Synthesis of polysubstituted quinolines from the acetates of Baylis-Hillman adducts: Aza-Claisen rearrangement as the key step

Bulletin of the Korean Chemical Society

Volumn 26, Issue 6, 2005, Pages 1001-1004

  Seung, Chan Kim ^a   Gowrisankar, Saravanan ^a   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

Author keywords

Aza Claisen rearrangement; Baylis Hillman adducts; PPA; Quinolines

Indexed keywords

EID: 22744450779     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2005.26.6.1001     Document Type: Article

References (24)

1. For our recent papers on the reaction of Baylis-Hillman adducts bearing aniline moiety, see (a) Lee, C. G.; Lee, K. Y.; Lee, S.; Kim, J. N. Tetrahedron 2005, 61, 1493.
2. (b) Lee, C. G.; Lee, K. Y.; Gowrisankar, S.; Kim, J. N. Tetrahedron Lett. 2004, 45, 7409.
3. For our recent publications on the synthesis of quinoline derivatives, see (a) Lee, K. Y.; Kim, J. M.; Kim, J. N. Tetrahedron 2003, 59, 385.
4. (b) Kim, J. N.; Chung, Y. M.; Im, Y. J. Tetrahedron Lett. 2002, 43, 6209.
5. (c) Kim, J. N.; Kim, H. S.; Gong, J. H.; Chung, Y. M. Tetrahedron Lett. 2001, 42, 8341.
6. (d) Kim, J. N.; Lee, H. J.; Lee, K. Y.; Kim, H. S. Tetrahedron Lett. 2001, 42, 3737.
7. (e) Kim, J. N.; Lee, K. Y.; Kim, H. S.; Kim, T. Y. Org. Lett. 2000, 2, 343.
8. (f) Gowrisankar, S.; Na, J. E.; Lee, M. J.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 319.
9. (g) Lee, K. Y.; Kim, J. M.; Kim, J. N. Bull. Korean Chem. Soc. 2002, 23, 1493.
10. (h) Lee, K. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2002, 23, 939.
11. (i) Na, J. E.; Lee, K. Y.; Park, D. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 323 and further references for the synthesis of polysubstituted quinolines cited therein.
12. For the introduction of nucleophiles at the secondary position of the Baylis-Hillman adducts by using the corresponding DABCO salt, see (a) Kim, J. M.; Lee, K. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2004, 25, 328.
13. (b) Lee, K. Y.; Kim, T. H.; Kim, J. N. Bull. Korean Chem. Soc. 2004, 25, 1966 and further references cited therein.
14. For the synthesis of Baylis-Hillman adducts bearing the aniline moiety, see (a) Rajesh, S.; Banerji, B.; Iqbal, J. J. Org. Chem. 2002, 67, 7852.
15. (b) Bauchat, P.; Le Rouille, E.; Foucaud, A. Bull. Chim. Soc. Fr. 1991, 267.
16. (c) Buchholz, R.; Hoffmann, H. M. R. Helv. Chim. Acta 1991, 74, 1213.
17. For the acetates of Baylis-Hillman adducts of ethyl acrylate (Scheme 1), we could not observe the formation of cinnamyl amine derivatives during the preparation of the corresponding secondary adducts.
18. (a) Castro, A. M. M. Chem. Rev. 2004, 104, 2939 and further references cited therein.
19. (b) Jolidon, S.; Hansen, H.-J. Helv. Chim. Acta 1977, 60, 978.
20. (c) Anderson, W. K.; Lai, G. Synthesis 1995, 1287.
21. (a) Cho, C. S.; Kim, B. T.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2001, 2576.
22. (b) Cho, C. S.; Kim, B. T.; Choi, H.-J.; Kim, T.-J.; Shim, S. C. Tetrahedron 2003, 59, 7997.
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24. (d) Abbiati, G; Beccalli, E. M.; Broggini, G; Zoni, C. Tetrahedron 2003, 59, 9887.