Solid-phase synthesis of heterocycles via palladium-catalyzed annulation

Tetrahedron Letters

Volumn 39, Issue 52, 1998, Pages 9605-9608

  Wang, Yao ^a   Huang, Tai Nang ^a,b  

^a HOFFMANN LA ROCHE INC   (United States)

^b SHIONOGI AND CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ANILINE DERIVATIVE; BENZOFURAN DERIVATIVE; BENZOPYRAN DERIVATIVE; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; PALLADIUM; PHENOL DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; SYNTHESIS;

EID: 0032564639     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02337-5     Document Type: Article

References (21)

1. 2. (a) Kim, W.-G.; Kim, J.-P.; Koshino, H.; Shin-Ya, K.; Seto, H.; Yoo, L-D. Tetrahedron 1997, 53, 4309.
2. (b) Bonjoch, J; Sole, D.; Bosch, J. J. Am. Chem. Soc. 1993, 115, 2064.
3. 3. (a) Kohno, Y.; Awano, K.; Miyashita, M.; Ishizaki, T.; Kuriyama, K.; Sakoe, Y.; Kudoh, S.; Saito, K.; Koji, E. Bioorg. Med. Chem. Lett. 1997, 7, 1519.
4. (b) Katritzky, A. R.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52, 15031.
5. 4. (a) Snider, B. B.; Han, L.; Xie, C. J. Org. Chem. 1997, 62, 6978.
6. (b) Pfefferle, W.; Anke, H.; Bross, M.; Steffan, B.; Vianden, R.; Steglich, W. J. Antibiot. 1990, 43, 648.
7. 5. (a) Krohn, K.; Michel, A.; Bahramsari, R.; Floerke, U.; Aust, H. J.; Draeger, S.; Schulz, B.; Wray, V. Nat. Prod. Lett. 1996, 8, 43.
8. (b) Hepworth, J. D.; Heron, B. M. Prog. Heterocycl. Chem. 1995, 7, 268.
9. 6. (a) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1995, 60, 482.
10. (b) Larock, R. C.; Berrios-Pena, N. G.; Fried, C. A. J. Org. Chem. 1991, 56, 2615.
11. 7. (a) Larock, R. C.; Guo, L. Synlett 1995, 465.
12. (b) Larock, R. C.; Berrios-Pena, N. G.; Narayanan, K. J. Org. Chem. 1990, 55, 3447.
13. 8. Larock, R. C.; Berrios-Pena, N. G.; Fried, C. A.; Yum, E. K.; Tu, C.; Leong, W. J. Org. Chem. 1993, 58, 4509.
14. 9. (a) Larock, R. C.; Yum, E. K.; Doty, M. J.; Sham, K. K. C. J. Org. Chem. 1995, 60, 3270.
15. (b) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689.
16. 10. Solid-phase synthesis of tetrahydroquinolines via three component condensation was reported after the completion of the manuscript: (a) Kiselyov, A. S., Smith, L.; Armstrong, R. W. Tetrahedron 1998, 54, 5089.
17. (b) Kiselyov, A. S.; Smith, L.; Virgilio, A.; Armstrong, R. W. Tetrahedron 1998, 54, 7987.
18. 11. Rink, H. Tetrahedron Lett. 1987, 28, 3787.
19. 12. Sy, W.-W. Synth. Commun. 1992, 22, 3215.
20. 3) δ 0.95 (t, J = 7.5 Hz, 3 H), 2.03 (quintet, J = 7.4 Hz, 2 H), 2.38 (s, 3 H), 2.71 (dd, J= 16.6, 3.2 Hz, 1 H), 3.10 (dd, J= 16.3, 10.0 Hz, 1 H), 4.82 (m, 1 H), 5.43 (ddt, J = 15.3, 7.3, 1.5 Hz, 1 H), 5.84 (dt, J = 15.3, 6.3 Hz, 1 H), 6.19 (br s, 2 H), 7.21 (d, J = 8.2 Hz, 2 H), 7.59-7.66 (m, 5 H).
21. 14. Edgar, K. J.; Falling, S. N. J. Org. Chem. 1990, 55, 5287.