Synthesis, structure, and transformations of N-(alkyl-, benzyl-, arylsulfonyl)-N-(oxiran-2-ylmethyl)bicyclo[2.2.1]hept-5-en-exo-2-ylmethanamines

  • L. I. Kas’yan
  • V. A. Pal’chikov
  • S. A. Prid’ma
  • A. V. Turov
  • A. O. Kas’yan
  • A. V. Mazepa
  • V. E. Rybalko
Article

Abstract

Reactions of N-(alkyl-, benzyl-, arylsulfonyl)bicyclo[2.2.1]hept-5-en-exo-2-ylmethanamines with 2-(chloromethyl)oxirane in the presence of tetramethylammonium iodide gave a number of cage-like N-(oxiran-2-ylmethyl)sulfonamides, as well as N-(exo-5,6-epoxybicyclo[2.2.1]heptan-exo-2-ylmethyl)-4-nitro-N-(oxiran-2-ylmethyl)benzenesulfonamide. The latter was also synthesized by oxidation of oxiran-2-ylmethyl norbornene derivative with peroxy acids. Opening of the epoxide ring in N-(oxiran-2-ylmethyl) sulfonamides in reaction with benzylamine followed the Krasuskii rule, and the aminolysis of N-(exo-5,6-epoxybicyclo[2.2.1]-heptan-exo-2-ylmethyl)-4-nitro-N-(oxiran-2-ylmethyl)benzenesulfonamide chemoselectively occurred at the side-chain epoxy group.

Keywords

Oxirane Oily Substance Benzenesulfonamide Phthalic Anhydride Oxirane Ring 

References

  1. 1.
    Makarov, V.A., Kudrin, A.N., Chernykh, V.P., and Drogovoz, S.M., Farmakoterapiya sul’fanilamidnymi i sul’famidnymi preparatami (Pharmacotherapy Using Sulfanilamide and Sulfonamide Drugs), Kiev: Zdorov’e, 1991; Vizgert, R.V. and Mitchenko, E.S., Sintez i reaktsionnaya sposobnost’ proizvodnykh sul’fokislot (Synthesis and Reactivity of Sulfonic Acid Derivatives), Kiev: Naukova Dumka, 1992; Kas’yan, L.I., Kas’yan, A.O., Okovityi, S.I., and Tarabara, I.N., Aminy s karkasnymi fragmentami i ikh proizvodnye (Cage-Like Amines and Their Derivatives). Dnepropetrovsk: Dnepropetr. Univ., 2009; Mashkovskii, M.D., Lekarstvennye sredstva (Medicines), Moscow: Novaya Volna, 2002, 14th ed., vols. 1, 2.Google Scholar
  2. 2.
    Krieger, H., Arz.-Forsch., 1968, vol. 18, p. 487.Google Scholar
  3. 3.
    Ohtani, M., Narisada, M., Watanabe, F., Uchida, A.K., Arita, H., Doteuchi, M., Yeda, M., Hanasaki, K., Kakushi, H., Ohtani, K., Hara, S., and Nakajima, M., J. Pharmacobio-Dyn., 1989, vol. 12, p. 140; Ref. Zh., Khim., 1989, no. 24 O 277; Narisada, M., Ohtani, M., Watanabe, F., Hagishita, S., Seno, K., Kamata, S., Haga, N., Tsuri, T., Tsushima, T., and Kawada, K., US Patent no. 4 861 913, 1989; Ref. Zh., Khim., 1990, no. 22 O 132 P; Chem. Abstr., 1989, vol. 108, no. 111 866 e; Watanabe, F., Narisada, M., Ohtani, M., Hagishita, S., Tsuri, T., Seno, K., Tsushima, T., Kamata, S., Kawada, K., and Haga, N., EP Patent no. 0 226 346, 1987; Chem. Abstr., 1988, vol. 108, no. 111 868; Narisada, M., Ohtani, M., Hagishita, Y., Seno, K., and Kishi, M., JPN Patent Appl. no. 63–284 158, 1988; Chem. Abstr., 1990, vol. 112, no. 35 549; Narisada, M., Watanabe, F., Ohtani, M., and Kawata, K., EU Patent no. 0 373 951, 1990; Chem. Abstr., 1991, vol. 114, p. 6146; Narisada, M., Ohtani, M., Watanabe, F., Hagishita, Y., Seno, K., Kamata, S., Haga, N., Tsuri, T., Tsushima, T., and Kawada, K., JPN Patent Appl. no. 63-139 161, 1988; Ref. Zh., Khim., 1990, no. 11 O 40 P; Narisada, M., Ohtani, M., Watanabe, F., and Matsuura, K., JPN Patent Appl. no. 22–18 660, 1990; Ref. Zh., Khim., 1992, no. 15 O 216 P.Google Scholar
  4. 4.
    Katama, S., Nobuhiro, H., Tsuri, T., Uchida, K., Kakushi, H., and Hanasaki, K., J. Med. Chem., 1990, vol. 33, p. 229; Mais, D.E., Mohamadi, F., Dobi, G.P., Kurtz, W.L., Brune, K.A., Utterbick, B.G., Spees, M.M., and Jakubowski, J.A., Eur. J. Med. Chem., 1991, vol. 26, p. 821.CrossRefGoogle Scholar
  5. 5.
    Narisada, M., Ohtani, M., Watanabe, F., Uchida, K., Arita, H., Doteuchi, M., Manosaki, K., Kakushi, H., Ohtani, K., and Hara, S., J. Med. Chem., 1988, vol. 31, p. 1847.CrossRefGoogle Scholar
  6. 6.
    Martinelli, M.J., J.Org. Chem., 1990, vol. 55, p. 5065; Ohtani, M., Matsuura, T., Watanabe, F., and Narisada, M., J. Org. Chem., 1991, vol. 56, p. 2122; Furuta, K. and Hayashi, Sh., Miwa, Y., and Yamamoto, H., Tetrahedron Lett., 1987, vol. 28, p. 5841.CrossRefGoogle Scholar
  7. 7.
    Hamanaka, N., Seko, T., Miyazaki, I., Naka, M., Furuta, K., and Yamamoto, H., Tetrahedron Lett., 1989, vol. 30, p. 2399; Murata, M., Ikoma, S., and Achiwa, K., Chem. Pharm. Bull., 1990, vol. 38, p. 2329.CrossRefGoogle Scholar
  8. 8.
    Lieb, F., Oediger, H., Böshagen, H., Rosentreter, U., Niewöhner, U., Hoever, P., Perzborn, E., Seuter, F., and Fiedler, V.-B., FRG Patent Appl. no. 3 720 760, 1989; Ref. Zh., Khim., 1990, no. 2 O 80 P.Google Scholar
  9. 9.
    Zlenko, E.T., Kas’yan, A.O., Mamchur, V.I., Demchenko, E.M., Markov, V.I., and Tronenko, L.D., Ukrainian Patent no. 10 504A, 1996; Byull. Prom. Sobstv., 1996, no. 2; Kas’yan, L.I., Zlenko, O.T., Mamchur, V.I., Kas’yan, A.O., Gaponova, R.G., Demchenko, O.M., Tronenko, L.D., Volkova-Skachko, T.A., and Tarabara, I.M., Ukrainian Patent no. 46 836A, 2002; Byull. Prom. Sobstv., 2002, no. 6; Zlenko, O.T., Kas’yan, L.I., Danilenko, G.I., Mamchur, V.I., Kas’yan, A.O., Podpletnya, O.A., Budchenko, S.I., Krasnovs’ka, O.Yu., and Guzhova, S.V., Ukrainian Patent no. 46 830A, 2002; Byull. Prom. Sobstv., 2002, no. 6; Zlenko, E.T., Mamchur, V.I., Kas’yan, L.I., Kas’yan, A.O., and Karpenko, D.V., Zaporozh. Med. Zh., 2004, vol. 1, no. 22, p. 48; Kas’yan, L.I., Zlenko, E.T., Mamchur, V.I., Kas’yan, A.O., and Tarabara, I.N., Farm. Zh., 2002, no. 2, p. 59; Kas’yan, L.I., Zlenko, E.T., Turov, A.V., Prid’ma, S.A., and Kas’yan, A.O., Zh. Org. Farm. Khim., 2008, vol. 6, no. 3, p. 76; Zlenko, E.T., Kas’yan, L.I., Mamchur, V.I., Kas’yan, A.O., Prid’ma, S.A., Pal’chikov, V.A., and Karat, L.D., Zh. Org. Farm. Khim., 2009, vol. 7, no. 1, p. 64.Google Scholar
  10. 10.
    Alder, K., Heimbach, K., and Reubke, R., Chem. Ber., 1958, vol. 91, p. 1516.CrossRefGoogle Scholar
  11. 11.
    Markov, V.I., Kas’yan, A.O., and Selyutin, O.B., Ukr. Khim. Zh., 1994, vol. 60, p. 575; Kasyan, L.I., Tarabara, I.N., Kasyan, A.O., Okovytyy, S.I., Tokar, A.V., Shishkina, S.V., and Shishkin, O.V., Tetrahedron, 2007, vol. 63, p. 1790; Kas’yan, A.O., Maletina, I.I., Yagupol’skii, L.M., Markov, V.I., and Kas’yan, L.I., Russ. J. Org. Chem., 1995, vol. 31, p. 320; Kas’yan, L.I., Kas’yan, A.O., Gorb, L.G., and Klebanov, B.M., Russ. J. Org. Chem., 1995, vol. 31, p. 626.Google Scholar
  12. 12.
    Zlenko, E.T., Kas’yan, A.O., Tarabara, I.N., Efimenko, V.V., and Kas’yan, L.I., Vopr. Khim. Khim. Tekhnol., 2004, no. 5, p. 31.Google Scholar
  13. 13.
    Kas’yan, L.I., Usp. Khim., 1998, vol. 67, p. 299; Kas’yan, L.I., Seferova, M.F., and Okovityi, S.I., Alitsiklicheskie epoksidnye soedineniya. Metody Sinteza (Alicyclic Epoxide Compounds. Methods of Synthesis), Dnepropetrovsk: Dnepropetr. Gos. Univ., 1996; Kasyan, L.I., Sereda, S.V., Potekhin, K.A., and Kasyan, A.O., Heteroatom Chem., 1997, vol. 8, p. 177.Google Scholar
  14. 14.
    Kas’yan, A.O., Isaev, A.K., and Kas’yan, L.I., Russ. J. Org. Chem., 2002, vol. 38, p. 553.CrossRefGoogle Scholar
  15. 15.
    Rakhmankulov, D.L., Kimsanov, B.Kh., Loktionov, N.A., Dmitriev, Yu.K., and Chanyshev, R.R., Epikhlorgidrin. Metody polucheniya, fizicheskie i khimicheskie svoistva, tekhnologii proizvodstva (Epichlorohydrin. Methods of Preparation, Physical and Chemical Properties, and Technologies of Large-Scale Synthesis), Moscow: Khimiya, 2003.Google Scholar
  16. 16.
    Karat, L.D. and Strel’tsov, V.I., Zh. Prikl. Khim., 1993, vol. 66, p. 1069; Karat, L.D., Strel’tsov, V.I., Kulik, T.A., and Pilipenko, T.I., Ukr. Khim. Zh., 1994, vol. 60, p. 303; Karat, L.D., Strel’tsov, V.I., and Karpov, O.N., Kinet. Katal., 1993, vol. 34, p. 667; Karat, L.D., Strel’tsov, V.I., and Karpov, O.N., Zh. Org. Khim., 1992, vol. 28, p. 2459.Google Scholar
  17. 17.
    Nakanishi, K., Infrared Absorption Spectroscopy. Practical, San Francisco: Holden-Day, 1962; Bellamy, L.J., Advances in Infra-red Group Frequencies, London: Methuen, 1966.Google Scholar
  18. 18.
    Zefirov, N.S. and Sokolov, V.I., Usp. Khim., 1967, vol. 36, p. 243.Google Scholar
  19. 19.
    Nechitailo, L.G., Reznikova, M.Z., Shologon, I.M., and Pakter, M.K., IK spektroskopiya epoksidnykh smol (IR Spectroscopy of Epoxy Resins), Moscow: NIITEKhIM, 1988.Google Scholar
  20. 20.
    Claridge, T.D.W., High-Resolution NMR Techniques in Organic Chemistry. Oxford: Pergamon, 1999.Google Scholar
  21. 21.
    Tori, K., Kitahonoki, K., Tanida, H., and Tsuji, T., Tetrahedron Lett., 1964, vol. 5, p. 559; Shashkov, L.Yu., Cherepanova, E.G., Kas’yan, L.I., Gnedenkov, L.Yu., and Bombushkar’, M.V., Izv. Akad. Nauk SSSR. Ser. Khim., 1980, p. 564; Zefirov, N.S., Kasyan, L.I., Gnedenkov, L.Yu., Shashkov, A.S., and Cherepanova, E.G., Tetrahedron Lett., 1979, vol. 20, p. 949.CrossRefGoogle Scholar
  22. 22.
    Pal’chikov, V.A. and Kas’yan, L.I., Visn. Dnipropetr. Univ., Khim., 2008, no. 14, p. 7; Kas’yan, L.I., Pal’chikov, V.A., Turov, A.V., Prid’ma, S.A., and Tokar’, A.V., Russ. J. Org. Chem., 2009, vol. 45, p. 1007.Google Scholar
  23. 23.
    Kas’yan, L.I., Kas’yan, A.O., Okovityi, S.I., and Tarabara, I.N., Alitsiklicheskie epoksidnye soedineniya. Reaktsionnaya sposobnost’ (Alicyclic Epoxy Compounds. Reactivity). Dnepropetrovsk: Dnepropetr. Univ., 2003; Kas’yan, L.I. and Pal’chikov, V.A., Russ. J. Org. Chem., 2010, vol. 46, p. 1.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2011

Authors and Affiliations

  • L. I. Kas’yan
    • 1
  • V. A. Pal’chikov
    • 1
  • S. A. Prid’ma
    • 1
  • A. V. Turov
    • 2
  • A. O. Kas’yan
    • 3
  • A. V. Mazepa
    • 4
  • V. E. Rybalko
    • 1
  1. 1.Oles’ Gonchar Dnepropetrovsk National UniversityDnepropetrovskUkraine
  2. 2.Shevchenko Kiev National UniversityKievUkraine
  3. 3.ProBioGen A.G.BerlinGermany
  4. 4.Bogatskii Physicochemical InstituteNational Academy of Sciences of UkraineOdessaUkraine

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