Mechanism of racemization of 3-hydroxy-1,4-benzodiazepines in alcoholic solvents

Enantiomer

Volumn 3, Issue 6, 1998, Pages 485-490

  Yang, Shen K ^a  

^a Uniformed Services University of the Health Sciences and the Walter Reed National Military Medical Center   (United States)

Author keywords

Chiral stationary phase; Circular dichroism spectropolarimetry; HPLC; Lorazepam; Lormetazepam; Oxazepam; Racemization kinetics; Straight chain alcohols; Temazepam

Indexed keywords

ALCOHOL; BUTANOL; HEXANOL; LORAZEPAM; LORMETAZEPAM; METHANOL; OXAZEPAM; PENTANOL; PROPANOL; SOLVENT; TEMAZEPAM;

ARTICLE; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERISM; POLARIMETRY; PRIORITY JOURNAL; TEMPERATURE;

EID: 0032427594     PISSN: 10242430     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (23)

1. A. Corbella, P. Gariboldi, G. Jommi, A. Forgione, F. Marcucci, P. Martelli, E. Mussini and F. Mauri, J. Chem. Soc. Chem. Commun., 1973, 721.
2. M. Stromar, V. Sunjic, T. Kovac, L. Klasinc and F. Kajfez, Croatica Chemica Acta, 1974, 46, 265.
3. G. Lhoest and A. Frigerio, Advances in Mass Spectrometry in Biochemistry and Medicine, 1976, 2, 339.
4. G. Blaschke and H. Markgraf, Chem. Ber., 1980, 113, 2031.
5. Y. Aso, S. Yoshioka, T. Shibazaki and M. Uchiyama, Chem. Pharm. Bull., 1988, 36, 1834.
6. S.K. Yang and X.L. Lu, J. Pharm. Sci. 1989, 78, 789.
7. X.L. Lu and S.K. Yang, J. Chromatogr., 1990, 535, 229.
8. S.K. Yang and X.L. Lu, Chirality, 1991, 3, 212.
9. S.K. Yang and X.L. Lu, Chirality, 1992, 4, 443.
10. S.C. Bell and S.J. Childress, J. Org. Chem., 1964, 29, 506.
11. A. Forgione, P. Martelli, F. Marcucci, R. Fanelli, E. Mussini and G.C. Jommi, J. Chromatogr., 1971, 59, 163.
12. W. Sadée and E. Van der Kleijn, J. Pharm. Sci., 1971, 60, 135.
13. V. Sunjic, M. Oklobdzija, A. Lisini, A. Sega, F. Kajfez, D. Srzic and L. Klasinc, Tetrahedron, 1979, 35, 2531.
14. D. Srzic, L. Klasinc, B. Belin, F. Kajfez and V. Sunjic, Recent Development in Mass Spectrometry and Biochemistry in Medicine, 1979, 2, 149.
15. S.K. Yang, Chirality, 1995, 7, 365.
16. S.K. Yang, J. Pharm. Sci., 1994, 83, 898.
17. S.K. Yang, Z. Bao and M. Shou, Chirality, 1996, 8, 214.
18. S.K. Yang, Z. Bao and M. Shou, J. Labelled Compd. Radiopharm., 1995, 36, 861.
19. S.K. Yang, R. Tang and Q.L. Pu, J. Labelled Compds. Radiopharm., 1996, 38, 753.
20. W.H. Pirkle and A. Tsipouras, J. Chromatogr., 1984, 291, 291.
21. M. Jung and V. Schurig, J. Am. Chem. Soc., 1992, 114, 529.
22. E.S. Gould, Mechanism and Structure in Organic Chemistry, Holt, Rinehart and Winston, NY, 1959, p. 181.
23. P. Zuman and R.C. Patel, Techniques in Organic Reaction Kinetics, Krieger Publishing Co., Malabar, FL, 1992, p. 192.