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Formal carboamination through the two-component coupling reactions has been developed. See: (a) Arcadi, A. Synlett 1997, 941-943.
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Stoichiometric addition of an amide bond to alkynes was achieved by using a chromium complex. See: Rudler, H.; Parlier, A.; Bezennine-Lafollée, S.; Vaissermann, J. Eur. J. Org. Chem. 1999, 2825-2833.
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0028094766
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Acylindoles are also produced catalytically through the three-component coupling reactions using carbon monoxide. See: (a) Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803-11812.
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4344677512
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note
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The precise role of the solvent is not clear. However, we presume that the zwitterionic intermediate would be stabilized in electron-rich aromatics.
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17
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4344578215
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note
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We confirmed that deacylation from N-methylacetanilide hardly occurred under the same conditions (90% recovery, 16 h). This result clearly indicates that indoles 3 were not generated through the catalytic cyclization of 2-alkynylanilines that might be yielded via the deprotection of the starting materials.
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18
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4344708243
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note
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We confirmed that the reactions from both of these substrates proceeded simultaneously by monitoring thin-layer chromatography (TLC) and gas chromatography (GC-MS) analyses.
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(a) Cacchi, S.; Carnicelli, V.; Marinelli, F. J. Organomet. Chem. 1994, 475, 289-296.
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See also ref 3f
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(d) See also ref 3f.
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23
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2942557280
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For reviews on the transition metal-catalyzed syntheses of heteroaromatic compounds, see: (a) Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127-2198.
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See also ref 12c
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(d) See also ref 12c.
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27
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and references therein
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Recently, our group also reported catalytic constructions of highly substituted indoles. See: Kamijo, S.; Yamamoto. Y. J. Org. Chem. 2003, 68, 4764-4771 and references therein.
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