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Volumn 10, Issue 18, 2008, Pages 4009-4012

Stereoselective oxidative rearrangement of 2-aryl tryptamine derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; INDOLE DERIVATIVE; OXINDOLE; PYRROLE DERIVATIVE; TRYPTAMINE; TRYPTAMINE DERIVATIVE;

EID: 55949122492     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8015176     Document Type: Article
Times cited : (93)

References (38)
  • 7
    • 0005771880 scopus 로고    scopus 로고
    • For examples of aryl migration, see: (a) Witkop, B, Ek, A. J. Am. Chem. Soc. 1951, 73, 5664
    • For examples of aryl migration, see: (a) Witkop, B.; Ek, A. J. Am. Chem. Soc. 1951, 73, 5664.
  • 10
    • 0037326264 scopus 로고    scopus 로고
    • and references cited therein. For elegant examples, please see: a
    • For elegant examples, please see: (a) Williams, R. M.; Cox, R. J. Acc. Chem. Res. 2003, 36, 127, and references cited therein.
    • (2003) Acc. Chem. Res , vol.36 , pp. 127
    • Williams, R.M.1    Cox, R.J.2
  • 23
    • 61349161454 scopus 로고    scopus 로고
    • While control experiments revealed no product inhibition by either the indoxyl or the oxindole products, we prefer the use of stoichiometric quantities of scandium trifluoromethanesulfonate to accelerate the overall rate of conversion to the desired product compare entries 8 and 9, Table 1
    • While control experiments revealed no product inhibition by either the indoxyl or the oxindole products, we prefer the use of stoichiometric quantities of scandium trifluoromethanesulfonate to accelerate the overall rate of conversion to the desired product (compare entries 8 and 9, Table 1).
  • 24
    • 0026733301 scopus 로고
    • For an important observation with a dialkyl indoxyl, see: a
    • For an important observation with a dialkyl indoxyl, see: (a) Güller, R.; Borscheberg, H. Tetrahedron: Asymmetry 1992, 3, 1197.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 1197
    • Güller, R.1    Borscheberg, H.2
  • 25
    • 0028344381 scopus 로고    scopus 로고
    • 2) led to decomposition.
    • 2) led to decomposition.
  • 27
    • 0025324468 scopus 로고    scopus 로고
    • For 3-n-butyl-1,2-benzisothiazole-1,1-dioxide oxide, see: Davis, F. A.; Towson, J. C.; Vashi, D. B.; ThimmaReddy, R.; McCauley, J. P., Jr.; Harakal, M. E.; Gosciniak, D. J. J. Org. Chem. 1990, 55, 1254. Use of this reagent generally resulted in cleaner reaction mixtures than those observed with in situ generated DMDO.
    • For 3-n-butyl-1,2-benzisothiazole-1,1-dioxide oxide, see: Davis, F. A.; Towson, J. C.; Vashi, D. B.; ThimmaReddy, R.; McCauley, J. P., Jr.; Harakal, M. E.; Gosciniak, D. J. J. Org. Chem. 1990, 55, 1254. Use of this reagent generally resulted in cleaner reaction mixtures than those observed with in situ generated DMDO.
  • 34
    • 61349195547 scopus 로고    scopus 로고
    • Shortening of the reaction time to 1 h led to isolation of the desired 4e along with the corresponding 2-(7-indolyl)-2-(2-phthalimido-ethyl) indoxyl (S6e) in 97% yield (4e:S6e, 84:16).
    • Shortening of the reaction time to 1 h led to isolation of the desired 4e along with the corresponding 2-(7-indolyl)-2-(2-phthalimido-ethyl) indoxyl (S6e) in 97% yield (4e:S6e, 84:16).
  • 35
    • 61349115925 scopus 로고    scopus 로고
    • Please see Supporting Information for details
    • Please see Supporting Information for details.
  • 36
    • 38349112828 scopus 로고    scopus 로고
    • and references therein. For representative examples, see: a
    • For representative examples, see: (a) Colby Davie, E. A.; Mennen, S. M.; Xu, Y.; Miller, S. J. Chem. Rev. 2007, 107, 5759, and references therein.
    • (2007) Chem. Rev , vol.107 , pp. 5759
    • Colby Davie, E.A.1    Mennen, S.M.2    Xu, Y.3    Miller, S.J.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.