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Duggan, M. D.; Duong, L. T.; Fisher, J. E.; Hamill, T. G.; Hoffman, W. F.; Huff, J. R.; Ihle, N. C.; Leu, C.-T.; Nagy, R. M.; Perkins, J. J.; Rodan, S. B.; Wesolowski, G.; Whitman, D. B.; Zartman, A. E.; Rodan, G. A.; Hartman, G. D. J. Med. Chem. 2000, 43, 3736.
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6
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18644384406
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Brashear, K. M.; Hunt, C. A.; Kucer, B. T.; Duggan, M. E.; Hartman, G. D.; Rodan, G. A.; Rodan, S. B.; Leu, C.-T.; Prueksaritanont, T.; Fernandez-Metzler, C.; Barrish, A.; Homnick, C. F.; Hutchinson, J. H.; Coleman, P. J. Bioorg. Med. Chem. Lett. 2002, 3483.
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7
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Preparation of 2 via a Chichibabin cyclization has been reported. Palucki, M.; Hughes, D. L.; Yasuda, N. Y.; Yang, C.; Reider, P. J. Tetrahedron Lett. 2001, 42, 6811.
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8
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1642316701
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Katritzky, A. R., Ed.; The Pergamon Press: Oxford, England, Chapter 2.11
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Lowe, P. A. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Ed.; The Pergamon Press: Oxford, England, 1984; Vol. 2, Chapter 2.11.
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Lowe, P.A.1
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9
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1642418759
-
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Rivera, N.R.1
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Yasuda, N.6
Hughes, D.L.7
-
10
-
-
0037462413
-
-
A highly selective Friedländer has recently been reported: Dormer, P. G.; Eng, K. K.; Farr, R. N.; Humphrey, G. R.; McWilliams, J. C.; Reider, P. J.; Sager, J. W.; Volante, R. P. J. Org. Chem. 2003, 68, 467.
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Reider, P.J.6
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11
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0003151465
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The Friedlander Synthesis of Quinolines
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Daube, W. C., Ed.; J. Wiley & Sons: New York
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Cheng, C.-C.1
Yan, S.-J.2
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12
-
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0033515462
-
-
Ammonium hydroxide was used as a solvent to prevent the formation of the corresponding dimer secondary amine. For an example, see: Journet, M.; Cai, D.; DiMichele, L. M.; Hughes, D. L.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1999, 64, 2411.
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Journet, M.1
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Hughes, D.L.4
Larsen, R.D.5
Verhoeven, T.R.6
Reider, P.J.7
-
13
-
-
1642345869
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-
note
-
Reduction of 13(Z) is not as clean as that of 13(E).
-
-
-
-
14
-
-
0035912306
-
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and references therein
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Hsiao, Y.; Rivera, N. R.; Yasuda, N.; Hughes, D. L.; Reider, P. J. Org. Lett. 2000, 3, 1101 and references therein.
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Hsiao, Y.1
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Reider, P.J.5
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33845551642
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Flynn, D. L.; Zelle, R. E.; Grieco, P. A. J. Org. Chem. 1983, 48, 2424.
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Flynn, D.L.1
Zelle, R.E.2
Grieco, P.A.3
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16
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0037195481
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Analytical method development for this reaction: Buote, A.; Kelly, J.; Hsiao, Y.; Yasuda, N.; Antonucci, V. J. Chromat. A 2002, 978, 177.
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Antonucci, V.J.5
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17
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46149129231
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Teulade reported that this anion is stable at 0 °C for 5 min prior to dimerization. We could not repeat these data. Teulade, M.-P.; Savignac, P. J. Organomet. Chem. 1986, 312, 283.
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0030952575
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Butora, G.; Reed, J. W.; Hudlicky, T.; Brammer, L. E. J.; Higgs, P. I.; Simmons, D. P.; Heard, N. E. J. Am. Chem. Soc. 1997, 119, 7694.
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Simmons, D.P.6
Heard, N.E.7
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20
-
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1642357206
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-
note
-
Distillation residue from this reaction has an exothermic nature (initiation temperature = 74.2 °C; maximum temperature of the exothermic reaction = 386.1 °C; maximum rate of temperature increase = 1104.6 °C/min).
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-
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22
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0000620586
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Boucher, É.; Simard, M.; Wuest, J. D. J. Org. Chem. 1995, 60, 1408.
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23
-
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1642383340
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-
note
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Heat of reaction of this reaction as measured using an RC-1 reaction apparatus is -48.8 Kcal.
-
-
-
-
24
-
-
1642358811
-
-
note
-
The corresponding p-nitrophenylcarbamate is extremely unreactive. No reaction was observed in the presence of excess benzylamine even at elevated temperature.
-
-
-
-
25
-
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0028085353
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2 has been reported. Wong, W. C.; Wang, D.; Forray, C.; Vaysse, P. J.-J.; Branchek, T. A.; Gluchowki, C. Bioorg. Med. Chem. Lett. 1994, 4, 2317.
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26
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0013966011
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Wright, W. B. J.; Brabander, H. J.; Hardy, R. A. J. J. Med. Chem. 1966, 9, 858.
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27
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0029899187
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For review: Cotarca, L.; Delogu, P.; Nardelli, A.; Šunjić, V. Synthesis 1996, 553.
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Cotarca, L.1
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28
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0000597733
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For other synthesis and physical data: Giovannini, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1989, 54, 228.
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Giovannini, A.1
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29
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1642344222
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Similar ring opening was reported: Lieb, F. DE Patent 27 11 010, 1978
-
Similar ring opening was reported: Lieb, F. DE Patent 27 11 010, 1978.
-
-
-
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30
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1642363749
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note
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Trademark by Mitsubishi Chemical.
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