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34548770580
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(b) Gabriele, B.; Mancuso, R.; Salerno, G.; Ruffolo, G.; Plastina, P. J. Org. Chem. 2007, 72, 6873, and references cited therein.
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For recent examples of synthesis of indoles, see: a
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For recent examples of synthesis of indoles, see: (a) Cui, S.-L.; Wang, J.; Wang, Y.-G. J. Am. Chem. Soc. 2008, 130, 13526.
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34547947084
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Morikawa, S.; Yamazaki, S.; Tsukada, M.; Izuhara, S.; Morimoto, T.; Kakiuchi, K. J. Org. Chem. 2007, 72, 6459.
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Moriyama, K.5
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28
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67649569805
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2 gave 4′-aminoacetophenone in 47% isolated yield. On the other hand, the reaction of (trimethylsilylethynyl)benzene did not change under the reaction conditions. The detailed mechanism of loss of TMS is under investigation.
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2 gave 4′-aminoacetophenone in 47% isolated yield. On the other hand, the reaction of (trimethylsilylethynyl)benzene did not change under the reaction conditions. The detailed mechanism of loss of TMS is under investigation.
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29
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67649546700
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2′-Aminoacetophenone 5 and the amine adduct C are possibly formed in situ from Zn-catalyzed water addition to the triple bond of 2-ethynylanilines. The effect of water in situ will be investigated in due course.
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2′-Aminoacetophenone 5 and the amine adduct C are possibly formed in situ from Zn-catalyzed water addition to the triple bond of 2-ethynylanilines. The effect of water in situ will be investigated in due course.
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0001201983
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Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1989, 30, 258.1.
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Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1989, 30, 258.1.
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0029823888
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Ezquerra, J.; Pedregal, C.; Lamas, C.; Barluenga, J.; Pérez, M.; García-Martín, M. A.; González, J. M. J. Org. Chem. 1996, 61, 5804.
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González, J.M.7
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35
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46849092817
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For a recent example of synthesis of indole-2-acetic esters, see
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For a recent example of synthesis of indole-2-acetic esters, see: Gabriele, B.; Mancuso, R.; Salerno, G.; Lupinacci, E.; Ruffolo, G.; Costa, M. J. Org. Chem. 2008, 73, 4971.
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J. Org. Chem
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Gabriele, B.1
Mancuso, R.2
Salerno, G.3
Lupinacci, E.4
Ruffolo, G.5
Costa, M.6
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36
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67649570802
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Typical experimental procedure (Table 1, Entry 4, To a solution of lb (107 mg, 0.39 mmol) in 1,2-dichloroethane (0.72 mL) was added 2-(trimethylsilylethynyl)aniline (2b, 74 mg, 0.39 mmol) and Zn(OTf) 2 (29 mg, 0.08 mmol, The mixture was heated at 80 °C and stirred for 3 h. The reaction mixture was cooled to 0 °C and quenched with water. The mixture was diluted with dichloromethane and then saturated aqueous NaHCO3 was added. The organic phase was extracted with dichloromethane, dried (Na2SO4, and evaporated in vacuo. The residue was purified by column chromatography over silica gel with hexane-ether as eluent to give 4a (76 mg, 58, 4a: Rf, 0.1 (hexane-ether, 1, 1, Colorless crystals; mp 124-125 °C; 1H NMR (400 MHz, CDCl3) δ (ppm) 1.02 (t, J, 7.1 Hz, 3H, 1.33 (t, J, 7.1 Hz, 3H, 1.98 (s, 3H, 3.77-4.05 (m, 1H, 4.07-4.15 (m, 1H, 4.35 q, J, 7.1 Hz, 2H
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6: C, 61.25; H, 5.75; N, 4.20. Found: C, 61.00; H, 5.6.1; N, 4.22.
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