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1
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0141471572
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note
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Over 100 ketone-containing drugs have been brought to market in the last 10 years according to the MDL Drug Data Report (electronic database).
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2
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0033582983
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Salvino, J. M.; Mervic, M.; Mason, H. J.; Kiesow, T.; Teager, D.; Airey, J.; Labaudiniere, R. J. Org. Chem. 1999, 64, 1823. O'Donnell, M. J.; Drew, M. D.; Pottorf, R. S.; Scott, W. L. J. Comb. Chem. 2000, 2, 172.
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J. Org. Chem.
, vol.64
, pp. 1823
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-
Salvino, J.M.1
Mervic, M.2
Mason, H.J.3
Kiesow, T.4
Teager, D.5
Airey, J.6
Labaudiniere, R.7
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3
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0034154193
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Salvino, J. M.; Mervic, M.; Mason, H. J.; Kiesow, T.; Teager, D.; Airey, J.; Labaudiniere, R. J. Org. Chem. 1999, 64, 1823. O'Donnell, M. J.; Drew, M. D.; Pottorf, R. S.; Scott, W. L. J. Comb. Chem. 2000, 2, 172.
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(2000)
J. Comb. Chem.
, vol.2
, pp. 172
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O'Donnell, M.J.1
Drew, M.D.2
Pottorf, R.S.3
Scott, W.L.4
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7
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84985609958
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Worster, P. M.; McArthur, C. R.; Leznoff, C. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 221.
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(1979)
Angew. Chem., Int. Ed. Engl.
, vol.18
, pp. 221
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Worster, P.M.1
McArthur, C.R.2
Leznoff, C.C.3
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8
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0001122247
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Murphy, A. M.; Dagnino, R.; Vallar, P. L.; Trippe, A. J.; Sherman, S. L. ; Lumpkin, R. H.; Tamura, S. Y.; Webb, T. R. J. Am. Chem. Soc. 1992, 114, 3156.
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(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 3156
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Murphy, A.M.1
Dagnino, R.2
Vallar, P.L.3
Trippe, A.J.4
Sherman, S.L.5
Lumpkin, R.H.6
Tamura, S.Y.7
Webb, T.R.8
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9
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0033582779
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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.
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(1999)
J. Org. Chem.
, vol.64
, pp. 1356
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-
Poupart, M.1
Fazal, G.2
Goulet, S.3
Mar, L.T.4
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10
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0141806364
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Solid-phase synthesis of biaryl aldehydes and ketones using webb's semicarbazide linker
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Anaheim, CA, March 21-25, 1999; American Chemical Society: Washington, DC
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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.
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(1999)
Book of Abstracts, 217th National Meeting of the American Chemical Society
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Giroux, A.1
Han, Y.2
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11
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0033520777
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Lee, A.; Huang, L.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 9907.
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(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 9907
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Lee, A.1
Huang, L.2
Ellman, J.A.3
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15
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0009473366
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and references therein
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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.
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(1998)
J. Org. Chem.
, vol.63
, pp. 3006
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Cho, B.R.1
Cho, N.S.2
Song, K.N.3
Kim, Y.K.4
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18
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0141806366
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note
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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.
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19
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0141583219
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note
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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.
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22
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0141471570
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note
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-1.
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23
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37049078993
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Prepared in high yield from 4-bromo-2-fluorobenzonitrile by palladium-mediated methoxy carbonylation. Dufaud, V.; Thivolle-Cazat, J.; Basset, J. M. J. Chem. Soc., Chem. Commun. 1990, 426.
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(1990)
J. Chem. Soc., Chem. Commun.
, pp. 426
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Dufaud, V.1
Thivolle-Cazat, J.2
Basset, J.M.3
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24
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0026124845
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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.
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(1991)
Biotechnol. Prog.
, vol.7
, pp. 111
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Wang, S.1
Foutch, G.L.2
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25
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0024904021
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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.
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(1989)
Chem. Eng. Sci.
, vol.44
, pp. 2760
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Chen, W.Y.1
Foutch, G.L.2
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26
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0141471571
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note
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The treatment of resin 10 with TFA/H20 at 55 °C for 24 h led to no appreciable decomposition.
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