-
1
-
-
33645994158
-
-
(a) Jayasinghe, L.; Abbas, H. K.; Jacob, M. R.; Herath, W. H. M. W.; Nanayakkara, N. P. D. J. Nat. Prod 2006, 69, 439.
-
(2006)
J. Nat. Prod
, vol.69
, pp. 439
-
-
Jayasinghe, L.1
Abbas, H.K.2
Jacob, M.R.3
Herath, W.H.M.W.4
Nanayakkara, N.P.D.5
-
2
-
-
1542335671
-
-
(b) Gutierrez-Cirlos, E. B.; Merbitz-Zahradnik, T.; Trumpower, B. L. J. Biol. Chem. 2004, 279, 8708.
-
(2004)
J. Biol. Chem
, vol.279
, pp. 8708
-
-
Gutierrez-Cirlos, E.B.1
Merbitz-Zahradnik, T.2
Trumpower, B.L.3
-
3
-
-
0037451820
-
-
(c) Zhang, C.; Jin, L.; Mondie, B.; Mitchell, S. S.; Castelhano, A. L.; Cai, W.; Bergenhem, N. Bioorg. Med. Chem. Lett. 2003, 13, 1433.
-
(2003)
Bioorg. Med. Chem. Lett
, vol.13
, pp. 1433
-
-
Zhang, C.1
Jin, L.2
Mondie, B.3
Mitchell, S.S.4
Castelhano, A.L.5
Cai, W.6
Bergenhem, N.7
-
4
-
-
0037350776
-
-
(d) Schmidt, K.; Riese, U.; Li, Z.; Hamburger, M. J. Nat. Prod. 2003, 66, 378.
-
(2003)
J. Nat. Prod
, vol.66
, pp. 378
-
-
Schmidt, K.1
Riese, U.2
Li, Z.3
Hamburger, M.4
-
5
-
-
0036171165
-
-
(e) Sakemi, S.; Bordner, J.; DeCosta, D. L.; Dekker, K. A.; Hirai, H.; Inagaki, T.; Kim, Y.-J.; Kojima, N.; Sims, J. C.; Sugie, Y.; Sugiura, A.; Sutcliffe, J. A.; Tachikawa, K.; Truesdell, S. J.; Wong, J. W.; Yoshikawa, N.; Kojima, Y. J. Antibiot. 2002, 55, 6.
-
(2002)
J. Antibiot
, vol.55
, pp. 6
-
-
Sakemi, S.1
Bordner, J.2
DeCosta, D.L.3
Dekker, K.A.4
Hirai, H.5
Inagaki, T.6
Kim, Y.-J.7
Kojima, N.8
Sims, J.C.9
Sugie, Y.10
Sugiura, A.11
Sutcliffe, J.A.12
Tachikawa, K.13
Truesdell, S.J.14
Wong, J.W.15
Yoshikawa, N.16
Kojima, Y.17
-
6
-
-
0034985518
-
-
(f) Hirano, N.; Kohno, J.; Tsunoda, S.; Nishio, M.; Kishi, N.; Okuda, T.; Kawano, K.; Komatsubara, S.; Nakanishi, N. J. Antibiot. 2001, 54, 421.
-
(2001)
J. Antibiot
, vol.54
, pp. 421
-
-
Hirano, N.1
Kohno, J.2
Tsunoda, S.3
Nishio, M.4
Kishi, N.5
Okuda, T.6
Kawano, K.7
Komatsubara, S.8
Nakanishi, N.9
-
7
-
-
0031730579
-
-
(g) Takahashi, S.; Uchida, K.; Kakinuma, N.; Hashimoto, R.; Yanagisawa, T.; Nakagawa, A. J. Antibiot. 1998, 51, 1051.
-
(1998)
J. Antibiot
, vol.51
, pp. 1051
-
-
Takahashi, S.1
Uchida, K.2
Kakinuma, N.3
Hashimoto, R.4
Yanagisawa, T.5
Nakagawa, A.6
-
8
-
-
0001426679
-
-
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
-
9
-
-
0021887740
-
-
(b) Williams, D. R.; Bremmer, M. L.; Brown, D. L.; D'Antuono, J. J. Org. Chem. 1985, 50, 2807.
-
(1985)
J. Org. Chem
, vol.50
, pp. 2807
-
-
Williams, D.R.1
Bremmer, M.L.2
Brown, D.L.3
D'Antuono, J.4
-
12
-
-
37049073584
-
-
(e) Buck, J.; Madeley, J. P.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1992, 67.
-
(1992)
J. Chem. Soc., Perkin Trans. 1
, pp. 67
-
-
Buck, J.1
Madeley, J.P.2
Pattenden, G.3
-
15
-
-
0037157184
-
-
(h) Zhang, Q.; Rivkin, A.; Curran, D. P. J. Am. Chem. Soc. 2002, 124, 5774.
-
(2002)
J. Am. Chem. Soc
, vol.124
, pp. 5774
-
-
Zhang, Q.1
Rivkin, A.2
Curran, D.P.3
-
16
-
-
4544287532
-
-
(i) Fürstner, A.; Feyen, F.; Prinz, H.; Waldmann, H. Tetrahedron 2004, 60, 9543.
-
(2004)
Tetrahedron
, vol.60
, pp. 9543
-
-
Fürstner, A.1
Feyen, F.2
Prinz, H.3
Waldmann, H.4
-
18
-
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(a) Jones, R. C. F.; Bhalay, G.; Carter, P. A.; Duller, K. A. M.; Dunn, S. H. J. Chem. Soc., Perkin Trans. 1 1999, 765.
-
(1999)
J. Chem. Soc., Perkin Trans. 1
, pp. 765
-
-
Jones, R.C.F.1
Bhalay, G.2
Carter, P.A.3
Duller, K.A.M.4
Dunn, S.H.5
-
19
-
-
0141741539
-
-
(b) Rao Irlapati, N.; Baldwin, J. E.; Adlington, R. M.; Pritchard, G. J.; Cowley, A. Org. Lett. 2003, 5, 2351.
-
(2003)
Org. Lett
, vol.5
, pp. 2351
-
-
Rao Irlapati, N.1
Baldwin, J.E.2
Adlington, R.M.3
Pritchard, G.J.4
Cowley, A.5
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20
-
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-
-
(c) Rao Irlapati, N.; Adlington, R. M.; Conte, A.; Pritchard, G. J.; Marquez, R.; Baldwin, J. E. Tetrahedron 2004, 60, 9307.
-
(2004)
Tetrahedron
, vol.60
, pp. 9307
-
-
Rao Irlapati, N.1
Adlington, R.M.2
Conte, A.3
Pritchard, G.J.4
Marquez, R.5
Baldwin, J.E.6
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21
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0141630849
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For previous reports from this group, see: a
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For previous reports from this group, see: (a) Bossharth, E.; Desbordes, P.; Monteiro, N.; Balme, G. Org. Lett. 2003, 5, 2441.
-
(2003)
Org. Lett
, vol.5
, pp. 2441
-
-
Bossharth, E.1
Desbordes, P.2
Monteiro, N.3
Balme, G.4
-
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-
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(b) Aillaud, I.; Bossharth, E.; Conreaux, D.; Desbordes, P.; Monteiro, N.; Balme, G. Org. Lett. 2006, 8, 1113.
-
(2006)
Org. Lett
, vol.8
, pp. 1113
-
-
Aillaud, I.1
Bossharth, E.2
Conreaux, D.3
Desbordes, P.4
Monteiro, N.5
Balme, G.6
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23
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13644268558
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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
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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.
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24
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0036065902
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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.
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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.
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27
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33847600768
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(c) den Hertog, H. J.; Combe, W. P.; Kolder, C. R. Recl. Trav. Chim. 1954, 73, 704.
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(1954)
Recl. Trav. Chim
, vol.73
, pp. 704
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den Hertog, H.J.1
Combe, W.P.2
Kolder, C.R.3
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28
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33846629061
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U.S. Patent , US 3637722
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(d) Wang, C.-S.; McGee, T. W. U.S. Patent (1972), US 3637722.
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(1972)
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Wang, C.-S.1
McGee, T.W.2
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0029145174
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Devadas, B.; Rogers, T. E.; Gray, S. H. Synth. Commun. 1995, 25, 3199.
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(1995)
Synth. Commun
, vol.25
, pp. 3199
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Devadas, B.1
Rogers, T.E.2
Gray, S.H.3
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30
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0030980181
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This reagent is known to effect the diiodination of pyridinols: Rousseau, G, Robin, S. Tetrahedron Lett. 1997, 38, 2467
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This reagent is known to effect the diiodination of pyridinols: Rousseau, G.; Robin, S. Tetrahedron Lett. 1997, 38, 2467.
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31
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0037100119
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This reagent was introduced by Colobert and co-workers: Castanet, A.-S, Colobert, F, Broutin, P.-E. Tetrahedron Lett. 2002, 43, 5047
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This reagent was introduced by Colobert and co-workers: Castanet, A.-S.; Colobert, F.; Broutin, P.-E. Tetrahedron Lett. 2002, 43, 5047.
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32
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33751384970
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Note that the group of Olah had previously introduced iodine(I) trifluoromethane-sulfonate as a powerful reagent for the iodination of deactivated aromatics
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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.
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(1993)
J. Org. Chem
, vol.58
, pp. 3194
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Olah, G.A.1
Wang, Q.2
Sandford, G.3
Surya Prakash, G.K.4
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33846599373
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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
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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.
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34
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33846611985
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The structure of 3 has been secured by X-ray analysis. See Supporting Information.
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The structure of 3 has been secured by X-ray analysis. See Supporting Information.
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35
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33846620185
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TPPTS: tris(3-sulfonatophenyl)phosphane trisodium salt.
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TPPTS: tris(3-sulfonatophenyl)phosphane trisodium salt.
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36
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33846647512
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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
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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.
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37
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0032474721
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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.
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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.
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38
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0038487718
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Marrison, L. R.; Dickinson, J. M.; Fairlamb, 1. J. S. Bioorg. Med. Chem. Lett. 2003, 13, 2667.
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(b) Marrison, L. R.; Dickinson, J. M.; Fairlamb, 1. J. S. Bioorg. Med. Chem. Lett. 2003, 13, 2667.
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0029144101
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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.
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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.
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0001116319
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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
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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.
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41
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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.
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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.
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For metal-free methods, see:, and references therein
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For metal-free methods, see: Olivi, N.; Thomas, E.; Peyrat, J.-F.; Alami, M.; Brion, J.-D. Synlett 2004, 2175 and references therein.
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(2004)
Synlett
, pp. 2175
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Olivi, N.1
Thomas, E.2
Peyrat, J.-F.3
Alami, M.4
Brion, J.-D.5
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43
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Acetyl-4-oxypyridones have been used as intermediates in the syntheses of tenellin and ilicicolin H. See refs 2a,b
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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.
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For other approaches to 3-acetyl-5-aryl-4-oxypyridones, see refs 2c and 3a,b
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