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Furans and their benzo derivatives: (iii) Synthesis and applications
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Katritzky, A. R., Ed.; Pergamon: New York
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(a) Donelly, D. M. X.; Meegan, M. J. Furans and Their Benzo Derivatives: (iii) Synthesis and Applications. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Ed.; Pergamon: New York, 1984; Vol. 4, pp 657-712.
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Comprehensive Heterocyclic Chemistry
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Donelly, D.M.X.1
Meegan, M.J.2
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84943376011
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Synthesis of five-membered rings with one heteroatom
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Katritzky, A. R., Ed.; Pergamon: New York
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(c) Bird, C. W.; Cheeseman, G. W. H. Synthesis of Five-membered Rings with One Heteroatom. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Ed.; Pergamon: New York, 1984; Vol. 4, pp 89-153.
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Bird, C.W.1
Cheeseman, G.W.H.2
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For recent reviews on the synthesis of benzo[b]furans, see: (a) Hou, X.-L.; Yang, Z.; Wong, H. N. C. Prog. Heterocycl. Chem. 2003, 15, 167-205.
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Prog. Heterocycl. Chem.
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Hou, X.-L.1
Yang, Z.2
Wong, H.N.C.3
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7
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For recent, selected examples on the synthesis of benzo[b]furans, see: (a) Kraus, G. A.; Kim, I. Org. Lett. 2003, 5, 1191-1192.
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Org. Lett.
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Kraus, G.A.1
Kim, I.2
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(b) Kraus, G. A.; Zhang, N.; Verkade, J. G.; Nagarajan, M.; Kisanga, P. B. Org. Lett. 2000, 2, 2409-2410.
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Kraus, G.A.1
Zhang, N.2
Verkade, J.G.3
Nagarajan, M.4
Kisanga, P.B.5
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0037142332
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(e) Wallez, V.; Durieux-Poissonnier, S.; Chavatte, P.; Boutin, J. A.; Audinot, V.; Nicolas, J.-P.; Bennejean, C.; Delagrange, P.; Renard, P.; Lesieur, D. J. Med. Chem. 2002, 45, 2788-2800.
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Wallez, V.1
Durieux-Poissonnier, S.2
Chavatte, P.3
Boutin, J.A.4
Audinot, V.5
Nicolas, J.-P.6
Bennejean, C.7
Delagrange, P.8
Renard, P.9
Lesieur, D.10
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12
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0037462376
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(f) Macleod, C.; McKiernan, G. J.; Guthrie, E. J.; Farrugia, L. J.; Hamprecht, D. W.; Macritchie, J.; Hartley, R. C. J. Org. Chem. 2003, 68, 387-401.
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Macleod, C.1
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Guthrie, E.J.3
Farrugia, L.J.4
Hamprecht, D.W.5
Macritchie, J.6
Hartley, R.C.7
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(g) Inoue, M.; Carson, M. W.; Frontier, A. J.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 1878-1889.
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Inoue, M.1
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Frontier, A.J.3
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(h) Katritzky, A. R.; Ji, Y.; Fang, Y.; Prakash, I. J. Org. Chem. 2001, 66, 5613-5615.
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(j) Thielges, S.; Meddah, E.; Bisseret, P.; Eustache, J. Tetrahedron Lett. 2004, 45, 907-910.
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(m) Atsushi Sakai, A.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1999, 40, 4211-4214.
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Atsushi Sakai, A.1
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(n) Roshchin, A. I.; Kel'chevski, S. M.; Bumagin, N. A. J. Organomet. Chem. 1998, 560, 163-167.
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Roshchin, A.I.1
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Bumagin, N.A.3
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21
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0029855494
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Formation of dihydrobenzofuran by palladium-catalyzed ether formation was reported: (a) Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 10333-10334.
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(b) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553-5566.
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(c) Kuwabe, S.-I.; Torraca, K. E.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 12202-12206.
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Kuwabe, S.-I.1
Torraca, K.E.2
Buchwald, S.L.3
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25
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0032720602
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Conversion of 1,2-dibromoarene and acetophenones to benzo[b]-furan via in situ palladium-catalyzed arylation followed by ring closure was reported: (a) Terao, Y.; Satoh, T.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1999, 72, 2345-2350.
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Bull. Chem. Soc. Jpn.
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Terao, Y.1
Satoh, T.2
Miura, M.3
Nomura, M.4
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0037471492
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(b) Veeramaneni, V. R.; Pal, M.; Yeleswarapu, K. R. Tetrahedron 2003, 59, 3283-3290.
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Tetrahedron
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Veeramaneni, V.R.1
Pal, M.2
Yeleswarapu, K.R.3
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27
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11444270393
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(c) Recently, a Pd-catalyzed intramolecular O-arylation of enolates was disclosed: Willis, M. C.; Taylor, D.; Gillmore A. T. Org. Lett. 2004, 6, 4755-57.
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Org. Lett.
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Willis, M.C.1
Taylor, D.2
Gillmore, A.T.3
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28
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0142089062
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For leading references in the synthesis of indole, see: (a) Balme, G.; Bouyssi, D.; Lomberget, T.; Monteiro, N. Synthesis 2003, 2115-2134.
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Synthesis
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Balme, G.1
Bouyssi, D.2
Lomberget, T.3
Monteiro, N.4
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33
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0041794891
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These substrates can be easily accessed via either the Friedel-Crafts acylation of the 2-halo phenyl acetyl chloride or alkylation/acylation of the 2-halo ketones/esters. See: (a) Friedel, C.; Crafts, J. M. C. R. Hebd. Seances Acad. Sci. 1877, 84, 1392, 1450.
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C. R. Hebd. Seances Acad. Sci.
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Friedel, C.1
Crafts, J.M.2
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0037451428
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(b) Desage-El, M. M.; Nowczyk, S.; Le Gall, T.; Mioskowski, C.; Amekraz, B.; Moulin, C. Angew. Chem., Int. Ed. 2003, 42, 1289-1293.
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Desage-El, M.M.1
Nowczyk, S.2
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Mioskowski, C.4
Amekraz, B.5
Moulin, C.6
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35
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0033708897
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(c) Shimizu, S.; Suzuki, T.; Sasaki, Y.; Hirai, C. Synlett 2000, 11, 1664-1666.
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Synlett
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Shimizu, S.1
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Sasaki, Y.3
Hirai, C.4
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36
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33645173287
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note
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Supporting Information.
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37
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2942538871
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For a recent example on a highly effective synthetic method for substituted 2-arylbenzofurans using [3,3]-sigmatropic rearrangement, see: Miyata, O.; Takeda, N.; Naito, T. Org. Lett. 2004, 6, 1761-1763.
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Org. Lett.
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Miyata, O.1
Takeda, N.2
Naito, T.3
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38
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0029042650
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Compound 16 was also prepared via the palladium-catalyzed annulation between iodophenol and acetelyne in 69% yield with formation of its regiosiomer in 32% yield, see: Larock, R. C.; Yum, E. K.; Doty, M. J.; Sham, K. K. C. J. Org. Chem. 1995, 60, 3270-3271.
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J. Org. Chem.
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Larock, R.C.1
Yum, E.K.2
Doty, M.J.3
Sham, K.K.C.4
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39
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33645189732
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note
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Compound 21 was prepared from the DIBAL-H reduction of the corresponding nitrile in toluene at ambient temperature in 90% yield.
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40
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0037239899
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1 reaction, see: Rossi, R. A.; Pierini, A. B.; Peñéñory, A. B. Chem. Rev. 2003, 103, 71-168.
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Chem. Rev.
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Rossi, R.A.1
Pierini, A.B.2
Peñéñory, A.B.3
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41
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0035813439
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Yoshizawa, K.; Toyota, S.; Toda, F. Tetrahedron Lett. 2001, 42, 7983-7985.
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Tetrahedron Lett.
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Yoshizawa, K.1
Toyota, S.2
Toda, F.3
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