Pd-mediated synthesis of 2-arylquinolines and tetrahydropyridines from modified Baylis-Hillman adducts

Tetrahedron Letters

Volumn 49, Issue 10, 2008, Pages 1670-1673

  Gowrisankar, Saravanan ^a   Lee, Hyun Seung ^a   Kim, Jeong Mi ^a   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

Author keywords

2 Arylquinolines; Baylis Hillman adducts; Palladium; Tetrahydropyridines

Indexed keywords

2 ARYLQUINOLINE DERIVATIVE; PALLADIUM; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; TETRAHYDROPYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

EID: 38949099682     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.12.133     Document Type: Article

References (43)

1. For the Pd-mediated synthesis of hetero- and carbocyclic compounds from modified Baylis-Hillman adducts, see:. Ribiere P., Declerck V., Nedellec Y., Yadav-Bhatnagar N., Martinez J., and Lamaty F. Tetrahedron 62 (2006) 10456-10466
2. Declerck V., Ribiere P., Nedellec Y., Allouchi H., Martinez J., and Lamaty F. Eur. J. Org. Chem. (2007) 201-208
3. Szlosek-Pinaud M., Diaz P., Martinez J., and Lamaty F. Tetrahedron 63 (2007) 3340-3349
4. Vasudevan A., Tseng P.-S., and Djuric S.W. Tetrahedron Lett. 47 (2006) 8591-8593
5. Trost B.M., Thiel O.R., and Tsui H.-C. J. Am. Chem. Soc. 125 (2003) 13155-13164
6. Trost B.M., Thiel O.R., and Tsui H.-C. J. Am. Chem. Soc. 124 (2002) 11616-11617
7. Park J.B., Ko S.H., Hong W.P., and Lee K.-J. Bull. Korean Chem. Soc. 25 (2004) 927-930
8. For the synthesis of quinolines, pyridines, and related compounds from Baylis-Hillman adducts in our group, see:. Park D.Y., Lee M.J., Kim T.H., and Kim J.N. Tetrahedron Lett. 46 (2005) 8799-8803
9. Lee M.J., Kim S.C., and Kim J.N. Bull. Korean Chem. Soc. 27 (2006) 439-442
10. Lee C.G., Lee K.Y., Lee S., and Kim J.N. Tetrahedron 61 (2005) 1493-1499
11. Kim S.C., Gowrisankar S., and Kim J.N. Bull. Korean Chem. Soc. 26 (2005) 1001-1004
12. Lee C.G., Lee K.Y., Gowrisankar S., and Kim J.N. Tetrahedron Lett. 45 (2004) 7409-7413
13. Lee K.Y., Kim J.M., and Kim J.N. Tetrahedron 59 (2003) 385-390
14. Kim J.N., Kim H.S., Gong J.H., and Chung Y.M. Tetrahedron Lett. 42 (2001) 8341-8344
15. Kim J.N., Lee H.J., Lee K.Y., and Kim H.S. Tetrahedron Lett. 42 (2001) 3737-3740
16. Kim J.N., Lee K.Y., Kim H.S., and Kim T.Y. Org. Lett. 2 (2000) 343-345
17. For the synthesis of quinolines and related compounds from Baylis-Hillman adducts by other groups, see:. Pathak R., Madapa S., and Batra S. Tetrahedron 63 (2007) 451-460
18. Madapa S., Singh V., and Batra S. Tetrahedron 62 (2006) 8740-8747
19. Narender P., Srinivas U., Ravinder M., Ananda Rao B., Ramesh C., Harakishore K., Gangadasu B., Murthy U.S.N., and Jayathirtha Rao V. Bioorg. Med. Chem. 14 (2006) 4600-4609
20. Basavaiah D., Reddy R.J., and Rao J.S. Tetrahedron Lett. 47 (2006) 73-77
21. Basavaiah D., Reddy R.M., Kumaragurubaran N., and Sharada D.S. Tetrahedron 58 (2002) 3693-3697
22. O'Dell D.K., and Nicholas K.M. J. Org. Chem. 68 (2003) 6427-6430
23. O'Dell D.K., and Nicholas K.M. Tetrahedron 59 (2003) 747-754
24. Familoni O.B., Klaas P.J., Lobb K.A., Pakade V.E., and Kaye P.T. Org. Biomol. Chem. 4 (2006) 3960-3965
25. Familoni O.B., Kaye P.T., and Klaas P.J. Chem. Commun. (1998) 2563-2564
26. Yi H.-W., Park H.W., Song Y.S., and Lee K.-J. Synthesis (2006) 1953-1960
27. Hong W.P., and Lee K.J. Synthesis (2006) 963-968
28. For the synthesis of authentic samples of synthesized quinolines and pyridines, see:. Odle R., Blevins B., Ratcliff M., and Hegedus L.S. J. Org. Chem. 45 (1980) 2709-2710
29. Rosa A.M., Lobo A.M., Branco P.S., Prabhakar S., and Pereira A.M.D.L. Tetrahedron 53 (1997) 269-284
30. Shao H.W., and Cai J.C. Chinese Chem. Lett. 8 (1997) 493-496
31. Leleu S., Papamicael C., Marsais F., Dupas G., and Levacher V. Tetrahedron: Asymmetry 15 (2004) 3919-3928
32. Penhoat M., Levacher V., and Dupas G. J. Org. Chem. 68 (2003) 9517-9520
33. Kanomata N., and Nakata T. Heterocycles 48 (1998) 2551-2558
34. For the palladium-catalyzed aerobic oxidation of amines, see:. Wang J.-R., Fu Y., Zhang B.-B., Cui X., Liu L., and Guo Q.-X. Tetrahedron Lett. 47 (2006) 8293-8297
35. Wang J.-R., Yang C.-T., Liu L., and Guo Q.-X. Tetrahedron Lett. 48 (2007) 5449-5453
36. 3CN, DMF).
37. 4S: C, 65.78; H, 5.52; N, 3.65. Found: C, 65.63; H, 5.85; N, 3.49.
38. For the palladium-mediated synthesis of tetrahydropyridines and tetrahydroquinolines and their synthetic applications, see:. Beccalli E.M., Broggini G., Martinelli M., Masciocchi N., and Sottocornola S. Org. Lett. 8 (2006) 4521-4524
39. Soderberg B.C.G., Hubbard J.W., Rector S.R., and O'Neil S.N. Tetrahedron 61 (2005) 3637-3649
40. Grigg R., and Kordes M. Eur. J. Org. Chem. (2001) 707-712
41. Gai X., Grigg R., Koppen I., Marchbank J., and Sridharan V. Tetrahedron Lett. 44 (2003) 7445-7448
42. Grigg R., Sridharan V., and Thayaparan A. Tetrahedron Lett. 44 (2003) 9017-9019
43. Oh C.H., and Park S.J. Tetrahedron Lett. 44 (2003) 3785-3787