One-step conversion of aldehydes to oxazolines and 5,6-dihydro-4H-1,3-oxazines using 1,2- and 1,3-azido alcohols

Journal of Organic Chemistry

Volumn 61, Issue 7, 1996, Pages 2484-2487

  Badiang, Jennifer G ^a   Aubé, Jeffrey ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 OXAZINE DERIVATIVE; OXAZOLINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029916844     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9521256     Document Type: Article

References (25)

1. (a) Boyer, J. H.; Hamer, J. J. Am. Chem. Soc. 1955, 77, 951-964.
2. (b) Boyer, J. H.; Canter, F. C.; Hamer, J.; Putney, R. K. J. Am. Chem. Soc 1956, 78, 325-327.
3. (c) Boyer, J. H.; Morgan, L. R., Jr. J. Org. Chem. 1959, 24, 561-562.
4. (a) Aubé, J.; Milligan, G L.; Mossman, C. J. J. Org. Chem. 1992, 57, 1635-1637.
5. (b) Aubé, J; Rafferty, P. S.; Milligan, G. L. Heterocycles 1993, 35, 1141-1147.
6. (c) Aubé, J.; Milligan, G. L. J. Am. Chem. Soc. 1991, 113, 8965-8966.
7. (d) Pearson, W. H.; Schkeryantz, J. M. Tetrahedron Lett. 1992, 33, 5291-5294.
8. (e) Pearson, W. H.; Walavalkar, R.; Schkeryantz, J. M.; Fang, W.-K.; Blickensdorf, J. D. J. Am. Chem. Soc. 1993, 115, 10183-10194.
9. (f) Pearson, W. H.; Fang, W.-K.; Kampf, J. W. J. Org. Chem. 1994, 59, 2682-2684.
10. (g) Aubé, J.; Milligan, G. L.; Mossman, C. J. J. Am. Chem Soc. 1995, 117, 10449-10459.
11. Aubé, J.; Gracias, V.; Milligan, G. L. J. Am. Chem Soc. 1995, 117, 8047-8048.
12. For reviews, see: (a) Frump, J. A. Chem. Rev. 1971, 71, 483-505. (b) The Chemistry of Heterocyclic Compounds; Turchi, J., Ed.; John Wiley and Sons, Inc.: New York, 1986; Vol. 45. (c) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297-2360.
13. For reviews, see: (a) Frump, J. A. Chem. Rev. 1971, 71, 483-505. (b) The Chemistry of Heterocyclic Compounds; Turchi, J., Ed.; John Wiley and Sons, Inc.: New York, 1986; Vol. 45. (c) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297-2360.
14. For reviews, see: (a) Frump, J. A. Chem. Rev. 1971, 71, 483-505. (b) The Chemistry of Heterocyclic Compounds; Turchi, J., Ed.; John Wiley and Sons, Inc.: New York, 1986; Vol. 45. (c) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297-2360.
15. Markó, I. E.; Mekhalfia, A. Tetrahedron Lett. 1991, 32, 4779-4782.
16. Carrié, R.; Carboni, B.; Vaultier, M. Tetrahedron 1987, 43, 1799-1180.
17. Levy, A.; Litt, M. J. Polym. Sci., Part B: Polym. Phys. 1967, 5, 881-886.
18. Wenker, H. J. Am. Chem. Soc. 1938, 60, 2152-2155.
19. Pridgen, L. N.; Killmer, L. B.; Webb, R. L. J. Org. Chem. 1982, 47, 1985-1989.
20. Levy, A.; Bassin, T. G.; Litt, M. J. Polym. Sci., Part B. Polym. Phys. 1967, 5, 871-879.
21. Wagner-Jauregg, T.; Roth, M. Chem. Ber. 1960, 93, 3036-3047.
22. Elfeldt, P. Chem. Ber. 1891, 24, 3218-3228.
23. Leffler, M. T.; Adams, R. J. Am. Chem. Soc. 1937, 59, 2252-2258.
24. Kwiatkowski, M.; Sund, C.; Ylikoski, J. Synthesis 1987, 9, 853-854.
25. Rehlander, P. Chem. Ber. 1894, 27, 2154-2161.