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Intramolecular Sulfamylation Reaction of N-(1H-indol-3-yl)ethylsulfamides: Synthesis of 2,3,4,9-Tetrahydro-1,2-thiazino[5,6-b]indole 1,1-Dioxides

  • Lee, Ji-Sun (Department of Chemistry, Wonkwang University) ;
  • Lee, Dong-Geol (Department of Chemistry, Wonkwang University) ;
  • Park, Dong-Seub (Department of Chemistry, Wonkwang University) ;
  • Kim, Sun-Hee (Department of Chemistry, Wonkwang University) ;
  • Yoon, Han-Sik (School of Medical Radiation, Wonkwang Helth Science College) ;
  • Lee, Chai-Ho (Department of Chemistry, Wonkwang University)
  • Published : 2003.09.20

Abstract

Keywords

References

  1. Esteve, C.; Vidal, B. Tetrahedron Lett. 2002, 43, 1019. https://doi.org/10.1016/S0040-4039(01)02327-9
  2. Xiao, Z.; Timberlake, J. W. J. Heterocyclic Chem. 2000, 37, 773. https://doi.org/10.1002/jhet.5570370418
  3. Martinez, A.; Gil, C.; Prez, C.; Caastro, A.; Prieto, C.; Otero,J.; Andrei, G.; Snoek, R.; Balzarini, J.; Clercp, E. D. J. Med.Chem. 2000, 43, 3267 https://doi.org/10.1021/jm000118q
  4. Kuang, R.; Venkataraman, R.; Ruan,S.; Groutas, W. C. Bioorg. Med. Chem. Lett. 1998, 8, 539. https://doi.org/10.1016/S0960-894X(98)00067-5
  5. Lee, C.-H.; Kohn, H. J. Pharm. Sci. 1990, 70, 716.
  6. Lee, C.-H.;Korp, J. D.; Kohn, H. J. Org. Chem. 1989, 54, 3077. https://doi.org/10.1021/jo00274a023
  7. Gazieva, G. A.; Kravchenko, A. N.; Lebedev, O. V. RussianChem. Rev. 2000, 69(3), 221. https://doi.org/10.1070/RC2000v069n03ABEH000562
  8. Aran, V. J.; Goya, P.; Ochoa, C.Advances in Heterocyclic Chem. 1988, 44, 81. https://doi.org/10.1016/S0065-2725(08)60262-7
  9. McDermott, S.D.; Spillane, W. J. Org. Pre. & Proc. Int. 1984, 16(1), 49. https://doi.org/10.1080/00304948409356167
  10. McDermott, S. D.; Spillane, W. J. Synthesis 1983, 191.
  11. Paquin, A. M. Angew. Chem. 1948, 60, 316.
  12. Scott, F. L.; Schaumann, C. W.; King, J. P. J. Org. Chem.Commun. 1961, 26, 985. https://doi.org/10.1021/jo01062a072
  13. Kirsanov, A. V. J. Gen. Chem. 1952,22, 233.
  14. Lee, C. S.; Kim, S. H.; Lee, C.-H. J. Korean Chem. Soc. 1997, 41,677.
  15. Ohme, R.; Schmits, C. Angew. Chem. Int. Ed. Engl. 1965,4, 433.
  16. Breining, T.; Cimpoia, A. R.; Mansour, T. S.; Cammack, N.;Hopewell, P.; Ashman, C. Heterocycles 1995, 41, 87. https://doi.org/10.3987/COM-94-6887
  17. Jadhav,P. K.; Woerner, F. J. Tetrahedron Lett. 1995, 36, 6383. https://doi.org/10.1016/0040-4039(95)01319-D
  18. Castro,A.; Martinez, A. J. Chem. Soc., Perkin Trans. 1994, 2, 1561.
  19. Groutas, W. C.; Kuang, R.; Venkataraman, R. Biochem. Biophys.Res. Commun. 1994, 198, 341. https://doi.org/10.1006/bbrc.1994.1048
  20. Schwenker, G.; Guo, H. Arch.Pharm. 1993, 326, 45. https://doi.org/10.1002/ardp.19933260110
  21. Abd El Latif, F. M. Asian J. Chem.1993, 5, 184.
  22. Faleschini, G.; Nachbaur, E.; Belaj, F.Phosphorus Sulfur Silicon Relat. Elem. 1992, 65, 147. https://doi.org/10.1080/10426509208055340
  23. Alberola, A.; Andres, J. M.; Gonwalez, A.; Pedrosa, R.; Vicente,M. Synthesis 1991, 355.
  24. Esser, T.; Karu, A. E.; Toia, R. F.; Casida, J. E. Chem. Res. Toxicol. 1991, 4, 162. https://doi.org/10.1021/tx00020a007
  25. Alkorta, I.;Goya, P.; Paez, A. J. Heteracycles 1991, 32, 279. https://doi.org/10.3987/COM-90-5633
  26. Haake, M.;Schummelfelder, B. Synthesis 1991, 753.
  27. Lee, C.-H.; Kohn, H.J. Org. Chem. 1990, 55, 6098. https://doi.org/10.1021/jo00312a013
  28. Lee, C.-H.; Kohn, H. J.Heterocycl. Chem. 1990, 27, 2107. https://doi.org/10.1002/jhet.5570270747
  29. Goyal, R. N.; Bhargava, S.Curr. Sci. 1989, 58, 287.
  30. Alkorta, I.; Aran, V. J.; Davila, E.;Ruiz, J. R.; Stud, M. Liebigs Ann. Chem. 1989, 1135.
  31. Lee, C.-H.; Kohn, H. Heterocycles 1988, 27, 2581. https://doi.org/10.3987/COM-88-4618
  32. Aran, V. J.; Goya,P.; Ochoa, C. Adv. Heterocycl. Chem. 1988, 44, 81. https://doi.org/10.1016/S0065-2725(08)60262-7
  33. Span, P.547, 443; Chem. Abstr. 1988, 108, 6031.
  34. Alkorta, I.; Aran, V.J.; Bielsa, A. G.; Stud, M. J. Chem. Soc., Perkin Trans. 1989,1135.
  35. Aran, V. J.; Ruiz, J. R.; Davila, E.; Alkorta, I.; Stud, M.Liebigs Ann. Chem. 1988, 337.
  36. Dusemund, J.; Schurreit, T.Arch. Pharm. 1987, 320, 534. https://doi.org/10.1002/ardp.19873200610
  37. Dusemund, J.; Schurreit, T.Arch. Pharm. 1986, 319, 826. https://doi.org/10.1002/ardp.19863190909
  38. McDermott, S. D.; Spillane, W.J. Org. Prep. Proc. Int. 1984, 16, 49. https://doi.org/10.1080/00304948409356167
  39. Elguero, J.; Ochoa, C.;Stud, M.; Esteban-Calderon, C.; Martinez-Ripoll, M.; Iayet, J. P.;Vertut, M. C. J. Org. Chem. 1982, 47, 536. https://doi.org/10.1021/jo00342a033
  40. Petersen, H.Synthesis 1973, 243.
  41. Lawson, A.; Tinkler, R. B. Chem. Rev. 1970, 70, 593. https://doi.org/10.1021/cr60267a004
  42. Muller, G. W.; DuBois, G. E. J. Org. Chem. 1989, 54, 4471. https://doi.org/10.1021/jo00279a044
  43. Lee, J. S.; Yang, I. D.; Kim, S. H.; An, S. I.; Lee, C.-H. Bull.Korean Chem. Soc. 2003, 24(1), 129. https://doi.org/10.5012/bkcs.2003.24.1.129
  44. Lee, J. S.; Lee, C.-H.Bull. Korean Chem. Soc. 2002, 23(1), 167. https://doi.org/10.5012/bkcs.2002.23.1.167
  45. Lee, J. S.; Lee, C.H. J. Korean Chem. Soc. 2001, 45, 92.
  46. Kong, Y. J.; Kim, S. H.;Lee, C.-H. J. Korean Chem. Soc. 1999, 43, 131.
  47. Appel, R.; Berger, G. Chem. Ber. 1958, 91, 1339. https://doi.org/10.1002/cber.19580910633
  48. Graf, R. Chem. Ber. 1959, 92, 509. https://doi.org/10.1002/cber.19590920237
  49. CIBA Ltd. Belgium Patent 640,160,May 19, 1964
  50. CIBA Ltd. Chem. Abstr. 1950, 62, 16134e.
  51. Xiac, Z.; Timberlake, J. W. J. Heterocycl. Chem. 2000, 37,773. https://doi.org/10.1002/jhet.5570370418
  52. Dewynter, G.; Aouf, N.; Criton, M.; Montero, J. L.Tetrahedron 1993, 49(1), 65. https://doi.org/10.1016/S0040-4020(01)80506-8
  53. Sheldrick, G. M.; Kruger, C. Crystallographic Computing 3;Oxford University Press: London, 1985; pp 175-189.
  54. Sheldrick, G. M.; Flack, H. D.; Parkanyi, L.; Simon, K.Crystallographic Computing 6; Oxford University Press: London,1993; pp 111-189.

Cited by

  1. Intramolecular Sulfamylation Reaction of N-(1H-Indol-3-yl)ethylsulfamides: Synthesis of 2,3,4,9-Tetrahydro-1,2-thiazino[5,6-b]indole 1,1-Dioxides. vol.35, pp.7, 2003, https://doi.org/10.1002/chin.200407146