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For recent illustrations, see the following reviews:a
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For recent illustrations, see the following reviews:(a) McGuigan, C.; Balzarini, J. Antiviral Res. 2006, 71, 149.
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McGuigan, C.1
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(b) Kim, S.; Salim, A. A.; Swanson, S. M.; Kinghorn, A. D. Anti-Cancer Agents Med. Chem. 2006, 6, 319.
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Anti-Cancer Agents Med. Chem
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Kim, S.1
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(d) Santana, L.; Uriarte, E.; Roleira, F.; Milhares, N.; Borges, F. Curr. Med. Chem. 2004, 11, 3239.
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Santana, L.1
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Borges, F.5
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33748587610
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For recent contributions, see:a
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For recent contributions, see:(a) Kundu, N. G.; Pal, M.; Mahanty, J. S.; De, M. J. Chem. Soc., Perkin Trans. 1 1997, 2815.
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Kundu, N.G.1
Pal, M.2
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De, M.4
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(b) Arcadi, A.; Cacchi, S.; Di Giuseppe, S.; Fabrizi, G.; Marinelli, F. Synlett 2002, 453.
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Synlett
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Arcadi, A.1
Cacchi, S.2
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Fabrizi, G.4
Marinelli, F.5
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28844489157
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(e) Li, X.; Chianese, A. R.; Vogel, T.; Crabtree, R. H. Org. Lett. 2005, 7, 5437.
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Org. Lett
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Li, X.1
Chianese, A.R.2
Vogel, T.3
Crabtree, R.H.4
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33748309418
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(g) Venkataraman, S.; Barange, D. K.; Pal, M. Tetrahedron Lett. 2006, 47, 7317.
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(2006)
Tetrahedron Lett
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Venkataraman, S.1
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Pal, M.3
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14
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34250867364
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(b) Oppenheimer, J.; Johnson, W. L.; Tracey, M. R.; Hsung, R. P.; Yao, P.-Y.; Liu, R.; Zhao, K. Org. Lett. 2007, 9, 2361.
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Org. Lett
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Oppenheimer, J.1
Johnson, W.L.2
Tracey, M.R.3
Hsung, R.P.4
Yao, P.-Y.5
Liu, R.6
Zhao, K.7
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15
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0034607711
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See also: c
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See also: (c) Godt, A.; Ünsal, Ö.; Roos, M. J. Org. Chem. 2000, 65, 2837.
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J. Org. Chem
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Godt, A.1
Ünsal, O.2
Roos, M.3
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17
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0013567167
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For general reviews on dealkylation of ethers, see:a
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For general reviews on dealkylation of ethers, see:(a) Ranu, B. C.; Bhar, S. Org. Prep. Proced. Int. 1996, 28, 371.
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(1996)
Org. Prep. Proced. Int
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, pp. 371
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Ranu, B.C.1
Bhar, S.2
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21
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0030446401
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2-Alkynylphenols are known to undergo facile cycloisomerization under alkaline conditions. For a leading reference, see: Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280.
-
2-Alkynylphenols are known to undergo facile cycloisomerization under alkaline conditions. For a leading reference, see: Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280.
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22
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33846581473
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Conreaux, D.; Bossharth, E.; Monteiro, N.; Desbordes, P.; Vors, J.-P.; Balme, G. Org. Lett. 2007, 9, 271.
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(2007)
Org. Lett
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, pp. 271
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Conreaux, D.1
Bossharth, E.2
Monteiro, N.3
Desbordes, P.4
Vors, J.-P.5
Balme, G.6
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23
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4444283259
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The related, naturally occurring 7-phenyldihydrofuro[3,2-c] pyridin-4-ones have been the focus of recent attention:(a) Snider, B. B.; Che, G Org. Lett. 2004, 6, 2877.
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The related, naturally occurring 7-phenyldihydrofuro[3,2-c] pyridin-4-ones have been the focus of recent attention:(a) Snider, B. B.; Che, G Org. Lett. 2004, 6, 2877.
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25
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55249124121
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So far, only one example of a similar process has been reported in the literature which refers to the formation in low yield of a furo[3,2-c] quinolin-4-one during the reaction of a 3-bromo-4-methoxyquinolin-2-one with a copper acetylide: Gaston, J. L.; Greer, R. J.; Grundon, M. F. J. Chem. Res., Synop. 1985, 135.
-
So far, only one example of a similar process has been reported in the literature which refers to the formation in low yield of a furo[3,2-c] quinolin-4-one during the reaction of a 3-bromo-4-methoxyquinolin-2-one with a copper acetylide: Gaston, J. L.; Greer, R. J.; Grundon, M. F. J. Chem. Res., Synop. 1985, 135.
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26
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55249102775
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The coupling reaction is normally achieved in less than 16 h at 60°C to give 4a in up to 81% isolated yield.
-
The coupling reaction is normally achieved in less than 16 h at 60°C to give 4a in up to 81% isolated yield.
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27
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55249123230
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3N/DMF (2:1) was submitted to microwave irradiation (CEM Discover apparatus; settings 120°C, 150W) during 6 h to give the corresponding furan derivative 3b in 81% isolated yield.
-
3N/DMF (2:1) was submitted to microwave irradiation (CEM Discover apparatus; settings 120°C, 150W) during 6 h to give the corresponding furan derivative 3b in 81% isolated yield.
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-
-
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28
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55249087726
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The slow convertion rate may be explained by increased steric hindrance around the methoxy group
-
The slow convertion rate may be explained by increased steric hindrance around the methoxy group.
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29
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55249087057
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See Supporting information
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See Supporting information.
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31
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33845183073
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For a more recent leading reference, see: b
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For a more recent leading reference, see: (b) Strauss, M.; Torres, R. J. Org. Chem. 1989, 54, 756.
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J. Org. Chem
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Strauss, M.1
Torres, R.2
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32
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0034048676
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Scarce examples of nucleophilic O-dealkylations have also been reported to occur in the presence of primary and secondary aliphatic amines under high reaction temperatures (150-200°C, a) Nishioka, H, Nagasawa, M, Yoshida, K. Synthesis 2000, 243
-
Scarce examples of nucleophilic O-dealkylations have also been reported to occur in the presence of primary and secondary aliphatic amines under high reaction temperatures (150-200°C):(a) Nishioka, H.; Nagasawa, M.; Yoshida, K. Synthesis 2000, 243.
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33
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14644388720
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(b) Shcherbakova, I.; Balandrin, M. F.; Fox, J.; Ghatak, A.; Heaton, W. L.; Conklin, R. L. Bioorg. Med. Chem. Lett. 2005, 15, 1557.
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(2005)
Bioorg. Med. Chem. Lett
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, pp. 1557
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Shcherbakova, I.1
Balandrin, M.F.2
Fox, J.3
Ghatak, A.4
Heaton, W.L.5
Conklin, R.L.6
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34
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33846064670
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Protonation may occur spontaneously due to the probable presence of water as contaminant in the system or during workup. When used as solvent, MeCN may also intervene as a proton source owing to the predictable high basicity of the furan 2-anion:Shen, K, Fu, Y, Li, J.-N, Liu, L, Guo, Q.-X. Tetrahedron 2007, 63, 1568
-
Protonation may occur spontaneously due to the probable presence of water as contaminant in the system or during workup. When used as solvent, MeCN may also intervene as a proton source owing to the predictable high basicity of the furan 2-anion:Shen, K.; Fu, Y.; Li, J.-N.; Liu, L.; Guo, Q.-X. Tetrahedron 2007, 63, 1568.
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35
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0141630849
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Previous investigations from the same laboratories have demonstrated the selective synthesis of furopyridones of type 11 through electrophilic annulation/dealkylation reactions of 4-alkoxy-3-alkynyl-2-pyridones:(a) Bossharth, E, Desbordes, P, Monteiro, N, Balme, G Org. Lett. 2003, 5, 2441
-
Previous investigations from the same laboratories have demonstrated the selective synthesis of furopyridones of type 11 through electrophilic annulation/dealkylation reactions of 4-alkoxy-3-alkynyl-2-pyridones:(a) Bossharth, E.; Desbordes, P.; Monteiro, N.; Balme, G Org. Lett. 2003, 5, 2441.
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36
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33646453634
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(b) Aillaud, I.; Bossharth, E.; Conreaux, D.; Desbordes, P.; Monteiro, N.; Balme, G. Org. Lett. 2006, 8, 1113.
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Org. Lett
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, pp. 1113
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Aillaud, I.1
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Conreaux, D.3
Desbordes, P.4
Monteiro, N.5
Balme, G.6
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37
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0032474721
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Cerezo, S.; Moreno-Mañas, M.; Pleixats, R. Tetrahedron 1998, 54, 7813.
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Tetrahedron
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Cerezo, S.1
Moreno-Mañas, M.2
Pleixats, R.3
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38
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33947545753
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This structure is rather uncommon but may be found in natural products: (a) Wang, Y, Shang, X.-Y, Wang, S.-J, Mo, S.-Y, Li, S, Yang, Y.-C, Ye, F, Shi, J.-G, He, L. J. Nat. Prod. 2007, 70, 296
-
This structure is rather uncommon but may be found in natural products: (a) Wang, Y.; Shang, X.-Y.; Wang, S.-J.; Mo, S.-Y.; Li, S.; Yang, Y.-C.; Ye, F.; Shi, J.-G.; He, L. J. Nat. Prod. 2007, 70, 296.
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40
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33645080180
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Furocoumarins:(a) Wang, X.; Nakagawa-Goto, K.; Kozuka, M.; Tokuda, H.; Nishino, H.; Lee, K.-H. Pharm. Biol. 2006, 44, 116.
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Furocoumarins:(a) Wang, X.; Nakagawa-Goto, K.; Kozuka, M.; Tokuda, H.; Nishino, H.; Lee, K.-H. Pharm. Biol. 2006, 44, 116.
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41
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(b) Mulholland, D. A.; Iourine, S. E.; Taylor, D. A. H.; Dean, F. M. Phytochemistry 1998, 47, 1641.
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Phytochemistry
, vol.47
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Mulholland, D.A.1
Iourine, S.E.2
Taylor, D.A.H.3
Dean, F.M.4
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42
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16644367430
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Dihydrofurocoumarins: (c) Motai, T.; Kitanaka, S. Chem. Pharm. Bull. 2004, 52, 1215.
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Dihydrofurocoumarins: (c) Motai, T.; Kitanaka, S. Chem. Pharm. Bull. 2004, 52, 1215.
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43
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0032191056
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(d) Lee, Y. R.; Kim, B. S.; Wang, H. C Tetrahedron 1998, 54, 12215.
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(1998)
Tetrahedron
, vol.54
, pp. 12215
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Lee, Y.R.1
Kim, B.S.2
Wang, H.C.3
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44
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33750065138
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Coumestans: e
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Coumestans: (e) Pôças, E. S. C.; Lopes, D. V. S.; da Silva, A. J. M.; Pimenta, P. H. C.; Leitão, F. B.; Netto, C. D.; Buarque, C. D.; Brito, F. V.; Costa, P. R. R.; Noël, F. Bioorg. Med. Chem. 2006, 14, 7962.
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Bioorg. Med. Chem
, vol.14
, pp. 7962
-
-
Pôças, E.S.C.1
Lopes, D.V.S.2
da Silva, A.J.M.3
Pimenta, P.H.C.4
Leitão, F.B.5
Netto, C.D.6
Buarque, C.D.7
Brito, F.V.8
Costa, P.R.R.9
Noël, F.10
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45
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0035847676
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(f) da Silva, A. J. M.; Melo, P. A.; Silva, N. M. V.; Brito, F. V.; Buarque, C. D.; de Souza, D. V.; Rodrigues, V. P.; Pocas, E. S. C.; Noel, F.; Albuquerque, E. X.; Costa, P. R. R. Bioorg. Med. Chem. Lett. 2001, 11, 283.
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Bioorg. Med. Chem. Lett
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, pp. 283
-
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da Silva, A.J.M.1
Melo, P.A.2
Silva, N.M.V.3
Brito, F.V.4
Buarque, C.D.5
de Souza, D.V.6
Rodrigues, V.P.7
Pocas, E.S.C.8
Noel, F.9
Albuquerque, E.X.10
Costa, P.R.R.11
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46
-
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0037128463
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-
In many cases, mixtures of isomeric furo[3,2-c]coumarins and furo[3,2-b]chromones have been previously obtained:(a) Lee, Y. R.; Suk, J. Y. Tetrahedron 2002, 58, 2359.
-
In many cases, mixtures of isomeric furo[3,2-c]coumarins and furo[3,2-b]chromones have been previously obtained:(a) Lee, Y. R.; Suk, J. Y. Tetrahedron 2002, 58, 2359.
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47
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0035029756
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(b) Tollari, S.; Palmisano, G.; Cenini, S.; Cravotto, G.; Giovenzana, G. B.; Penoni, A. Synthesis 2001, 735.
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(2001)
Synthesis
, pp. 735
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Tollari, S.1
Palmisano, G.2
Cenini, S.3
Cravotto, G.4
Giovenzana, G.B.5
Penoni, A.6
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48
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0033378053
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(c) Kobayashi, K.; Sakashita, K.; Akamatsu, H.; Tanaka, K.; Uchida, M.; Uneda, T.; Kitamura, T.; Morikawa, O.; Konishi, H. Heterocycles 1999, 51, 2881.
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Kobayashi, K.1
Sakashita, K.2
Akamatsu, H.3
Tanaka, K.4
Uchida, M.5
Uneda, T.6
Kitamura, T.7
Morikawa, O.8
Konishi, H.9
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49
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0005613723
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(d) Lee, Y. R.; Byun, M. W.; Kim, B. S. Bull. Korean Chem. Soc. 1998, 19, 1080.
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Bull. Korean Chem. Soc
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, pp. 1080
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Lee, Y.R.1
Byun, M.W.2
Kim, B.S.3
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(e) Lee, Y. R.; Kim, B. S.; Wang, H. C. Tetrahedron 1998, 54, 12215.
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Lee, Y.R.1
Kim, B.S.2
Wang, H.C.3
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51
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For a recent, selective approach to furo[3,2-c]coumarins, see: (f) Cheng, G.; Hu, Y. Chem. Commun. 2007, 3285.
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For a recent, selective approach to furo[3,2-c]coumarins, see: (f) Cheng, G.; Hu, Y. Chem. Commun. 2007, 3285.
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