Studies on pyrrolidinones. Synthesis of N-benzhydrylpyroglutamic acids and esters

Journal of Heterocyclic Chemistry

Volumn 35, Issue 3, 1998, Pages 567-573

  Rigo, Benoît ^a   Gautret, Philippe ^a   Legrand, Anne ^a   Hénichart, Jean Pierre ^b   Couturier, Daniel ^c  

^a Ecole des Hautes Etudes d'Ingenieur   (France)

^b Universite de Lille   (France)

^c UNIV LILLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; GLUTAMIC ACID DERIVATIVE; PYRROLIDINE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER; CATALYSIS; DRUG SYNTHESIS;

EID: 0031859729     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570350312     Document Type: Article

References (13)

1. The synthesis of compounds 1 will be described in a next publication.
2. B. Rigo, P. Gautret, A. Legrand, J. P. Hénichart and D. Couturier, Synlett, 998 (1997).
3. B. Rigo, C. Lespagnol and M. Pauly, J. Heterocyclic Chem., 25, 49 (1988).
4. B. Rigo and D. Couturier, J. Heterocyclic Chem., 22, 207 (1985).
5. [5a] F. Effenberger, W. Müller and H. Isak, Chem. Ber., 120, 45 (1987);
6. [b] F. Effenberger, W. Müller, R. Keller, W. Wild and T. Ziegler, J. Org. Chem., 55, 3064 (1990).
7. [6a] B. Rigo, C. Lespagnol and M. Pauly, J. Heterocyclic Chem., 25, 59 (1988);
8. [b] B. Rigo, B. Erb, S. El Ghammarti, P. Gautret and D. Couturier, J. Heterocyclic Chem., 32, 1599 (1995).
9. B. Rigo, P. Gautret, A. Legrand, S. El Ghammarti and D. Couturier, Synth. Commun., 24, 2069 (1994).
10. A synthesis of compound 10 by using trimethylsilyl chloride and triethylamine was previously reported [6a]. A more convenient synthesis of 10 from the saccharin catalyzed reaction of pyroglutamic acid with hexamethyldisilazane is described in reference 9.
11. S. El Ghammarti, B. Rigo, H. Meijdi, J.-P. Hénichart and D. Couturier, J. Heterocyclic Chem., to be published.
12. P. Gautret, S. El Ghammarti, A. Legrand, D. Couturier and B. Rigo, Synth. Commun., 26, 707 (1996).
13. A general specific synthesis of each diastereoisomer will be reported in a later publication.