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Volumn 9, Issue 2, 2007, Pages 271-274

Flexible strategy for differentially 3,5-disubstituted 4-oxypyridin-2(1H)- ones based on site-selective Pd-catalyzed cross-coupling reactions

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; PALLADIUM; PYRIDONE DERIVATIVE;

EID: 33846581473     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062721u     Document Type: Article
Times cited : (40)

References (43)
  • 8
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    • For selected examples, see: a
    • For selected examples, see: (a) Williams, D. R.; Sit, S. Y. J. Org. Chem. 1982, 47, 2846.
    • (1982) J. Org. Chem , vol.47 , pp. 2846
    • Williams, D.R.1    Sit, S.Y.2
  • 23
    • 13644268558 scopus 로고    scopus 로고
    • For an excellent review on site-selective cross-coupling reactions of multiple halogenated heterocycles, see: Schröter, S, Stock, C, Bach, T. Tetrahedron 2005, 61, 2245
    • For an excellent review on site-selective cross-coupling reactions of multiple halogenated heterocycles, see: Schröter, S.; Stock, C.; Bach, T. Tetrahedron 2005, 61, 2245.
  • 24
    • 0036065902 scopus 로고    scopus 로고
    • Previously, the simple 3,5-dibromo-2-pyridone (3,5-dibromo-2- hydroxypyridine) failed to undergo Suzuki bis-coupling with p- methoxyphenylboronic acid: Bracher, F.; Daab, J. Eur. J. Org. Chem. 2002, 2288.
    • Previously, the simple 3,5-dibromo-2-pyridone (3,5-dibromo-2- hydroxypyridine) failed to undergo Suzuki bis-coupling with p- methoxyphenylboronic acid: Bracher, F.; Daab, J. Eur. J. Org. Chem. 2002, 2288.
  • 28
    • 33846629061 scopus 로고
    • U.S. Patent , US 3637722
    • (d) Wang, C.-S.; McGee, T. W. U.S. Patent (1972), US 3637722.
    • (1972)
    • Wang, C.-S.1    McGee, T.W.2
  • 30
    • 0030980181 scopus 로고    scopus 로고
    • This reagent is known to effect the diiodination of pyridinols: Rousseau, G, Robin, S. Tetrahedron Lett. 1997, 38, 2467
    • This reagent is known to effect the diiodination of pyridinols: Rousseau, G.; Robin, S. Tetrahedron Lett. 1997, 38, 2467.
  • 31
    • 0037100119 scopus 로고    scopus 로고
    • This reagent was introduced by Colobert and co-workers: Castanet, A.-S, Colobert, F, Broutin, P.-E. Tetrahedron Lett. 2002, 43, 5047
    • This reagent was introduced by Colobert and co-workers: Castanet, A.-S.; Colobert, F.; Broutin, P.-E. Tetrahedron Lett. 2002, 43, 5047.
  • 32
    • 33751384970 scopus 로고
    • Note that the group of Olah had previously introduced iodine(I) trifluoromethane-sulfonate as a powerful reagent for the iodination of deactivated aromatics
    • Note that the group of Olah had previously introduced iodine(I) trifluoromethane-sulfonate as a powerful reagent for the iodination of deactivated aromatics: Olah, G. A.; Wang, Q.; Sandford, G.; Surya Prakash, G. K. J. Org. Chem. 1993, 58, 3194.
    • (1993) J. Org. Chem , vol.58 , pp. 3194
    • Olah, G.A.1    Wang, Q.2    Sandford, G.3    Surya Prakash, G.K.4
  • 33
    • 33846599373 scopus 로고    scopus 로고
    • In a study toward pyridovericin, Baldwin and co-workers have examined the Suzuki coupling of the isomeric 3,5-dibromo-2,4-dimethoxypyridine with p-methoxyphenylboronic acid, which afforded a 3:1 ratio of the C5-C3 isomers. See ref 3c
    • In a study toward pyridovericin, Baldwin and co-workers have examined the Suzuki coupling of the isomeric 3,5-dibromo-2,4-dimethoxypyridine with p-methoxyphenylboronic acid, which afforded a 3:1 ratio of the C5-C3 isomers. See ref 3c.
  • 34
    • 33846611985 scopus 로고    scopus 로고
    • The structure of 3 has been secured by X-ray analysis. See Supporting Information.
    • The structure of 3 has been secured by X-ray analysis. See Supporting Information.
  • 35
    • 33846620185 scopus 로고    scopus 로고
    • TPPTS: tris(3-sulfonatophenyl)phosphane trisodium salt.
    • TPPTS: tris(3-sulfonatophenyl)phosphane trisodium salt.
  • 36
    • 33846647512 scopus 로고    scopus 로고
    • It should be noted that reaction of 3,5-dibromo-2-pyridone 2b under identical conditions proved rather sluggish and afforded inseparable mixtures of mono- and bis-arylated adducts
    • It should be noted that reaction of 3,5-dibromo-2-pyridone 2b under identical conditions proved rather sluggish and afforded inseparable mixtures of mono- and bis-arylated adducts.
  • 37
    • 0032474721 scopus 로고    scopus 로고
    • It is worth mentioning that the related C-5 (or C-3) monoarylated 4-methoxy-2-pyrones have previously been prepared by Suzuki coupling of the corresponding monohalogenated pyrones: (a) Cerezo, S.; Moreno-Mañas, M.; Pleixats, R. Tetrahedron 1998, 54, 7813.
    • It is worth mentioning that the related C-5 (or C-3) monoarylated 4-methoxy-2-pyrones have previously been prepared by Suzuki coupling of the corresponding monohalogenated pyrones: (a) Cerezo, S.; Moreno-Mañas, M.; Pleixats, R. Tetrahedron 1998, 54, 7813.
  • 38
    • 0038487718 scopus 로고    scopus 로고
    • Marrison, L. R.; Dickinson, J. M.; Fairlamb, 1. J. S. Bioorg. Med. Chem. Lett. 2003, 13, 2667.
    • (b) Marrison, L. R.; Dickinson, J. M.; Fairlamb, 1. J. S. Bioorg. Med. Chem. Lett. 2003, 13, 2667.
  • 39
    • 0029144101 scopus 로고    scopus 로고
    • Symmetrically 3,5-diarylated 2-hydroxypyridines had been previously prepared from 3,5-dihalopyridines and then converted to the corresponding pyridones: Tagat, J. R.; McCombie, S. W.; Barton, B. E.; Jackson, J.; Shortall, J. Bioorg. Med. Chem. Lett. 1995, 5, 2143. See also ref 6.
    • Symmetrically 3,5-diarylated 2-hydroxypyridines had been previously prepared from 3,5-dihalopyridines and then converted to the corresponding pyridones: Tagat, J. R.; McCombie, S. W.; Barton, B. E.; Jackson, J.; Shortall, J. Bioorg. Med. Chem. Lett. 1995, 5, 2143. See also ref 6.
  • 40
    • 0001116319 scopus 로고    scopus 로고
    • It is likely that the trimethylsilyl group is initially cleaved from the alkyne which then undergoes acidic hydrolysis to the corresponding 3-acetylpyridone. The acid-induced desilylation of silylacetylenes has been documented: Siehl, H.-U, Kaufmann, F.-P, Hori, K. J. Am. Chem. Soc. 1992, 114, 9343
    • It is likely that the trimethylsilyl group is initially cleaved from the alkyne which then undergoes acidic hydrolysis to the corresponding 3-acetylpyridone. The acid-induced desilylation of silylacetylenes has been documented: Siehl, H.-U.; Kaufmann, F.-P.; Hori, K. J. Am. Chem. Soc. 1992, 114, 9343.
  • 41
    • 4544298013 scopus 로고    scopus 로고
    • Usually, acid-promoted hydrations of alkynes require metal catalysis, typically Hg(II) salts. For a review, see: Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem., Int. Ed. 2004, 43, 3368.
    • Usually, acid-promoted hydrations of alkynes require metal catalysis, typically Hg(II) salts. For a review, see: Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem., Int. Ed. 2004, 43, 3368.
  • 43
    • 33846623812 scopus 로고    scopus 로고
    • Acetyl-4-oxypyridones have been used as intermediates in the syntheses of tenellin and ilicicolin H. See refs 2a,b
    • 3-Acetyl-4-oxypyridones have been used as intermediates in the syntheses of tenellin and ilicicolin H. See refs 2a,b. For other approaches to 3-acetyl-5-aryl-4-oxypyridones, see refs 2c and 3a,b.
    • For other approaches to 3-acetyl-5-aryl-4-oxypyridones, see refs 2c and 3a,b


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