Russian Journal of Organic Chemistry

, Volume 38, Issue 4, pp 553–563 | Cite as

New N-(Arylsulfonyl)-5-aminomethylbicyclo[2.2.1]hept-2-enes. Synthesis, 1H and 13C NMR Spectra, and Chemical Reactions

  • A. O. Kas'yan
  • A. K. Isaev
  • L. I. Kas'yan


A synthesis of new N-(arylsulfonyl)-5-aminomethylbicyclo[2.2.1]hept-2-enes obtained by reaction of stereoisomeric exo- and endo-5-aminomethylbicyclo[2.2.1]hept-2-enes with arylsulfonyl chlorides is described. With the use of the data of 1H and 13C NMR spectra, including those of two-dimensional spectra recorded in COSY and NOESY mode, the contribution of stereochemical features of sulfonamides into the spectra structure of endo- and exo-isomers was evaluated. Applying various methods of the phase-transfer catalysis alkylation and acylation of the stereoisomeric arylsulfonamides containing a norbornene fragment was carried out. The reactions of alkylated stereoisomeric sulfonamides, N-(benzyl)-N-(3,4-dichlorophenylsulfonyl)-5-aminomethylbicyclo[2.2.1]hept-2-enes, with peroxyphthalic acid provide epoxides; the orientation of substituents in the cage norbornene fragment does not affect the direction of the process. The structure of the products obtained by sulfonamides transformations was confirmed by IR, 1H and 13C NMR spectra.


Cage Catalysis Benzyl Epoxide Alkylation 
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  1. 1.
    Makarov, V.A., Kudrin, A.N., Chernykh, V.P., and Drogovoz, S.M., Farmakoterapiya su' fanilamidnymi i sul'famidnymi preparatami (Pharmacotherapy with sulfonamide and sulfamide preparations), Kiev: Zdorov'e, 1991, 190 p.; Vizgert, R.V. and Mitchenko, E.S., Sintez i reaktsionnaya sposobnost'proizvodnykh sul'fokislot (Synthesis and reactivity of sulfonic acids derivatives), Kiev: Naukovadumka, 1992, 273 p.Google Scholar
  2. 2.
    Krieger, H., Arzneimittel-Forschung, 1968, vol. 18, pp. 478-493.Google Scholar
  3. 3.
    German Patent 3720760, 1989. Ref. Zh. Khim., 1990, 2O80.Google Scholar
  4. 4.
    Krieger, H., Arzneimittel-Forschung, 1968, vol. 18, pp. 129-134, 324-330.Google Scholar
  5. 5.
    Markov, V.I., Kas' yan, A.O., Tudvaseva, S.P., and Okovityi, S.I., Ukr. Khim. Zh., 1993, vol. 59, no. 6, pp. 575-581; Markov V.I., Kas'yan, A.O., Selyutin, O.B., Ukr. Khim. Zh., 1994, vol. 60, no. 8, pp. 650-654.Google Scholar
  6. 6.
    Kas'yan, A.O., Maletina, I.I., Yagupol'skii, L.M., Markov, V.I., and Kas'yan, L.I., Zh. Org. Khim., 1995, vol. 31, no. 3, pp. 357-364.Google Scholar
  7. 7.
    Kas'yan, A.O., Kas'yan, L.I., Gorb, L.G., and Klebanov, B.M., Zh. Org. Khim., 1995, vol. 31, no. 5, pp. 678-688.Google Scholar
  8. 8.
    Kas'yan, L.I., Zlenko, H.T., Kas'yan, A.O., Krasnovski, O.Yu., and Gaponova, R. G., Abstracts of Papers, XIV International Symposium on Medicinal Chemistry, Maastricht, 1996, p. 308; Zlenko, H., Mamchur, V., and Kasyan, L., European Psychiatry, 1997, vol. 12, no. 2, p. 218; Zlenko, H., Kasyan, L., Mamchur, V., Kasyan, A., Podpletnjaja, H., Tarabara, I., and Krishchik, O., Fundamental and Clinical Pharmacology, 1999, vol. 13, no. 1, p. 377; Zlenko, H. Skotchko-Volkova, T., Mamchur, V., Demchenko, H., Kasyan, L., and Tarabara, I., Pathphysiology, 1998, vol. 5, no. 6, p. 27; Kasyan, L.I., Zlenko, H.T., Kasyan, A.O., and Tarabara, I.N., Abstracts of Papers, XV International Symposiumon Medicinal Chemistry, Edinburgh, 1998, p. 204.Google Scholar
  9. 9.
    Kas'yan, A.O., Krasnovskaya, O.Yu., Zlenko, E.T., Okovityi, S.I., and Kas'yan, L.I., Zh. Org. Khim., 1996, vol. 32, no. 8, pp. 1156-1164.Google Scholar
  10. 10.
    Narisada, M., Ohtani, M., Watanabe, F., Uchida, K., Arita, H., Poteuchi, M., Hanasaki, K., Kakuchi, H., Otahi, K., and Hara, S., J. Med. Chem., 1988, vol. 31, no. 9, pp. 1847-1854; Hamanaka, N., Seko, T., Miyazari, T., Naka, M., Furata, K., and Yamamoto, H., Tetrahedron Lett., 1989, vol. 30, no. 18, pp. 2399-2402; Murata, M., Ikoma, S., and Achiva, K., Chem. Pharm. Bull., 1990, vol. 38, no. 8, pp. 2329-2331; Kamata, S., Haga, N., Tsuri, T., Ushida, K., Kakuchi, H., Arita, H., and Hanasaki, K., J. Med. Chem., 1990, vol. 33, no. 1, pp. 229-239; Ohtani, M. and Narisada, M., J. Med. Chem., 1990, vol. 33, no. 3, pp. 1027-1031.Google Scholar
  11. 11.
    Kas'yan, L.I., Sereda, S.V., Potekhin, K.A., and Kas'yan, A.O., Heteroatom Chem., 1997, vol. 8, no. 2, pp. 177-184.Google Scholar
  12. 12.
    Kas'yan, L.I., Zlenko, O.T., Kas'yan, A.O., and Tarabara, I.M., Farmatsevtichnii Zhurn., 2001, no. 4, pp. 54-57.Google Scholar
  13. 13.
    Alder, K., Krieger, H., and Weiss, H., Chem. Ber., 1955, vol. 88, no. 1, pp. 144-145; Alder, K., Heimbach, K., and Reubke, R., Chem. Ber., 1958, vol. 91, no. 7, pp. 1516-1524.Google Scholar
  14. 14.
    Wilder, P. and Knight, D.B., J. Org. Chem., 1965, vol. 30, no. 9, pp. 3078-3081.Google Scholar
  15. 15.
    Nakanisi, K., Infrakrasnye spektry organicheskikh molekul (IR Spectra of Organic Molecules), Moscow: Mir, 1965.Google Scholar
  16. 16.
    Shashkov, A.S., Cherepanova, E.G., Kas'yan, L.I., Gnedenkov, L.Yu., and Bombushkar, M.F., Izv. Akad. Nauk SSSR, Ser. Khim., 1980, no. 3, pp. 564-569.Google Scholar
  17. 17.
    Kas'yan, A.O., Tarabara, I.N., Zlenko, E.T., Okovityi, S.I., and Kas'yan, L.I., Zh. Org. Khim., 1999, vol. 35, no. 7, pp. 1042-1155.Google Scholar
  18. 18.
    Kas'yan, L.I., Seljutin, O.B., Krasnovskaja, O. Yu., and Kas'yan, A.O., Abstr. Book of Colloquium Spectroscopicum Internationale XXIX, Leipzig, 1995, p. 421; Kas'yan, L.I., Tarabara, I.N., Krishchik, O.V., and Kasyan, A.O., Spectroscopy of Biological Molecules: Modern Trends, Carmona, S., Navarro, R., and Hernanz, A., Eds., Madrid: Annex, 1997, pp. 121-122.Google Scholar
  19. 19.
    Kas'yan, A.O., Zlenko, E.T., Tarabara, I.N., Markov, V.I., and Kas'yan, L.I., Voprosy Khim. i Khim. Tekhnologii, 1998, no. 4, pp. 7-10.Google Scholar
  20. 20.
    Kas'yan, L.I., Okovity, S.I., and Kas'yan, A.O., Heteroatom. Chem., 1997, vol. 8, no. 2, pp. 185-190.Google Scholar

Copyright information

© MAIK “Nauka/Interperiodica” 2002

Authors and Affiliations

  • A. O. Kas'yan
    • 1
  • A. K. Isaev
    • 2
  • L. I. Kas'yan
    • 2
  1. 1.Rein-Westfalen Technische UniversitaetAachen
  2. 2.Dnepropetrovsk State UniversityDnepropetrovskUkraine

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