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Volumn 5, Issue 1, 2003, Pages 7-10

Application of aryloximes as solid-phase ketone linkers

Author keywords

[No Author keywords available]

Indexed keywords

ANION; BENZONITRILE; KETONE DERIVATIVE; OXIME DERIVATIVE; RESIN; KETONE; NITRILE; OXIME;

EID: 0038187683     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026913a     Document Type: Article
Times cited : (15)

References (27)
  • 1
    • 0141471572 scopus 로고    scopus 로고
    • note
    • Over 100 ketone-containing drugs have been brought to market in the last 10 years according to the MDL Drug Data Report (electronic database).
  • 3
  • 9
    • 0033582779 scopus 로고    scopus 로고
    • Poupart, M.; Fazal, G.; Goulet, S.; Mar, L. T. J. Org. Chem. 1999, 64, 1356. The Webb linker has also been recently used with nonfluorinated ketones; see: Giroux, A.; Han, Y. Solid-Phase Synthesis of Biaryl Aldehydes and Ketones Using Webb's Semicarbazide Linker. Book of Abstracts, 217th National Meeting of the American Chemical Society, Anaheim, CA, March 21-25, 1999; American Chemical Society: Washington, DC; 1999.
    • (1999) J. Org. Chem. , vol.64 , pp. 1356
    • Poupart, M.1    Fazal, G.2    Goulet, S.3    Mar, L.T.4
  • 10
    • 0141806364 scopus 로고    scopus 로고
    • Solid-phase synthesis of biaryl aldehydes and ketones using webb's semicarbazide linker
    • Anaheim, CA, March 21-25, 1999; American Chemical Society: Washington, DC
    • Poupart, M.; Fazal, G.; Goulet, S.; Mar, L. T. J. Org. Chem. 1999, 64, 1356. The Webb linker has also been recently used with nonfluorinated ketones; see: Giroux, A.; Han, Y. Solid-Phase Synthesis of Biaryl Aldehydes and Ketones Using Webb's Semicarbazide Linker. Book of Abstracts, 217th National Meeting of the American Chemical Society, Anaheim, CA, March 21-25, 1999; American Chemical Society: Washington, DC; 1999.
    • (1999) Book of Abstracts, 217th National Meeting of the American Chemical Society
    • Giroux, A.1    Han, Y.2
  • 15
    • 0009473366 scopus 로고    scopus 로고
    • and references therein
    • Aldehyde oximes were not studied since their corresponding aryloxime adducts are unstable to the basic conditions used in the SNAr reaction leading to the formation of nitriles; see: Cho, B. R.; Cho, N. S.; Song, K. N.; Kim, Y. K. J. Org. Chem. 1998, 63, 3006 and references therein.
    • (1998) J. Org. Chem. , vol.63 , pp. 3006
    • Cho, B.R.1    Cho, N.S.2    Song, K.N.3    Kim, Y.K.4
  • 18
    • 0141806366 scopus 로고    scopus 로고
    • note
    • All oximes were prepared in near quantitative yields from the corresponding ketones by treatment with hydroxylamine hydrochloride (1.2 equiv) and pyridine (2.0 equiv) in refluxing ethanol.
  • 19
    • 0141583219 scopus 로고    scopus 로고
    • note
    • Aminobenisoxazole 5 was conveniently removed from the crude product mixture by filtration through an acidified SCX column. Interestingly, heterocycle 6 was not retained on the column. Presumably, the electron-donating character of the methoxy group in 5 increases the basicity of the 3-amine relative to 6, allowing it to ionize on the SCX column.
  • 22
    • 0141471570 scopus 로고    scopus 로고
    • note
    • -1.
  • 24
    • 0026124845 scopus 로고
    • For a discussion of differences in the kinetics of solid- versus solution-phase reactions, see: Wang, S.; Foutch, G. L. Biotechnol. Prog. 1991, 7, 111. Chen, W. Y.; Foutch, G. L. Chem. Eng. Sci. 1989, 44, 2760.
    • (1991) Biotechnol. Prog. , vol.7 , pp. 111
    • Wang, S.1    Foutch, G.L.2
  • 25
    • 0024904021 scopus 로고
    • For a discussion of differences in the kinetics of solid- versus solution-phase reactions, see: Wang, S.; Foutch, G. L. Biotechnol. Prog. 1991, 7, 111. Chen, W. Y.; Foutch, G. L. Chem. Eng. Sci. 1989, 44, 2760.
    • (1989) Chem. Eng. Sci. , vol.44 , pp. 2760
    • Chen, W.Y.1    Foutch, G.L.2
  • 26
    • 0141471571 scopus 로고    scopus 로고
    • note
    • The treatment of resin 10 with TFA/H20 at 55 °C for 24 h led to no appreciable decomposition.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.