A simple synthesis of 2-substituted-4H-3,1-benzoxazin-4-ones by palladium-catalyzed cyclocarbonylation of o-iodoanilines with acid chlorides

Organic Letters

Volumn 1, Issue 10, 1999, Pages 1619-1622

  Larksarp, Chitchamai ^a   Alper, Howard ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001166398     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990258y     Document Type: Article

References (32)

1. (a) Hedstrom, L.; Moorman, A. R.; Dobbs, J.; Abeles, R. H. Biochemistry 1984, 23, 1753.
2. (b) Krantz, A.; Spencer, R. W.; Tam, T. F.; Liak, T. J.; Copp, L. J.; Thomas, E. M.; Rafferty, S. P. J. Med. Chem. 1990, 33, 464.
3. (c) Stein, R. L., Strimpler, A. M., Viscarello, B. R., Wildonger, R. A., Mauger, R. C. Trainor, D. A. Biochemistry 1987, 26, 4126.
4. (d) Hays, S. J.; Caprathe, B. W.; Gilmore, J. L.; Amin, N.; Emmerling, M. R.; Michael, W.; Nadimpali, R.; Nath, R.; Raser, K. J.; Stafford, D.; Watson, D.; Wang, K.; Jaen, J. C. J. Med. Chem. 1998, 41, 1060.
5. (e) Fenton, G., Newto, C. G., Wyman, B. M., Bagge, P., Dron, D. I. Riddell, D. Jones, G. D. J. Med. Chem. 1989, 32, 265.
6. (a) Habib, O. M.; Moawad, E. B.; Girges, M. M.; El-Shafei, A. M. Boll. Chim. Farm. 1995, 134, 503.
7. (b) Errede, L. A.; Oien, H. T.; Yarian, D. R. J. Org. Chem. 1977, 42, 12.
8. (c) Ibrahim, S. S.; Abdel-Halim, A. M.; Gabr, Y.; El-Edfawy, S.; Abdel-Rahman, R. J. Chem. Res., Synop. 1997, 154.
9. (d) Shaban, M. A. E.; Taha, M. A. M.; Sharshira, E. M. Advances in Heterocyclic Chemistry; Academic Press: San Diego, 1991; Vol. 52.
10. Clémence, F.; Le Martret, O.; Collard, J. J. Heterocycl. Chem. 1984, 21, 1345.
11. For a recent review in the chemistry of 4H-3,1-benzoxazin-4-ones, see: Coppola, G. M. J. Heterocycl. Chem. 1999, 36, 563 and references therein.
12. (a) Bain, D. I.; Smalley, R. K. J. Chem. Soc. C 1968, 1593.
13. (b) Johnson, J. L.; Pattison, I. J. Heterocycl. Chem. 1986, 23, 249.
14. (c) Beck, J. R.; Yahner, J. A. J. Org. Chem. 1973, 38, 2450.
15. (a) Zentmyer, D. T.; Wagner, E. C. J. Org. Chem. 1949, 14, 967.
16. (b) Balsubramaniyan, V.; Argade, N. P. Tetrahedron Lett. 1986, 27, 2487.
17. (c) Papadopoulos, E. P.; Torres, C. D. Heterocycles 1982, 19, 1039.
18. (d) Papadopoulos, E. P.; Torres, C. D. J. Heterocycl. Chem. 1982, 19, 269.
19. Minami, T.; Ogata, M.; Hirao, I. Synthesis 1982, 231.
20. (a) Bristow, T. H. C., Foster, H. E., Hooper, M. J. Chem. Soc., Chem. Commun. 1974, 677.
21. (b) Richman, R. J., Hassner, A. J. Org. Chem. 1968, 33, 2548.
22. (c) Adam. J., Winkler, T. Helv. Chim. Acta 1984, 67, 2186.
23. (a) Crabtree, H. E., Smalley, R. K., Suschitzky, H. J. Chem. Soc. C 1968, 2730.
24. (b) Smalley, R. K., Suschitzky, H. Tetrahedron Lett. 1966, 29, 3465.
25. (c) Archer, J. G., Barker, A. J., Smalley, R. K. J. Chem. Soc., Perkin Trans, 1 1973, 1169.
26. Molina, P.; Conesa, C.; Velasco, M. D. Tetrahedron Lett. 1993, 34, 175.
27. Gordeev, M. F. Biotechnol. Bioeng. 1998, 61, 13.
28. Larock, R. C., Fellows, C. A. J. Org. Chem. 1980, 45, 363.
29. Cacchi, S., Fabrizi, G., Marinelli, F. Synlett 1996, 997.
30. 2NEt (3.0 mmol), and dry THF (5.0 mL) was reacted in an autoclave at 300 psi of carbon monoxide for 24 h at 100°C. The reaction mixture was cooled to room temperature, and excess carbon monoxide was released. The reaction mixture was filtered, and the filtrate was concentrated by rotary evaporation. The residue was purified by silica gel column chromatography using 1:1 ether:n-pentane as the eluant.
31. (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987; p 725.
32. (b) McCrindle, R.; Ferguson, G.; Arsenault, G. J.; McAlees, A. J.; Stephenson, D. K. J. Chem. Res., Synop. 1984, 360.