Synthesis and aqueous chemistry of α-acetoxy-N-nitrosomorpholine: Reactive intermediates and products

Journal of Organic Chemistry

Volumn 71, Issue 1, 2006, Pages 202-209

  Zink, Charles N ^a   Kim, Hyun Joong ^a   Fishbein, James C ^a  

^a UNIVERSITY OF MARYLAND BALTIMORE COUNTY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; CATALYSIS; HYDROLYSIS; OXIDATION; PH EFFECTS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

AQUEOUS CHEMISTRY; ELECTRONIC EFFECTS; METABOLIC ACTIVATION; NITROSO NITROGEN;

NITROGEN COMPOUNDS;

2 (1H BENZO[D]IMIDAZOL 1 YL)ETHANOL; 2 [2 (1H BENZO[D]IMIDAZOL 1 YL)ETHOXY]ACETALDEHYDE; ACETALDEHYDE; ALPHA ACETOXY N NITROSOMORPHOLINE; ALPHA ACETOXY N NITROSOPIPERIDINE; CYANIDE; DINITROPHENYLHYDRAZONE; DNA; HYDRAZONE DERIVATIVE; IMINE; METHANOL; MORPHOLINE DERIVATIVE; N ACETYLMORPHOLINE; N NITROSOMORPHOLINIC ACID; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; DECOMPOSITION; HYDRATION; IONIC STRENGTH; OXIDATION; PH; REACTION ANALYSIS; SYNTHESIS; TEMPERATURE DEPENDENCE;

ACETALDEHYDE; BUFFERS; ETHANOL; IMIDAZOLES; KINETICS; MOLECULAR STRUCTURE; N-NITROSOPYRROLIDINE; NITROSAMINES; SOLUTIONS;

EID: 31344445205     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051936z     Document Type: Article

References (53)

1. Loeppky, R. N.; Michejda, C. J. Nitrosamines and Related N-Nitroso Compounds; American Chemical Society: Washington, DC, 1994; Vol. 553.
2. Lijinsky, W. Chemistry and Biology of N-Nitroso Compounds; Cambridge University Press: Cambridge, U.K., 1992.
3. Preussmann, R.; Eisenbrand, G. In Chemical Carcinogens, Vol. 2; Searle, C. S., Ed.; American Chemical Society: Washington, DC, 1984; Vol. 182, pp 829-868.
4. Charrois, J. W.; Arend, M. W.; Froese, K. L.; Hrudey, S. E. Environ. Sci. Technol. 2004, 38, 4835-4841.
5. Spiegelhalder, B.; Preussmann, R. J. Cancer Res. Clin. Oncol. 1984, 108, 160-163.
6. Dallinga, J. W.; Pachen, D. M.; Lousberg, A. H.; van Geel, J. A.; Houben, G. M.; Stockbrugger, R. W.; van Maanen, J. M.; Kleinjans, J. C. Cancer Lett. 1998, 124, 119-125.
7. van Maanen, J. M.; Pachen, D. M.; Dallinga, J. W.; Kleinjans, J. C. Cancer Detect. Prev. 1998, 22, 204-212.
8. Reh, B. D.; Fajen, J. M. Am. Ind. Hyg. Assoc. J. 1996, 57, 918-923.
9. Fajen, J. M.; Carson, G. A.; Rounbehler, D. P.; Fan, T. Y.; Vita, R. Science 1979, 205, 1262-1264.
10. Oury, B.; Limasset, J. C.; Protois, J. C. Int. Arch. Occup. Environ. Health 1997, 70, 261-271.
11. Straif, K.; Weiland, S. K.; Bungers, M.; Holthenrich, D.; Taeger, D.; Yi, S.; Keil, U. Occup. Environ. Med. 2000, 57, 180-187.
12. Hecht, S. S.; Young, R. Cancer Res. 1981, 41, 5039-5043.
13. Loeppky, R. N.; Ye, Q.; Goelzer, P.; Chen, Y. Chem. Res. Toxicol. 2002, 15, 470-482.
14. Park, M.; Loeppky, R. N. Chem. Res. Toxicol. 2000, 13, 72-81.
15. Loeppky, R. N.; Cui, W.; Goelzer, P.; Park, M.; Ye, Q. IARC Sci. Publ. 1999, 150, 155-168.
16. Loeppky, R. N. Drug. Metab. Rev. 1999, 31, 175-193.
17. Loeppky, R. N.; Fuchs, A.; Janzowski, C.; Humberd, C.; Goelzer, P.; Schneider, H.; Eisenbrand, G. Chem. Res. Toxicol. 1998, 11, 1556-1566.
18. Loeppky, R. N.; Goelzer, P. Chem. Res. Toxicol. 2002, 15, 457-469.
19. Park, M.; Gu, F.; Loeppky, R. N. Tetrahedron Lett. 1998, 39, 1287-1290.
20. Loeppky, R. N.; Xiong, H. J. Labeled Compd. Radiopharm. 1994, 34, 1099-1110.
21. Jarman, M.; Manson, D. Carcinogenesis 1986, 7, 559-565.
22. Kim, H. J.; Fishbein, J. C. Chem. Res. Toxicol. 2003, 16, 715-720.
23. Searle, C. E. Chemical Carcinogens, 2nd ed.; American Chemical Society: Washington, DC, 1984; Vol. 1.
24. Vigroux, A.; Kresge, A. J.; Fishbein, J. C. J. Am. Chem. Soc. 1994, 117, 4433-4434.
25. Rajamaki, M.; Vigroux, A.; Chahoua, L.; Fishbein, J. C. J. Org. Chem. 1995, 60, 2324-2325.
26. Revis, C. L.; Rajamaki, M.; Fishbein, J. C. J. Org. Chem. 1995, 60, 7733-7738.
27. Cai, H.; Fishbein, J. C. Tetrahedron 1997, 53, 10671-10676.
28. Cai, H.; Fishbein, J. C. J. Am. Chem. Soc. 1999, 121, 1826-1833.
29. Chahoua, L.; Vigroux, A.; Chiang, Y.; Fishbein, J. C. Can. J. Chem. 1999, 77, 1148-1161.
30. Chahoua, L.; Cai, H.; Fishbein, J. C. J. Am. Chem. Soc. 1999, 121, 5161-5169.
31. Chahoua, L.; Mesic, M.; Revis, C. L.; Vigroux, A.; Fishbein, J. C. J. Org. Chem. 1997, 62, 2500-2504.
32. Hecht, S. S.; Chen, C. B. J. Org. Chem. 1979, 44, 1563-1566.
33. Young-Sciame, R.; Wang, M.; Chung, F.; Hecht, S. S. Chem. Res. Toxicol. 1995, 8, 607.
34. Wang, M.; Young-Sciame, R.; Chung, F.; Hecht, S. S. Chem. Res. Toxicol. 1995, 8, 617.
35. Chung, F.-L.; Wang, M.; Hecht, S. S. Canc. Res. 1989, 49, 2034.
36. Wang, M.; Chung, F. L.; Hecht, S. S. Chem. Res. Toxicol. 1989, 2, 423-428.
37. Stewart, B. W.; Swann, P. F.; Holsman, J. W.; Magee, P. N. Z. Krebsforsch. Klin. Onkol. Cancer Res. Clin. Oncol. 1974, 82, 1-12.
38. Loeppky, R. N.; Ye, Q.; Goelzer, P.; Chen, Y. Chem. Res. Toxicol. 2002, 15, 470-482.
39. Asher, V.; Becu, C.; Anteunis, M. J. O.; Callens, R. Tetrahedron Lett. 1981, 22, 141-144.
40. Saavedra, J. E. J. Org. Chem. 1979, 44, 4511-4517.
41. Chahoua, L.; Mesic, M.; Revis, C.; Fishbein, J. C. J. Org. Chem. 1997, 62, 2500-2504.
42. Mochizuki, M.; Anjo, T.; Takeda, K.; Suzuki, E.; Sekiguchi, N.; Huang, G. F.; Okada, M. IARC Sci. Publ. 1980, 41, 553-559.
43. Mochizuki, M.; Anjo, T.; Sekiguchi, N.; Ikarashi, A.; Suzuki, A.; Wakabayashi, Y.; Okada, M. Chem. Pharm. Bull. 1986, 34, 4.
44. Mochizuki, M.; Anjo, T.; Wakabayashi, Y.; Sone, T.; Okada, M. Tetrahedron Lett. 1980, 21, 1761-1764.
45. Mochizuki, M.; Anjo, T.; Okada, M. Chem. Pharm. Bull. 1978, 26, 6.
46. Okada, M.; Mochizuki, M.; Anjo, T.; Sone, T.; Wakabayashi, Y.; Suzuki, E. IARC Sci. Publ. 1980, 31, 71-82.
47. Lu, X.; Heilman, J. M.; Blans, P.; Fishbein, J. C. Chem. Res. Toxicol. 2005, 1462-1470.
48. Sollenberger, P. Y.; Martin, R. B. J. Am. Chem. Soc. 1970, 92, 4261-4270.
49. Karabatsos, G. J.; Taller, R. A. J. Org. Chem. 1964, 29, 4373.
50. Barton, J. E.; Clinch, K.; O'Hanlon, P.; Ormrod, J.; Rice, M.; Turnbull, M. International Patent Application WO 9319599, 1993.
51. Hill, S. T.; Mokotoff, M. J. Org. Chem. 1984, 49, 1441-1442.
52. Chen, Y. (Pfizer Inc.). European Patent Application Ep88-300425.1, 1988.
53. Stecher, P. G., Ed. The Merck Index, 8th ed.; Merck & Co.: Rahway, NJ, 1968.