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For Pd-free synthesis of 2-arylbenzo[b]furans via Cu-catalyzed reaction see: and references cited therein
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For Pd-free synthesis of 2-arylbenzo[b]furans via Cu-catalyzed reaction see: Bates C.G., Saejueng P., Murphy J.M., Venkataraman D. Org. Lett. 4:2002;4727-4729. and references cited therein.
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The o-hydroxytolan IIIaa isolated was found to be a stable compound and no spontaneous cyclization was observed upon storage at room temperature as reported earlier in other cases. For example o-hydroxytolan used for the synthesis of XH-14, a benzofuran derivative isolated from the plant Salvia miltiorrhiza, showed a strong tendency to cyclize even upon storage at 4°C. See Lutjens, H.; Scammells, P. J. Synlett 1999, 1079-1081.
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For alternative access to nitrobenzo[b]furans via intramolecular condensation of suitably substituted nitrobenzenes, including intramolecular Wittig olefinations, see
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Synthesis via direct nitration of benzo[b]furans often gives a mixture of isomers. See, for example: (a) Graham, S. L.; Hoffman, J. M.; Gautheron, P.; Michelson, S. R.; Scholz, T. H.; Schwam, H.; Shepard, K. L.; Smith, A. M.; Smith, R. L.; Sondey, J. M.; Sugrue, M. F. J. Med. Chem. 1990, 33, 749-754. For alternative access to nitrobenzo[b]furans via intramolecular condensation of suitably substituted nitrobenzenes, including intramolecular Wittig olefinations, see: (b) Chilin, A.; Rodighiero, P.; Guitto, A. Synthesis 1998, 309-313; (c) Kaminsky, D.; Shavel, F.; Meitzer, I. Tetrahedron Lett. 1967, 859-861; (d) Mooradian, A. Tetrahedron Lett. 1967, 407-408. (e) Mooradian, A.; Dupont, P. E. J. Heterocycl. Chem. 1967, 4, 441-444.
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57
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0031931067
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Synthesis via direct nitration of benzo[b]furans often gives a mixture of isomers. See, for example: (a) Graham, S. L.; Hoffman, J. M.; Gautheron, P.; Michelson, S. R.; Scholz, T. H.; Schwam, H.; Shepard, K. L.; Smith, A. M.; Smith, R. L.; Sondey, J. M.; Sugrue, M. F. J. Med. Chem. 1990, 33, 749-754. For alternative access to nitrobenzo[b]furans via intramolecular condensation of suitably substituted nitrobenzenes, including intramolecular Wittig olefinations, see: (b) Chilin, A.; Rodighiero, P.; Guitto, A. Synthesis 1998, 309-313; (c) Kaminsky, D.; Shavel, F.; Meitzer, I. Tetrahedron Lett. 1967, 859-861; (d) Mooradian, A. Tetrahedron Lett. 1967, 407-408. (e) Mooradian, A.; Dupont, P. E. J. Heterocycl. Chem. 1967, 4, 441-444.
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Chilin, A.1
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0011414135
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Synthesis via direct nitration of benzo[b]furans often gives a mixture of isomers. See, for example: (a) Graham, S. L.; Hoffman, J. M.; Gautheron, P.; Michelson, S. R.; Scholz, T. H.; Schwam, H.; Shepard, K. L.; Smith, A. M.; Smith, R. L.; Sondey, J. M.; Sugrue, M. F. J. Med. Chem. 1990, 33, 749-754. For alternative access to nitrobenzo[b]furans via intramolecular condensation of suitably substituted nitrobenzenes, including intramolecular Wittig olefinations, see: (b) Chilin, A.; Rodighiero, P.; Guitto, A. Synthesis 1998, 309-313; (c) Kaminsky, D.; Shavel, F.; Meitzer, I. Tetrahedron Lett. 1967, 859-861; (d) Mooradian, A. Tetrahedron Lett. 1967, 407-408. (e) Mooradian, A.; Dupont, P. E. J. Heterocycl. Chem. 1967, 4, 441-444.
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Kaminsky, D.1
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0002318130
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Synthesis via direct nitration of benzo[b]furans often gives a mixture of isomers. See, for example: (a) Graham, S. L.; Hoffman, J. M.; Gautheron, P.; Michelson, S. R.; Scholz, T. H.; Schwam, H.; Shepard, K. L.; Smith, A. M.; Smith, R. L.; Sondey, J. M.; Sugrue, M. F. J. Med. Chem. 1990, 33, 749-754. For alternative access to nitrobenzo[b]furans via intramolecular condensation of suitably substituted nitrobenzenes, including intramolecular Wittig olefinations, see: (b) Chilin, A.; Rodighiero, P.; Guitto, A. Synthesis 1998, 309-313; (c) Kaminsky, D.; Shavel, F.; Meitzer, I. Tetrahedron Lett. 1967, 859-861; (d) Mooradian, A. Tetrahedron Lett. 1967, 407-408. (e) Mooradian, A.; Dupont, P. E. J. Heterocycl. Chem. 1967, 4, 441-444.
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Mooradian, A.1
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84981855973
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Synthesis via direct nitration of benzo[b]furans often gives a mixture of isomers. See, for example: (a) Graham, S. L.; Hoffman, J. M.; Gautheron, P.; Michelson, S. R.; Scholz, T. H.; Schwam, H.; Shepard, K. L.; Smith, A. M.; Smith, R. L.; Sondey, J. M.; Sugrue, M. F. J. Med. Chem. 1990, 33, 749-754. For alternative access to nitrobenzo[b]furans via intramolecular condensation of suitably substituted nitrobenzenes, including intramolecular Wittig olefinations, see: (b) Chilin, A.; Rodighiero, P.; Guitto, A. Synthesis 1998, 309-313; (c) Kaminsky, D.; Shavel, F.; Meitzer, I. Tetrahedron Lett. 1967, 859-861; (d) Mooradian, A. Tetrahedron Lett. 1967, 407-408. (e) Mooradian, A.; Dupont, P. E. J. Heterocycl. Chem. 1967, 4, 441-444.
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Dupont, P.E.2
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63
-
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0000906980
-
-
All the terminal alkynes used are commercially available
-
5 requires C, 63.36; H, 5.65%.
-
-
-
-
64
-
-
0000906980
-
-
note
-
5 requires C, 63.36; H, 5.65%.
-
-
-
-
65
-
-
84988204469
-
-
Use of other amine bases e.g. DBU, DBACO, DBN etc. in Sonogashira-type reactions has been previously reported
-
(a) Carpita, A.; Lessi, A.; Rossi, R. Synthesis 1984, 571-572. Use of other amine bases e.g. DBU, DBACO, DBN etc. in Sonogashira-type reactions has been previously reported:
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Carpita, A.1
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0037136485
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(c) Mio, M. J.; Kopel, L. C.; Braun, J. B.; Gadzikwa, T. L.; Hull, K. L. ; Brisbois, R. G.; Markworth, C. J.; Grieco, P. A. Org. Lett. 2002, 4, 3199-3202.
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0034598318
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Compound IIIb has been converted to a benzofuro[3,2-c]pyridine as a potential antidepressant. See: Kennis, L. E. J.; Bischoff, F. P.; Mertens, C. J.; Love, C. J.; Van den Keybus, F. A. F.; Pieters, S.; Braeken, M.; Megens, A. A. H. P.; Leysen, J. E. Bioorg. Med. Chem. Lett. 2000, 71-74.
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Leysen, J.E.9
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