Product analyses of ozone mediated nitration of benzimidazole derivatives with nitrogen dioxide: Formation of 1-nitrobenzimidazoles and conversion to benzotriazoles

Chemical and Pharmaceutical Bulletin

Volumn 52, Issue 5, 2004, Pages 570-576

  Kaiya, Toyo ^a   Nakamura, Kei ^a   Tanaka, Masaru ^a   Miyata, Naoki ^a   Kohda, Kohfuku ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

Benzimidazole; Benzotriazole; Conversion; N nitration; Nitration; Nitrogen dioxide

Indexed keywords

BENZENE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; BENZOTRIAZOLE DERIVATIVE; IMIDAZOLE DERIVATIVE; NITROGEN DIOXIDE; OZONE; PURINE DERIVATIVE; BENZIMIDAZOLE; BENZOTRIAZOLE; NITRATE; TRIAZOLE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; ELECTRON; EXTRACTION; NITRATION; CHEMISTRY;

BENZIMIDAZOLES; NITRATES; NITROGEN DIOXIDE; OZONE; TRIAZOLES;

EID: 16544387268     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.52.570     Document Type: Article

References (21)

1. The author passed away on June 9, 2002 at the age of 63 due to illness. This report is her posthumous work.
2. Hemminki K., Koskinen M., Rajaniemi H., Zhao C., Regul. Toxicol. Pharmacol., 32, 264-275 (2000).
3. Yermilov V., Rubio J., Ohsima H., FEBS Lett., 376, 207-210 (1965).
4. Huang G.-F. (Kohda K.), Torrence P. F., J. Org. Chem., 42, 3821-3824 (1977).
5. Ariza X., Bou V., Vilarrasa J., J. Am. Chem. Soc., 117, 3665-3673 (1995).
6. Ariza X., Farras J., Serra C., Vilarrasa J., J. Org. Chem., 62, 1547-1549 (1997).
7. Suzuki H., Nonoyama N., J. Chem. Res. (S), 1996, 244-245 (1996).
8. Giziewicz J., Wnuk S. F., Robins M. J., J. Org. Chem., 64, 2149-2151 (1999).
9. Deghati P. Y., Wanner M. J., Koomen G.-J., Tetrahedron Lett., 41, 1291-1295 (2000).
10. Sodum R. S., Fiala E. S., Chem. Res. Toxicol., 14, 438-450 (2000).
11. Kaiya T., Tanaka H., Kohda K., Nucleosides Nucleotides Nucleic Acids, 21, 427-433 (2002).
12. Kaiya T., Fujiwara T., Kohda K., Chem. Res. Toxicol., 13, 993-1001 (2000).
13. Kaiya T., Aoyama S., Kohda K., Bioorg. Med. Chem. Lett., 8, 625-630 (1998).
14. Kaiya T., Ohta M., Kohda K., Tetrahedron, 49, 8795-8804 (1993).
15. Mori T., Suzuki H., Synlett, 1995, 383-392 (1995).
16. Kaiya T., Aoyama S., Kohda K., Bioorg. Med. Chem. Lett., 9, 961-964 (1999).
17. Ficken G. E., Fry D. J., J. Org. Chem., 28, 736-738 (1963).
18. Kulibabina T. N., Kuzilina E. V., Malinina L. A., Pevzner M. S., Khim. Geterotsikl. Soedin., 11, 1570-1572 (1976). (CAN 86: 89711, AN 1977: 89711).
19. Habraken C. L., Cohen-Fernandes P., J. Org. Chem., 36, 3084-3086 (1971).
20. Coburn M. D., J. Heterocyclic Chem., 10, 743-746 (1973).
21. Il'ina V. A., Maslennikova T. A., Gal'pern G. M., Filatova N. N., Zhurnal Analiticheskoi Khimii, 36, 1820-1823 (1981). (CAN 96: 14803, AN 1982: 14803).