메뉴 건너뛰기




Volumn 62, Issue 10, 1997, Pages 3103-3108

Intramolecular homolytic substitution with amidyl radicals: A free-radical synthesis of ebselen and related analogues

Author keywords

[No Author keywords available]

Indexed keywords

EBSELEN; EBSELEN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0030973260     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970019t     Document Type: Article
Times cited : (70)

References (43)
  • 7
    • 0028801183 scopus 로고
    • Drugs Future 1995, 20, 1057.
    • (1995) Drugs Future , vol.20 , pp. 1057
  • 12
    • 8544255642 scopus 로고    scopus 로고
    • European Patent EP 44453
    • European Patent EP 44453.
  • 14
    • 0030583482 scopus 로고    scopus 로고
    • and references cited therein
    • Schiesser, C. H.; Wild, L. M. Tetrahedron 1996, 52, 13265 and references cited therein.
    • (1996) Tetrahedron , vol.52 , pp. 13265
    • Schiesser, C.H.1    Wild, L.M.2
  • 15
    • 8544250703 scopus 로고
    • Schiesser, C. H.; Sutej, K. J. Chem. Soc., Chem. Commun. 1992, 57. Schiesser, C. H.; Sutej. K. Tetrahedron Lett. 1992, 33, 5137. Lyons, J. E.; Schiesser, C. H.; Sutej, K. J. Org. Chem. 1993, 58, 5632. Benjamin, L. J.; Schiesser, C. H.; Sutej, K. Tetrahedron 1993, 49, 2557. Schiesser, C. H.; Fong, M. C.; Schiesser, C. H. Tetrahedron Lett. 1993, 34, 4347. Lucas, M. A.; Schiesser, C. H. J. Org. Chem. 1996, 61, 5754.
    • (1992) J. Chem. Soc., Chem. Commun. , vol.57
    • Schiesser, C.H.1    Sutej, K.2
  • 16
    • 0026657341 scopus 로고
    • Schiesser, C. H.; Sutej, K. J. Chem. Soc., Chem. Commun. 1992, 57. Schiesser, C. H.; Sutej. K. Tetrahedron Lett. 1992, 33, 5137. Lyons, J. E.; Schiesser, C. H.; Sutej, K. J. Org. Chem. 1993, 58, 5632. Benjamin, L. J.; Schiesser, C. H.; Sutej, K. Tetrahedron 1993, 49, 2557. Schiesser, C. H.; Fong, M. C.; Schiesser, C. H. Tetrahedron Lett. 1993, 34, 4347. Lucas, M. A.; Schiesser, C. H. J. Org. Chem. 1996, 61, 5754.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 5137
    • Schiesser, C.H.1    Sutej, K.2
  • 17
    • 0001189095 scopus 로고
    • Schiesser, C. H.; Sutej, K. J. Chem. Soc., Chem. Commun. 1992, 57. Schiesser, C. H.; Sutej. K. Tetrahedron Lett. 1992, 33, 5137. Lyons, J. E.; Schiesser, C. H.; Sutej, K. J. Org. Chem. 1993, 58, 5632. Benjamin, L. J.; Schiesser, C. H.; Sutej, K. Tetrahedron 1993, 49, 2557. Schiesser, C. H.; Fong, M. C.; Schiesser, C. H. Tetrahedron Lett. 1993, 34, 4347. Lucas, M. A.; Schiesser, C. H. J. Org. Chem. 1996, 61, 5754.
    • (1993) J. Org. Chem. , vol.58 , pp. 5632
    • Lyons, J.E.1    Schiesser, C.H.2    Sutej, K.3
  • 18
    • 0027522635 scopus 로고
    • Schiesser, C. H.; Sutej, K. J. Chem. Soc., Chem. Commun. 1992, 57. Schiesser, C. H.; Sutej. K. Tetrahedron Lett. 1992, 33, 5137. Lyons, J. E.; Schiesser, C. H.; Sutej, K. J. Org. Chem. 1993, 58, 5632. Benjamin, L. J.; Schiesser, C. H.; Sutej, K. Tetrahedron 1993, 49, 2557. Schiesser, C. H.; Fong, M. C.; Schiesser, C. H. Tetrahedron Lett. 1993, 34, 4347. Lucas, M. A.; Schiesser, C. H. J. Org. Chem. 1996, 61, 5754.
    • (1993) Tetrahedron , vol.49 , pp. 2557
    • Benjamin, L.J.1    Schiesser, C.H.2    Sutej, K.3
  • 19
    • 0027213151 scopus 로고
    • Schiesser, C. H.; Sutej, K. J. Chem. Soc., Chem. Commun. 1992, 57. Schiesser, C. H.; Sutej. K. Tetrahedron Lett. 1992, 33, 5137. Lyons, J. E.; Schiesser, C. H.; Sutej, K. J. Org. Chem. 1993, 58, 5632. Benjamin, L. J.; Schiesser, C. H.; Sutej, K. Tetrahedron 1993, 49, 2557. Schiesser, C. H.; Fong, M. C.; Schiesser, C. H. Tetrahedron Lett. 1993, 34, 4347. Lucas, M. A.; Schiesser, C. H. J. Org. Chem. 1996, 61, 5754.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 4347
    • Schiesser, C.H.1    Fong, M.C.2    Schiesser, C.H.3
  • 20
    • 0000950936 scopus 로고    scopus 로고
    • Schiesser, C. H.; Sutej, K. J. Chem. Soc., Chem. Commun. 1992, 57. Schiesser, C. H.; Sutej. K. Tetrahedron Lett. 1992, 33, 5137. Lyons, J. E.; Schiesser, C. H.; Sutej, K. J. Org. Chem. 1993, 58, 5632. Benjamin, L. J.; Schiesser, C. H.; Sutej, K. Tetrahedron 1993, 49, 2557. Schiesser, C. H.; Fong, M. C.; Schiesser, C. H. Tetrahedron Lett. 1993, 34, 4347. Lucas, M. A.; Schiesser, C. H. J. Org. Chem. 1996, 61, 5754.
    • (1996) J. Org. Chem. , vol.61 , pp. 5754
    • Lucas, M.A.1    Schiesser, C.H.2
  • 22
    • 37049047509 scopus 로고
    • Barton, D. H. R.; Beckwith, A. L. J.; Goosen, A. J. Chem. Soc. 1965, 181. Glover, S. A.; Goosen, A. J. Chem. Soc. Perkin Trans. 1 1974, 2353. Kuehne, M. E.; Horne, D. A. J. Org. Chem. 1975, 40, 1287. Mackiewicz, P.; Furstoss, R.; Waegell, B.; Cote, R.; Lessard, J. J. Org. Chem. 1978, 43, 3746. Glover, S. A.; Goosen, A. J. Chem. Soc., Perkin Trans. 1 1978, 653. Chow, Y. L.; Perry, R. A. Can. J. Chem. 1985, 63, 2203
    • (1965) J. Chem. Soc. , pp. 181
    • Barton, D.H.R.1    Beckwith, A.L.J.2    Goosen, A.3
  • 23
    • 37049130225 scopus 로고
    • Barton, D. H. R.; Beckwith, A. L. J.; Goosen, A. J. Chem. Soc. 1965, 181. Glover, S. A.; Goosen, A. J. Chem. Soc. Perkin Trans. 1 1974, 2353. Kuehne, M. E.; Horne, D. A. J. Org. Chem. 1975, 40, 1287. Mackiewicz, P.; Furstoss, R.; Waegell, B.; Cote, R.; Lessard, J. J. Org. Chem. 1978, 43, 3746. Glover, S. A.; Goosen, A. J. Chem. Soc., Perkin Trans. 1 1978, 653. Chow, Y. L.; Perry, R. A. Can. J. Chem. 1985, 63, 2203
    • (1974) J. Chem. Soc. Perkin Trans. 1 , pp. 2353
    • Glover, S.A.1    Goosen, A.2
  • 24
    • 0001685816 scopus 로고
    • Barton, D. H. R.; Beckwith, A. L. J.; Goosen, A. J. Chem. Soc. 1965, 181. Glover, S. A.; Goosen, A. J. Chem. Soc. Perkin Trans. 1 1974, 2353. Kuehne, M. E.; Horne, D. A. J. Org. Chem. 1975, 40, 1287. Mackiewicz, P.; Furstoss, R.; Waegell, B.; Cote, R.; Lessard, J. J. Org. Chem. 1978, 43, 3746. Glover, S. A.; Goosen, A. J. Chem. Soc., Perkin Trans. 1 1978, 653. Chow, Y. L.; Perry, R. A. Can. J. Chem. 1985, 63, 2203
    • (1975) J. Org. Chem. , vol.40 , pp. 1287
    • Kuehne, M.E.1    Horne, D.A.2
  • 25
    • 0000886776 scopus 로고
    • Barton, D. H. R.; Beckwith, A. L. J.; Goosen, A. J. Chem. Soc. 1965, 181. Glover, S. A.; Goosen, A. J. Chem. Soc. Perkin Trans. 1 1974, 2353. Kuehne, M. E.; Horne, D. A. J. Org. Chem. 1975, 40, 1287. Mackiewicz, P.; Furstoss, R.; Waegell, B.; Cote, R.; Lessard, J. J. Org. Chem. 1978, 43, 3746. Glover, S. A.; Goosen, A. J. Chem. Soc., Perkin Trans. 1 1978, 653. Chow, Y. L.; Perry, R. A. Can. J. Chem. 1985, 63, 2203
    • (1978) J. Org. Chem. , vol.43 , pp. 3746
    • Mackiewicz, P.1    Furstoss, R.2    Waegell, B.3    Cote, R.4    Lessard, J.5
  • 26
    • 37049101458 scopus 로고
    • Barton, D. H. R.; Beckwith, A. L. J.; Goosen, A. J. Chem. Soc. 1965, 181. Glover, S. A.; Goosen, A. J. Chem. Soc. Perkin Trans. 1 1974, 2353. Kuehne, M. E.; Horne, D. A. J. Org. Chem. 1975, 40, 1287. Mackiewicz, P.; Furstoss, R.; Waegell, B.; Cote, R.; Lessard, J. J. Org. Chem. 1978, 43, 3746. Glover, S. A.; Goosen, A. J. Chem. Soc., Perkin Trans. 1 1978, 653. Chow, Y. L.; Perry, R. A. Can. J. Chem. 1985, 63, 2203
    • (1978) J. Chem. Soc., Perkin Trans. 1 , pp. 653
    • Glover, S.A.1    Goosen, A.2
  • 27
    • 0000998688 scopus 로고
    • Barton, D. H. R.; Beckwith, A. L. J.; Goosen, A. J. Chem. Soc. 1965, 181. Glover, S. A.; Goosen, A. J. Chem. Soc. Perkin Trans. 1 1974, 2353. Kuehne, M. E.; Horne, D. A. J. Org. Chem. 1975, 40, 1287. Mackiewicz, P.; Furstoss, R.; Waegell, B.; Cote, R.; Lessard, J. J. Org. Chem. 1978, 43, 3746. Glover, S. A.; Goosen, A. J. Chem. Soc., Perkin Trans. 1 1978, 653. Chow, Y. L.; Perry, R. A. Can. J. Chem. 1985, 63, 2203
    • (1985) Can. J. Chem. , vol.63 , pp. 2203
    • Chow, Y.L.1    Perry, R.A.2
  • 34
    • 8544221237 scopus 로고    scopus 로고
    • note
    • The transformation of 13 into 1 can be achieved by the reaction of 13 with 1.5 equiv of benzoyl peroxide in benzene under reflux. In our hands, superior yields were always obtained by the stepwise transformation 13 → 15 → 1, especially in the preparation of ebselen (1: R = Ph) where solubility problems are encountered.
  • 36
    • 8544229273 scopus 로고    scopus 로고
    • note
    • A reviewer suggested that tert-butyl peroxide may be undergoing induced decomposition at 120 °C, thus acting as a more effective scavenger of methyl radicals at higher concentrations.
  • 37
    • 8544237884 scopus 로고    scopus 로고
    • note
    • TLC analysis indicated that the starting material was consumed after 16 h. Prolonged exposure to tert-butyl peroxide at 120 °C resulted in a significantly darker reaction mixture and diminished yields of ebselen (1, R = Ph).
  • 43
    • 8544272625 scopus 로고    scopus 로고
    • note
    • Heating concentrated tert-butyl peroxide at 120 °C is potentially hazardous and should never be attempted on a large scale. This experiment was carried our behind a protective (safety) shield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.