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Bernini, R.; Cacchi, S.; Fabrizi, G.; Filisti, E.; Sferrazza, A. Synlett 2009, submitted.
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67649309829
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note
-
Conjugate additions of 2-(alkynyl)anilines to 1,3-diphenylpropynones (MeOH, 120°C) were carried out using a Carousel Tube Reaction (Radley Discovery).
-
-
-
-
13
-
-
67649368423
-
-
note
-
Enaminones 3 can also be prepared by treating the conjugate addition products derived from 2-iodonilines and 1,3-diarylpropynones with terminal alkynes. Using this procedure, 3a, 3q, and 3r were isolated in 77%, 74%, and 70% overall yields, respectively. This protocol, however, appeared less suited for the development of a sequential process that would omit the isolation of the enaminone intermediates (Scheme 4). (Chemical Equation Presented)
-
-
-
-
14
-
-
0001628407
-
-
For some selected references on the transition-metal-catalyzed cyclization of 2-(alkynyl)anilines and -anilides, see: (Pd and Au)
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For some selected references on the transition-metal-catalyzed cyclization of 2-(alkynyl)anilines and -anilides, see: (a) (Pd and Au) Iritani, K.; Matsubara, S.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1799.
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Iritani, K.1
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15
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0242712817
-
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While the manuscript was in preparation, an indium-catalyzed cyclization of β-enamino esters [prepared from β-keto esters and 2-(alkynyl)anilines] to N-vinylic indoles was described
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(b) (Cu) Cacchi, S.; Fabrizi, G.; Parisi, L. M. Org. Lett. 2003, 5, 3843.
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64549091509
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While the manuscript was in preparation, an indium-catalyzed cyclization of β-enamino esters [prepared from β-keto esters and 2-(alkynyl)anilines] to N-vinylic indoles was described:
-
While the manuscript was in preparation, an indium-catalyzed cyclization of β-enamino esters [prepared from β-keto esters and 2-(alkynyl)anilines] to N-vinylic indoles was described: (c) Murai, K.; Hayashi, S.; Takaichi, N.; Kita, Y.; Fujioka, H. J. Org. Chem. 2009, 74, 1418.
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0000037321
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(a) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L.; Pace, P. Synlett 1997, 1363.
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Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 2000, 647.
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Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 1993, 65.
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Arcadi, A.; Cacchi, S.; Fabrizi, G.; Manna, F.; Pace, P. Synlett 1998, 446.
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Arcadi, A.1
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22
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67649368422
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note
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21NO:C, 87.19; H, 5.30. Found: C, 87.25; H, 5.36.
-
-
-
-
23
-
-
67649323759
-
-
note
-
2: C, 77.66; H, 4.78. Found: C, 77.52; H, 4.70.
-
-
-
-
24
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-
11844282171
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