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Volumn , Issue 14, 2002, Pages 2057-2063

β-tosylethylhydroxylamine: Preparation and use as a hydroxylamine equivalent in amidyl radical-olefin cyclizations

Author keywords

Cyclizations; Lactams; Protecting groups; Radical reactions

Indexed keywords

CYCLIZATIONS;

EID: 0036398490     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (18)

References (32)
  • 1
    • 15044342910 scopus 로고    scopus 로고
    • For general reviews of nitrogen radical-olefin cyclizations see: (a) Esker, J. L.; Newcomb, M. Adv. Heterocycl. Chem. 1993, 58, 1. (b) Zard, S. Z. Synlett 1996, 1148. (c) Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543.
    • (1993) Adv. Heterocycl. Chem. , vol.58 , pp. 1
    • Esker, J.L.1    Newcomb, M.2
  • 2
    • 15044342910 scopus 로고    scopus 로고
    • For general reviews of nitrogen radical-olefin cyclizations see: (a) Esker, J. L.; Newcomb, M. Adv. Heterocycl. Chem. 1993, 58, 1. (b) Zard, S. Z. Synlett 1996, 1148. (c) Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543.
    • (1996) Synlett , vol.1148
    • Zard, S.Z.1
  • 3
    • 0030666083 scopus 로고    scopus 로고
    • For general reviews of nitrogen radical-olefin cyclizations see: (a) Esker, J. L.; Newcomb, M. Adv. Heterocycl. Chem. 1993, 58, 1. (b) Zard, S. Z. Synlett 1996, 1148. (c) Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543.
    • (1997) Tetrahedron , vol.53 , pp. 17543
    • Fallis, A.G.1    Brinza, I.M.2
  • 4
    • 0032485220 scopus 로고    scopus 로고
    • For some recent reports of the generation of amidyl radicals from hydroxamic acid derivatives see: (a) Clark, A. J.; Peacock, J. L. Tetrahedron Lett. 1998, 39, 1265. (b) Clark, A. J.; Filik, R. P.; Peacock, J. L.; Thomas, G. H. Synlett 1999, 441. (c) Clark, A. J.; Deeth, R. J.; Samuel, C. J.; Wongtap, H. Synlett 1999, 444.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 1265
    • Clark, A.J.1    Peacock, J.L.2
  • 5
    • 0032485220 scopus 로고    scopus 로고
    • For some recent reports of the generation of amidyl radicals from hydroxamic acid derivatives see: (a) Clark, A. J.; Peacock, J. L. Tetrahedron Lett. 1998, 39, 1265. (b) Clark, A. J.; Filik, R. P.; Peacock, J. L.; Thomas, G. H. Synlett 1999, 441. (c) Clark, A. J.; Deeth, R. J.; Samuel, C. J.; Wongtap, H. Synlett 1999, 444.
    • (1999) Synlett , vol.441
    • Clark, A.J.1    Filik, R.P.2    Peacock, J.L.3    Thomas, G.H.4
  • 6
    • 0032485220 scopus 로고    scopus 로고
    • For some recent reports of the generation of amidyl radicals from hydroxamic acid derivatives see: (a) Clark, A. J.; Peacock, J. L. Tetrahedron Lett. 1998, 39, 1265. (b) Clark, A. J.; Filik, R. P.; Peacock, J. L.; Thomas, G. H. Synlett 1999, 441. (c) Clark, A. J.; Deeth, R. J.; Samuel, C. J.; Wongtap, H. Synlett 1999, 444.
    • (1999) Synlett , vol.444
    • Clark, A.J.1    Deeth, R.J.2    Samuel, C.J.3    Wongtap, H.4
  • 19
    • 2142779526 scopus 로고    scopus 로고
    • note
    • We have made a few attempts to effect such a cyclization but without success.
  • 22
    • 0002877807 scopus 로고
    • For examples of TSE protection of nitrogen functionality in various heteroaromatics see: (a) Faubl, H. Tetrahedron Lett. 1979, 491. (b) Gonzalez, C.; Greenhouse, R.; Tallabs, R.; Muchowski, J. M. Can. J. Chem. 1983, 61, 1697. (c) Rao, A. K. S. B.; Rao, C. G.; Singh, B. B. Synth. Commun. 1994, 24, 341. (d) Bashford, K. E.; Cooper, A. L.; Kane, P. D.; Moody, C. J. Tetrahedron Lett. 2002, 43, 135.
    • (1979) Tetrahedron Lett. , pp. 491
    • Faubl, H.1
  • 23
    • 0000852293 scopus 로고
    • For examples of TSE protection of nitrogen functionality in various heteroaromatics see: (a) Faubl, H. Tetrahedron Lett. 1979, 491. (b) Gonzalez, C.; Greenhouse, R.; Tallabs, R.; Muchowski, J. M. Can. J. Chem. 1983, 61, 1697. (c) Rao, A. K. S. B.; Rao, C. G.; Singh, B. B. Synth. Commun. 1994, 24, 341. (d) Bashford, K. E.; Cooper, A. L.; Kane, P. D.; Moody, C. J. Tetrahedron Lett. 2002, 43, 135.
    • (1983) Can. J. Chem. , vol.61 , pp. 1697
    • Gonzalez, C.1    Greenhouse, R.2    Tallabs, R.3    Muchowski, J.M.4
  • 24
    • 0028265772 scopus 로고
    • For examples of TSE protection of nitrogen functionality in various heteroaromatics see: (a) Faubl, H. Tetrahedron Lett. 1979, 491. (b) Gonzalez, C.; Greenhouse, R.; Tallabs, R.; Muchowski, J. M. Can. J. Chem. 1983, 61, 1697. (c) Rao, A. K. S. B.; Rao, C. G.; Singh, B. B. Synth. Commun. 1994, 24, 341. (d) Bashford, K. E.; Cooper, A. L.; Kane, P. D.; Moody, C. J. Tetrahedron Lett. 2002, 43, 135.
    • (1994) Synth. Commun. , vol.24 , pp. 341
    • Rao, A.K.S.B.1    Rao, C.G.2    Singh, B.B.3
  • 25
    • 0036134118 scopus 로고    scopus 로고
    • For examples of TSE protection of nitrogen functionality in various heteroaromatics see: (a) Faubl, H. Tetrahedron Lett. 1979, 491. (b) Gonzalez, C.; Greenhouse, R.; Tallabs, R.; Muchowski, J. M. Can. J. Chem. 1983, 61, 1697. (c) Rao, A. K. S. B.; Rao, C. G.; Singh, B. B. Synth. Commun. 1994, 24, 341. (d) Bashford, K. E.; Cooper, A. L.; Kane, P. D.; Moody, C. J. Tetrahedron Lett. 2002, 43, 135.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 135
    • Bashford, K.E.1    Cooper, A.L.2    Kane, P.D.3    Moody, C.J.4
  • 26
    • 2142684848 scopus 로고    scopus 로고
    • note
    • 11
  • 29
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    • and references cited
    • This reaction might involve nucleophilic addition to an intermediate vinylnitroso compound: Gilchrist, T. L. Chem. Soc. Rev. 1983, 11, 53; and references cited.
    • (1983) Chem. Soc. Rev. , vol.11 , pp. 53
    • Gilchrist, T.L.1


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