Efficient synthesis of tricyclic benzobisoxazines by silica gel catalysis

Journal of Organic Chemistry

Volumn 72, Issue 5, 2007, Pages 1867-1869

  Spagnol, Gaëlle ^a   Rajca, Andrzej ^a   Rajca, Suchada ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CONDENSATION REACTIONS; DERIVATIVES; KETONES; SILICA GEL; SYNTHESIS (CHEMICAL);

NONSYMMETRIC DERIVATIVES; OXAZINE RING; SILICA GEL CATALYSIS; TRICYCLIC BENZOBISOXAZINES;

AMINES;

BENZENE DERIVATIVE; OXAZINE DERIVATIVE; SILICA GEL;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; POLYMERIZATION; SYNTHESIS;

ALDEHYDES; BENZOXAZINES; CATALYSIS; CHROMATOGRAPHY, THIN LAYER; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; SILICON DIOXIDE;

EID: 33847622915     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062670e     Document Type: Article

References (27)

1. (a) Wang, C. F.; Su, Y. C.; Kuo, S. W.; Huang, C. F.; Sheen, Y. C.; Chang, F. C. Angew. Chem., Int. Ed. 2006, 45, 2248.
2. (b) Lin, C. H.; Cai, S. X.; Leu, T. S.; Hwang, T. Y.; Lee, H. H. J. Polym. Sci. A 2006, 44, 3454.
3. (c) Ishida, H.; Ohba, S. Polymer 2005, 46, 5588.
4. (d) Burke, W. J. J. Am. Chem. Soc. 1949, 71, 609.
5. Biologically active 1,3-benzoxazine derivatives. (a) Scarborough, R. M.; Venkatraman, M. S.; Zhang, X.; Pandey, A. U.S. Pat. Appl. Publ. 2006.
6. (b) Urbanski, T.; Radzikowski, Cz.; Ledochowski, Z.; Czarnocki, W. Nature 1956, 178, 1351.
7. (c) Urbanski, T.; Slopek, S. Nature 1951, 168, 562.
8. (a) Recent review on biologically active 1,4-benzoxazine derivatives: Achari, B.; Mandal, S. B.; Dutta, P. K.; Chowdhury, C. Synlett 2004, 2449.
9. (b) Asymmetric synthesis and biological activity of levofloxacin, a potent 1,4-benzoxazine-based antibacterial: Mitscher, L. A.; Sharma, P. N.; Chu, D. T. W.; Shen, L. L.; Pernet, A. G. J. Med. Chem. 1987, 30, 2283.
10. Gromachevskaya, E. V.; Kvitkowskii, F. V.; Kosulina, T. P.; Kulnevich, V. G. Chem. Heterocycl. Compd. Chem. 2003, 39, 137.
11. Zhang, P.; Terefenko, E. A.; Fensome, A.; Zhang, Z.; Zhu, Y.; Cohen, J.; Winneker, R.; Wrobel, J.; Yardley, J. Bioorg. Med. Chem. Lett. 2002, 12, 787.
12. (a) Fensome, A.; Bender, R.; Chopra, R.; Cohen, J.; Collins, M. A.; Hudak, V.; Malakian, K.; Lockhead, S.; Olland, A.; Svenson, K.; Terefenko, E. A.; Unwalla, R. J.; Wilhelm, J. M.; Wolfrom, S.; Zhu, Y.; Zhang, Z.; Zhang, P.; Winneker, R. C.; Wrobel, J. J. Med. Chem. 2005, 48, 5092.
13. (b) Zhang, Z.; Olland, A. M.; Zhu, Y.; Cohen, J.; Berrodin, T.; Chippari, S.; Appavu, C.; Li, S.; Wilhem, J.; Chopra, R.; Fensome, A.; Zhang, P.; Wrobel, J.; Unwalla, R. J.; Lyttle, C. R.; Winneker, R. C. J. Biol. Chem. 2005, 280, 28468.
14. Charmantray, F.; Demeunynck, M.; Carrez, D.; Croisy, A.; Lansiaux, A.; Bailly, C.; Colson, P. J. Med. Chem. 2003, 46, 967.
15. N-Haloacetyl 1,2-dihydro-4H-3,1-benzoxazines with herbicidal activity: Kobzina, J. W. Chem. Abstr. 1977, 87, 79678e. Kobzina, J. W. U.S. Patent 3,917,592, 1975.
16. Holly, F. W.; Cope, A. C. J. Am. Chem. Soc. 1944, 66, 1875.
17. Annelation of (2-iodophenyl)acetonitrile onto sterically hindered propargylic alcohols was reported to produce 1,2-dihydro-4H-3,1-benzoxazine derivatives in moderate yields: Tian, Q.; Pletnev, A. A.; Larock, R. C. J. Org. Chem. 2003, 68, 339.
18. Rassat, A.; Sieveking, U. Angew. Chem., Int. Ed. 1972, 11, 303.
19. (a) Nguyen, T. T.; Amey, R. L.; Martin, J. C. J. Org. Chem. 1982, 47, 1024.
20. (b) Neuvonen, K.; Pohtola, R.; Pihlaja, K. Magn. Reson. Chem. 1989, 27, 725.
21. (c) Oka, H.; Tamura, T.; Miura, Y.; Teki, Y. J. Mater. Chem. 2001, 11, 1364.
22. Two 3,1-oxazine rings could be annelated to acridine using relatively reactive formaldehyde ref 7.
23. (a) Rajca, A.; Wongsriratanakul, J.; Rajca, S. Science 2001, 294, 1503.
24. (b) Rajca, A. Adv. Phys. Org. Chem. 2005, 40, 153.
25. Rajca, A.; Takahashi, M.; Pink, M.; Spagnol, G.; Rajca, S. To be submitted.
26. Banerjee, A. K.; Mimo, M. S. L.; Vegas, W. J. V. Russ. Chem. Rev. 2001, 70, 971.
27. Spagnol, G.; Shiraishi, K.; Rajca, S.; Rajca, A. Chem. Commun. 2005, 5047.