48, 505 [Khim. Geterotsikl. Soedin., 2012, 538].CrossRefGoogle Scholar
  14. 14.
    F. I. Zubkov, V. P. Zaytsev, E. S. Puzikova, E. V. Nikitina, V. N. Khrustalev, R. A. Novikov, A. V. Varlamov, Chem. Heterocycl. Compd. (Engl. Transl.), 2012, 48, 514 [Khim. Geterotsikl. Soedin., 2012, 549].CrossRefGoogle Scholar
  15. 15.
    F. I. Zubkov, V. P. Zaytsev, I. K. Airiyan, V. D. Golubev, E. S. Puzikova, E. A. Sorokina, E. V. Nikitina, A. V. Varlamov, Russ. Chem. Bull. (Int. Ed.), 2012, 61, 600 [Izv. Akad. Nauk, Ser. Khim., 2012, 598].CrossRefGoogle Scholar
  16. 16.
    F. I. Zubkov, V. P. Zaitsev, A. S. Peregudov, N. M. Mikhailova, A. V. Varlamov, Russ. Chem. Bull. (Int. Ed.), 2007, 56, 1063 [Izv. Akad. Nauk, Ser. Khim., 2007, 1023].CrossRefGoogle Scholar
  17. 17.
    V. P. Zaytsev, F. I. Zubkov, F. A. A. Toze, D. N. Orlova, M. N. Eliseeva, D. G. Grudinin, E. V. Nikitina, A. V. Varlamov, J. Heterocycl. Chem., 2013, 50, S1, E18.Google Scholar
  18. 18.
    F. I. Zubkov, V. P. Zaitsev, A. M. Piskareva, M. N. Eliseeva, E. V. Nikitina, N. M. Mikhailova, A. V. Varlamov, Russ. J. Org. Chem. (Engl. Transl.), 2010, 46, 1192 [Zh. Org. Khim., 2010, 46, 1191.CrossRefGoogle Scholar
  19. 19.
    F. I. Zubkov, J. D. Ershova, A. A. Orlova, V. P. Zaytsev, E. V. Nikitina, A. S. Peregudov, A. V. Gurbanov, R. S. Borisov, V. N. Khrustalev, A. M. Maharramov, A. V. Varlamov, Tetrahedron, 2009, 65, 3789.CrossRefGoogle Scholar
  20. 20.
    F. I. Zubkov, T. R. Galeev, E. V. Nikitina, I. V. Lazenkova, V. P. Zaytsev, A. V. Varlamov, Synlett, 2010, 14, 2063.CrossRefGoogle Scholar
  21. 21.
    F. I. Zubkov, E. V. Nikitina, T. R. Galeev, V. P. Zaytsev, V. N. Khrustalev, R. A. Novikov, D. N. Orlova, A. V. Varlamov, Tetrahedron, 2014, 70, 1659.CrossRefGoogle Scholar
  22. 22.
    F. I. Zubkov, I. K. Airiyan, J. D. Ershova, T. R. Galeev, V. P. Zaytsev, E. V. Nikitina, A. V. Varlamov, RSC Adv., 2012, 2, 4103.CrossRefGoogle Scholar
  23. 23.
    H. W. Gschwend, M. J. Hillman, B. Kisis, J. Org. Chem., 1976, 41, 104.CrossRefGoogle Scholar
  24. 24.
    T. Mukaiyama, N. Iwasawa, Chem. Lett., 1981, 29.Google Scholar
  25. 25.
    R. Pedrosa, S. Sayalero, M. Vicente, B. Casado, J. Org. Chem., 2005, 70, 7273.CrossRefGoogle Scholar
  26. 26.
    C.-C. Wang, W.-D. Z. Li, J. Org. Chem., 2012, 77, 4217.CrossRefGoogle Scholar
  27. 27.
    B. J. McNelis, J. T. Starr, H. Dang, J. Heterocycl. Chem., 1998, 35, 1509.CrossRefGoogle Scholar
  28. 28.
    N. Choony, A. Dadabhoy, P. G. Sammes, J. Chem. Soc., Perkin Trans. 1, 1998, 2017.Google Scholar
  29. 29.
    I. M. Mándity, T. A. Martinek, F. Darvas, F. Fülöp, Tetrahedron Lett., 2009, 50, 4372.CrossRefGoogle Scholar
  30. 30.
    S. Chandrasekhara, B. V. D. Vijaykumara, B. M. Chandraa, Ch. R. Reddya, P. Naresh, Tetrahedron Lett., 2011, 52, 3865.CrossRefGoogle Scholar
  31. 31.
    K. Paulvannan, J. W. Jacobs, Tetrahedron, 1999, 55, 7433.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • V. P. Zaytsev
    • 1
    • 2
    Email author
  • F. I. Zubkov
    • 1
  • D. F. Mertsalov
    • 1
  • D. N. Orlova
    • 1
  • E. A. Sorokina
    • 1
  • E. V. Nikitina
    • 1
  • A. V. Varlamov
    • 1
  1. 1.Deparment of Organic ChemistryPeople’s Friendship University of RussiaMoscowRussian Federation
  2. 2.Shared Research and Educational Center of Physico-Chemical Studies of New Materials, Substances, and Catalytic Systems”MoscowRussian Federation

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