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1
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84943407995
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Pyrazoles and their Benzo Derivatives
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For reviews, see:, Katritzky, A. R, Rees, C. W, Eds, Pergamon Press: Oxford
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(a) For reviews, see: Elguero, J. Pyrazoles and their Benzo Derivatives, In Comprehensive Heterocyclic Chemistry, Vol. 5; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: Oxford, 1984, 167-303.
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Comprehensive Heterocyclic Chemistry
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Elguero, J.1
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2
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0003593749
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Wiley, R. H, Ed, Wiley Int, New York
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(b) Behr, L. C.; Fusco, R.; Jacobe, C. H. In Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings; Wiley, R. H., Ed.; Wiley Int.: New York, 1969.
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(1969)
Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings
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Behr, L.C.1
Fusco, R.2
Jacobe, C.H.3
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3
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85083124914
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Minkin, V. 1.; Glukhovtsev, M. N.; Simkin, B. Y. Aromaticity and Antiaromaticity, Electronic and Structural Aspects; Wiley: New York, 1994.
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(c) Minkin, V. 1.; Glukhovtsev, M. N.; Simkin, B. Y. Aromaticity and Antiaromaticity, Electronic and Structural Aspects; Wiley: New York, 1994.
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4
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33745384809
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As recent examples, see: a
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As recent examples, see: (a) Hartinger, C. G.; Zorbas-Seifired, S.; Jakupec, M. A.; Kynast, B.; Zorbas, H.; Keppler, B. K. J. lnorg. Biochem. 2006, 100, 891.
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(2006)
J. lnorg. Biochem
, vol.100
, pp. 891
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Hartinger, C.G.1
Zorbas-Seifired, S.2
Jakupec, M.A.3
Kynast, B.4
Zorbas, H.5
Keppler, B.K.6
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5
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33645008215
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(b) Carella, A.; Vives, G.; Cox, T.; Jaud, J.; Rapenne, G.; Launay, J. Eur. J. lnorg. Chem. 2006, 980.
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(2006)
Eur. J. lnorg. Chem
, pp. 980
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Carella, A.1
Vives, G.2
Cox, T.3
Jaud, J.4
Rapenne, G.5
Launay, J.6
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6
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2342485135
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As examples, see: a
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As examples, see: (a)Tanitame, A.;Oyamada, Y.; Ofuji, K.; Kyoya, Y.; Suzuki, K.; Ito, H.; Kawasaki, M.; Nagai, K.; Wachi, M.; Yamagishi, J. I. Bioorg. Med. Chem. 2004, 14, 2857.
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(2004)
Bioorg. Med. Chem
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Tanitame, A.1
Oyamada, Y.2
Ofuji, K.3
Kyoya, Y.4
Suzuki, K.5
Ito, H.6
Kawasaki, M.7
Nagai, K.8
Wachi, M.9
Yamagishi, J.I.10
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7
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85083145037
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in press
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(b) Iwakubo, M.; Takami, A.; Okada, Y.; Kawata, T.; Tagami, Y.; Ohashi, H.; Sato, M.; Sugiyama, T.; Fukushima, K.; Iijima, H. Bioorg. Med. Chem. 2007, in press.
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(2007)
Bioorg. Med. Chem
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Iwakubo, M.1
Takami, A.2
Okada, Y.3
Kawata, T.4
Tagami, Y.5
Ohashi, H.6
Sato, M.7
Sugiyama, T.8
Fukushima, K.9
Iijima, H.10
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8
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13944255737
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(c) De Angelis, M.; Stossi, F.; Carlson, K. A.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. J. Med. Chem. 2005, 48, 1132.
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(2005)
J. Med. Chem
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, pp. 1132
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De Angelis, M.1
Stossi, F.2
Carlson, K.A.3
Katzenellenbogen, B.S.4
Katzenellenbogen, J.A.5
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9
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33750011410
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Lukin, K.; Hsu, M. C.; Fernando, D.; Leanna, M. R. J. Org. Chem. 2006, 71, 8166.
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(2006)
J. Org. Chem
, vol.71
, pp. 8166
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Lukin, K.1
Hsu, M.C.2
Fernando, D.3
Leanna, M.R.4
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10
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0034684496
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(a) Collot, V.; Bovy, R. B.; Rault, S. Tetrahedron Lett. 2001, 41, 9053.
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(2001)
Tetrahedron Lett
, vol.41
, pp. 9053
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Collot, V.1
Bovy, R.B.2
Rault, S.3
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11
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0033612127
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(b) Collot, V.; Dallemagne, P.; Bovy, R. B.; Rault, S. Tetrahedron 1999, 55, 6917.
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(1999)
Tetrahedron
, vol.55
, pp. 6917
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Collot, V.1
Dallemagne, P.2
Bovy, R.B.3
Rault, S.4
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12
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23244451883
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(a) El Kazzouli, S.; Bouissane, L.; Khouili, M.; Guillaumet, G. Tetrahedron Lett. 2005, 46, 6163.
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(2005)
Tetrahedron Lett
, vol.46
, pp. 6163
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El Kazzouli, S.1
Bouissane, L.2
Khouili, M.3
Guillaumet, G.4
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13
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22544486271
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(b) Bouissane, L.; El Kazzouli, S.; Léger, J. M.; Jarry, C.; Rakib, E. M.; Khouili, M.; Guillaumet, G. Tetrahedron 2005, 61, 8218.
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(2005)
Tetrahedron
, vol.61
, pp. 8218
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Bouissane, L.1
El Kazzouli, S.2
Léger, J.M.3
Jarry, C.4
Rakib, E.M.5
Khouili, M.6
Guillaumet, G.7
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14
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30344440110
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(c) Bouissane, L.; El Kazzouli, S.; Léonce, S.; Pfeiffer, B.; Rakib, E. M.; Khouili, M.; Guillaumet, G. Bioorg. Med. Chem. 2006, 14, 1078.
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(2006)
Bioorg. Med. Chem
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Bouissane, L.1
El Kazzouli, S.2
Léonce, S.3
Pfeiffer, B.4
Rakib, E.M.5
Khouili, M.6
Guillaumet, G.7
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15
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0035856516
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Raman, C. S.; Li, H.; Martasek, P.; Southan, G.; Masters, B. S.; Poulos, T. L. Biochemistiy 2001, 40, 13448.
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(2001)
Biochemistiy
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Raman, C.S.1
Li, H.2
Martasek, P.3
Southan, G.4
Masters, B.S.5
Poulos, T.L.6
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16
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0035821414
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Schumann, P.; Collot, V.; Hommet, Y.; Gsell, W.; Dauphin, F.; Sopkova, J.; MacKenzie, E. T.; Duval, D.; Boulouard, M.; Rault, S. Bioorg. Med. Chem. Lett. 2001, 77, 1153.
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(2001)
Bioorg. Med. Chem. Lett
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Schumann, P.1
Collot, V.2
Hommet, Y.3
Gsell, W.4
Dauphin, F.5
Sopkova, J.6
MacKenzie, E.T.7
Duval, D.8
Boulouard, M.9
Rault, S.10
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17
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85083138180
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For 3: mp 94°C. MS (CI-CH4, mlz, 267 [M, H, HRMS: mlz [M, NR4, calcd for C8H5N2F3O3S: 326.0422; found: 326.0424. 1H NMR (200 MHz, acetone-d6, δ, 8.27 (s, 1 H, 7.93 (2 x d, J, 9.2 Hz, 2 H, 7.50 (s, 1 H, 7.27 (t, J, 9.2 Hz, 1 H, 19F NMR (188 MHz, acetone-d6, δ, 68.92 (s, 13C NMR 75 MHz, acetone-d6, δ, 128.4, 122.9, 122.5, 121.8, 119.4, 119.0. 115.8, 116.5
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6): δ = 128.4, 122.9, 122.5, 121.8, 119.4, 119.0. 115.8, 116.5.
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20
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85083130988
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Comins, D. L.; Dehghani, A.; Foti, C. J.; Joseph, S. P. Org. Synth. 1998, Coll. IX, 165.
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(b) Comins, D. L.; Dehghani, A.; Foti, C. J.; Joseph, S. P. Org. Synth. 1998, Coll. Vol. IX, 165.
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21
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85083120392
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Porter, H. D.; Peterson, W. D. Org. Synth. 1955, Coll. III, 660.
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(a) Porter, H. D.; Peterson, W. D. Org. Synth. 1955, Coll. Vol. III, 660.
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24
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37049093320
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(d) Suzuki, N.; Kaneko, Y.; Nomoto, T.; Isawa, Y. Chem. Commun. 1984, 1523.
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(1984)
Chem. Commun
, pp. 1523
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Suzuki, N.1
Kaneko, Y.2
Nomoto, T.3
Isawa, Y.4
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25
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0000249893
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(e) Doyle, M. P.; Siegfried, B.; Elliot, R. C.; Dellaria, J. F. J. Org. Chem. 1977, 42, 2431.
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(1977)
J. Org. Chem
, vol.42
, pp. 2431
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Doyle, M.P.1
Siegfried, B.2
Elliot, R.C.3
Dellaria, J.F.4
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26
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85083135629
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3): δ = 142.4, 136.3, 135.6, 123.2, 122.7, 121.0, 115.7.
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3): δ = 142.4, 136.3, 135.6, 123.2, 122.7, 121.0, 115.7.
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27
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85083121420
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2O and dried to afford 7-nitro-1 H-indazole (5.29 g, 98% yield); mp 180°C.
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2O and dried to afford 7-nitro-1 H-indazole (5.29 g, 98% yield); mp 180°C.
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29
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0003441482
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Wiley, R. H, Ed, Wiley Int, New York
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st Century; Wiley, R. H., Ed.; Wiley Int.: New York, 2004.
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(2004)
st Century
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Tsuji, J.1
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30
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0032514998
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(a) Anderson, B. A.; Bell, E. C.; Ginah, F. O.; Harn, N. K.; Pagh, L. M.; Wepsiec, J. P. J. Org. Chem. 1998, 63, 8224.
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(1998)
J. Org. Chem
, vol.63
, pp. 8224
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Anderson, B.A.1
Bell, E.C.2
Ginah, F.O.3
Harn, N.K.4
Pagh, L.M.5
Wepsiec, J.P.6
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31
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0038669308
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(b) Sundermeier, M.; Zapf, A.; Mutyala, S.; Baumann, W.; Sans, J.; Weiss, S.; Beller, M. Chem. Eur. J. 2003, 9, 1828.
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(2003)
Chem. Eur. J
, vol.9
, pp. 1828
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Sundermeier, M.1
Zapf, A.2
Mutyala, S.3
Baumann, W.4
Sans, J.5
Weiss, S.6
Beller, M.7
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33
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0742286896
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Kumar, K.; Zapf, A.; Michalik, D.; Tillac, A.; Heinrich, T.; Böttcher, H.; Arlt, M.; Beller, M. Org. Lett. 2004, 6, 7.
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(2004)
Org. Lett
, vol.6
, pp. 7
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Kumar, K.1
Zapf, A.2
Michalik, D.3
Tillac, A.4
Heinrich, T.5
Böttcher, H.6
Arlt, M.7
Beller, M.8
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35
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85083129780
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(b) Elguero, J.; Fruchier, A.; Jacquier, R. Bull. Soc. Chim. Fr. 1966, 9, 3401.
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(1966)
Bull. Soc. Chim. Fr
, vol.9
, pp. 3401
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Elguero, J.1
Fruchier, A.2
Jacquier, R.3
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38
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0141954371
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(b) Frantz, D. E.; Weaver, D. G.; Carey, J. P.; Kress, M. H.; Dolling, U. H. Org. Lett. 2002, 4, 4717.
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(2002)
Org. Lett
, vol.4
, pp. 4717
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Frantz, D.E.1
Weaver, D.G.2
Carey, J.P.3
Kress, M.H.4
Dolling, U.H.5
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40
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85083125660
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6): δ = 136.2, 132.8, 135.5, 127.5, 125.2, 121.5, 116.9, 94.9.
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6): δ = 136.2, 132.8, 135.5, 127.5, 125.2, 121.5, 116.9, 94.9.
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41
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0008627511
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Lazaro, R.; Bouchet, P.; Elguero, J. ACH Models Chem. 1999, 136, 497.
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(1999)
ACH Models Chem
, vol.136
, pp. 497
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Lazaro, R.1
Bouchet, P.2
Elguero, J.3
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42
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85083122528
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For 12: mp 77.5°C. MS (EI, m/z, 142 [M, HRMS (TOF-MS, ES, mlz [M, H, calcd for C 9H7N2: 143.0609; found: 143.0620. 1H NMR (200 MHz, CDCl3, δ =10.70 (br s, 1 H, 8.15 (s, 1 H, 7.78, 7.56(2 x d, J, 8.1 Hz, 2 H, 7.15 (t, J, 8.1 Hz, 1 H, 3.46 (s, 1 H, 13C NMR (75 MHz, CDCl3, δ, 134.0, 130.8, 122.8, 122.2, 122.1, 121.1, 104.5, 82.5, 79.2. For 5: mp 160.9°C. MS (EI, mlz, 323 [M, 243 [M, Br, 116 [M, Br, Anal. Calcd for C7H4N 2IBr: C, 26.01; H, 1.24; N, 8.67. Found: C, 26.23; H, 1.28; N, 8.61. 1H NMR (200 MHz;1CDCl3, δ =10.10 (br s, 1 H, 7.81, 7.63 (2 x d, J, 8.0 Hz, 2 H, 7.03 t, J, 8.0 Hz, 1 H
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3): δ = 143.1, 136.67, 131.12, 124.26, 123.46, 120.43, 112.20.
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43
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0036006408
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For examples, see: a
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For examples, see: (a) Chapman, G. M.; Stanforth, S. P.; Tarbit, B.; Watson, M. D. J. Chem. Soc., Perkin Trans. 1 2002, 581.
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(2002)
J. Chem. Soc., Perkin Trans. 1
, pp. 581
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Chapman, G.M.1
Stanforth, S.P.2
Tarbit, B.3
Watson, M.D.4
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44
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0002475963
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(b) Tao, W.; Nesbitt, S.; Heck, R. F. J. Org. Chem. 1990, 55, 63.
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(1990)
J. Org. Chem
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Tao, W.1
Nesbitt, S.2
Heck, R.F.3
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