A Facile Synthesis of 4-Arylidene-2-substituted Isoxazolidin-5-ones from Baylis-Hillman Acetates

Bulletin of the Korean Chemical Society

Volumn 25, Issue 1, 2004, Pages 33-34

  Lee, Ka Young ^a   Lee, Chang Gon ^a   Kim, Taek Hyeon ^a   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

Author keywords

Baylis Hillman acetates; Isoxazolidin 5 ones; Lithium perchlorate; N Alkylhydroxylamines

Indexed keywords

5 ISOXAZOLIDINONE DERIVATIVE; ACETIC ACID DERIVATIVE; ESTER DERIVATIVE; HETEROCYCLIC COMPOUND; HYDROXYLAMINE; ISOXAZOLIDINE DERIVATIVE; METHOXYAMINE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; BAYLIS HILLMAN REACTION; CHEMICAL REACTION; CYCLIZATION; REACTION ANALYSIS; REPRODUCIBILITY; ROOM TEMPERATURE; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS; TECHNIQUE; TEMPERATURE SENSITIVITY;

EID: 1642544087     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2004.25.1.033     Document Type: Article

References (24)

1. Lee, K. Y.; Kim, J. M.; Kim, J. N. Tetrahedron Lett. 2003, 44, 6737.
2. Baldwin, J. E.; Harwood, L. M.; Lombard, M. J. Tetrahedron 1984, 40, 4363.
3. (a) Baldwin, S. W.; Aube, J. Tetrahedron Lett. 1987, 28, 179.
4. (b) Xiang, Y.; Gi, H.-J.; Niu, D.; Schinazi, R. F.; Zhao, K. J. Org. Chem. 1997, 62, 7430.
5. (c) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. J. Org. Chem. 2000, 65, 5575.
6. (d) Maciejewski, P. I.; Belzecki, C.; Chmielewski, M. Tetrahedron 1992, 48, 10363.
7. (e) Pan, S.; Wang, J.; Zhao, K. J. Org. Chem. 1999, 64, 4.
8. (f) Langlois, N.; Calvez, O.; Radom, M.-O. Tetrahedron Lett. 1997, 38, 8037.
9. (g) Ishikawa, T.; Nagai, K.; Kudoh, T.; Saito, S. Synlett 1998, 1291.
10. (a) Shindo, M.; Itoh, K.; Tsuchiya, C.; Shishido, K. Org. Lett. 2002, 4, 3119.
11. (b) Niu, D.; Zhao, K. J. Am. Chem. Soc. 1999, 121, 2456.
12. (c) Sibi, M. P.; Liu, M. Org. Lett. 2000, 2, 3393.
13. (d) Lee, H.-S.; Park, J.-S.; Kim, B. M.; Gellman, S. H. J. Org. Chem. 2003, 68, 1575.
14. (e) Kang, H. Y.; Cho, Y. S.; Koh, H. Y.; Chang, M. H. Chem. Lett. 1991, 1333.
15. (f) Stamm, H.; Hoenicke, J. Ann. 1971, 748, 143.
16. (a) Moglioni, A. G.; Muray, E.; Castillo, J. A.; Alvarez-Larena, A.; Moltrasio, G. Y.; Branchadell, V.; Ortuno, R. M. J. Org. Chem. 2002, 67, 2402.
17. (b) Ishikawa, T.; Kudoh, T.; Yoshida, J.; Yasuhara, A.; Manabe, S.; Saito, S. Org. Lett. 2002, 4, 1907.
18. The cyclization of 3a is not effective in the presence of p-TsOH or acetic acid in benzene or in toluene.
19. 3) δ 13.90, 22.36, 27.33, 28.51, 31.29, 47.79, 61.91, 123.92, 144.60, 168.41.
20. (a) Kim, J. N.; Kim, J. M.; Lee, K. Y. Synlett 2003, 821.
21. (b) Im, Y. J.; Lee, C. G.; Kim, H. R.; Kim, J. N. Tetrahedron Lett. 2003, 44, 2987.
22. (c) Im, Y. J.; Kim, J. M.; Kim, J. N. Bull. Korean Chem. Soc. 2002, 23, 1361.
23. (d) Im, Y. J.; Na, J. E.; Kim, J. N. Bull. Korean Chem. Soc. 2003, 24, 511.
24. (e) Basanaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811 and further references cited therein.