O-alkylation chemistry of neocupferron

Tetrahedron Letters

Volumn 41, Issue 4, 2000, Pages 451-456

  Hou, Yongchun ^a   Xie, Wenhua ^a   Ramachandran, Niroshan ^b   Mutus, Bulent ^b   Janczuk, Adam J ^a   Wang, Peng George ^a  

^a WAYNE STATE UNIVERSITY   (United States)

^b UNIVERSITY OF WINDSOR   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

NAPHTHALENE DERIVATIVE; NITRIC OXIDE;

ALKYLATION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; ISOMERISM; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; X RAY ANALYSIS;

EID: 0034700866     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02091-2     Document Type: Article

References (12)

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2. Beckman, J. S. In The Physiological and Pathological Chemistry of Nitric Oxide, Nitric Oxide, Principles and Actions; Lancaster Jr., J., Ed.; Academic Press: San Diego, 1996, pp. 1-69.
3. Fukuto, J. M. In Chemistry of Nitric Oxide: Biologically Relevant Aspects, Nitric Oxide, Biochemistry, Molecular Biology, and Therapeutic Implications; Ignarro, L.; Murad, F., Eds.; Academic Press, 1995, p. 1.
4. (a). Hou, Y.-C.; Janczuk, A. J.; Wang, P. G. Curr. Pharm. Design 1999, 5(6), 417.
5. (b). Keefer, L. K. Chemtech. 1998, 28, 30.
6. McGill, A. D.; Yang, Y.; Wang, J.; Echegoyen, L.; Wang, P. G. In Redox-Sensitive Nitric Oxide Donors: Nitric Oxide Generation Through Electrolysis, Methods in Enzymology; Packer, L., Ed.; Academic Press: New York, 1999; Vol. 301, pp. 235-242.
7. (a). Taylor, D. K.; Bytheway, I.; Barton, D. H. R.; Bayse, C. A.; Hall, M. B. J. Org. Chem. 1995, 60, 443.
8. (b) Balaban, A. T.; Garfield, R. E.; Lesko, M. J.; Seitz, W. A. Org. Prep. Proced. Int. 1998, 30, 439.
9. (c). Garfield, R. E.; Balaban, A. T.; Seitz, W. A.; Klein, D. J.; Lesko, M. US Patent 5,698,738 (Dec. 16, 1997); International Patent Application PCT/US/96/0694 (May 15, 1996).
10. Compound (1,4) naphthoquinone O-methyl-oxime oxime has been reported by Chantot et al., however, it was not synthesized from O-alkylation of neocupferron. See: Chantot, J.-F.; Dargelos, A. C. R. Hebd. Seances Acad. Sci. Ser. C. 1972, 274, 2001.
11. 2)
12. Chertnova, L. F.; Marchenko, G. A.; Kovalenko, V. I.; Struchkov, Yu. T. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1988, 37, 2266.