Novel synthesis of fused indoles by the palladium-catalyzed cyclization of N-cycloalkenyl-o-haloanilines

Synlett

Volumn , Issue 5, 2004, Pages 907-909

  Watanabe, Takeshi ^a   Arai, Shigeru ^a   Nishida, Atsushi ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Heterocycles; Indole; Palladium; Synthesis

Indexed keywords

ALKENYL GROUP; ANILINE DERIVATIVE; CYCLOALKANE DERIVATIVE; INDOLE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CYCLIZATION; ISOMERIZATION; MOLECULAR MECHANICS; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 1942425101     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-820039     Document Type: Article

References (20)

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7. Synthesis of indoles by palladium-catalyzed cyclization of W-alkenyl-o-haloanilines, see: (a) Caddick, S.; Kofie, W. Tetrahedron Lett. 2002, 43, 9347. (b) Michael, J. P.; de Koning, C. B.; Petersen, R. L.; Stanbury, T. V. Tetrahedron Lett. 2001, 42, 7513. (c) Latham, E. J.; Stanforth, S. P. J. Chem. Soc, Perkin Trans. 1 1997, 2059. (d) Blache, Y.; Sinibaldi-Troin, M.-E.; Voldoire, A.; Chavignon, O.; Gramain, J.-C.; Teulade, J.-C.; Chapat, J.-P. J. Org. Chem. 1997, 62, 8553. (e) Chen, L. C.; Yang, S. C.; Wang, H. M. Synthesis 1995, 385. (f) Michael, J. P.; Chang, S.-F.; Wilson, C. Tetrahedron Lett. 1993, 34, 8365. (g) Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanaka, H. Synthesis 1990, 215. (h) Kasahara, A.; Izumi, T.; Murakami, S.; Yanai, H.; Takatori, M. Bull. Chem. Soc. Jpn. 1986, 59, 927. (i) Iida, H.; Yuasa, Y.; Kibayashi, C. J. Org. Chem. 1980, 45, 2938.
8. Synthesis of indoles by palladium-catalyzed cyclization of W-alkenyl-o-haloanilines, see: (a) Caddick, S.; Kofie, W. Tetrahedron Lett. 2002, 43, 9347. (b) Michael, J. P.; de Koning, C. B.; Petersen, R. L.; Stanbury, T. V. Tetrahedron Lett. 2001, 42, 7513. (c) Latham, E. J.; Stanforth, S. P. J. Chem. Soc, Perkin Trans. 1 1997, 2059. (d) Blache, Y.; Sinibaldi-Troin, M.-E.; Voldoire, A.; Chavignon, O.; Gramain, J.-C.; Teulade, J.-C.; Chapat, J.-P. J. Org. Chem. 1997, 62, 8553. (e) Chen, L. C.; Yang, S. C.; Wang, H. M. Synthesis 1995, 385. (f) Michael, J. P.; Chang, S.-F.; Wilson, C. Tetrahedron Lett. 1993, 34, 8365. (g) Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanaka, H. Synthesis 1990, 215. (h) Kasahara, A.; Izumi, T.; Murakami, S.; Yanai, H.; Takatori, M. Bull. Chem. Soc. Jpn. 1986, 59, 927. (i) Iida, H.; Yuasa, Y.; Kibayashi, C. J. Org. Chem. 1980, 45, 2938.
9. Synthesis of indoles by palladium-catalyzed cyclization of W-alkenyl-o-haloanilines, see: (a) Caddick, S.; Kofie, W. Tetrahedron Lett. 2002, 43, 9347. (b) Michael, J. P.; de Koning, C. B.; Petersen, R. L.; Stanbury, T. V. Tetrahedron Lett. 2001, 42, 7513. (c) Latham, E. J.; Stanforth, S. P. J. Chem. Soc, Perkin Trans. 1 1997, 2059. (d) Blache, Y.; Sinibaldi-Troin, M.-E.; Voldoire, A.; Chavignon, O.; Gramain, J.-C.; Teulade, J.-C.; Chapat, J.-P. J. Org. Chem. 1997, 62, 8553. (e) Chen, L. C.; Yang, S. C.; Wang, H. M. Synthesis 1995, 385. (f) Michael, J. P.; Chang, S.-F.; Wilson, C. Tetrahedron Lett. 1993, 34, 8365. (g) Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanaka, H. Synthesis 1990, 215. (h) Kasahara, A.; Izumi, T.; Murakami, S.; Yanai, H.; Takatori, M. Bull. Chem. Soc. Jpn. 1986, 59, 927. (i) Iida, H.; Yuasa, Y.; Kibayashi, C. J. Org. Chem. 1980, 45, 2938.
10. Synthesis of indoles by palladium-catalyzed cyclization of W-alkenyl-o-haloanilines, see: (a) Caddick, S.; Kofie, W. Tetrahedron Lett. 2002, 43, 9347. (b) Michael, J. P.; de Koning, C. B.; Petersen, R. L.; Stanbury, T. V. Tetrahedron Lett. 2001, 42, 7513. (c) Latham, E. J.; Stanforth, S. P. J. Chem. Soc, Perkin Trans. 1 1997, 2059. (d) Blache, Y.; Sinibaldi-Troin, M.-E.; Voldoire, A.; Chavignon, O.; Gramain, J.-C.; Teulade, J.-C.; Chapat, J.-P. J. Org. Chem. 1997, 62, 8553. (e) Chen, L. C.; Yang, S. C.; Wang, H. M. Synthesis 1995, 385. (f) Michael, J. P.; Chang, S.-F.; Wilson, C. Tetrahedron Lett. 1993, 34, 8365. (g) Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanaka, H. Synthesis 1990, 215. (h) Kasahara, A.; Izumi, T.; Murakami, S.; Yanai, H.; Takatori, M. Bull. Chem. Soc. Jpn. 1986, 59, 927. (i) Iida, H.; Yuasa, Y.; Kibayashi, C. J. Org. Chem. 1980, 45, 2938.
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20. 3): δ = 14.3, 25.8, 36.5, 39.4, 48.5, 53.7, 61.6, 111.2, 111.3, 117.6, 119.5, 121.9, 127.0, 129.2, 130.9, 132.7, 135.5, 139.1, 174.8.