On the cyclization of acyliminium salts derived from pyroglutamic acid

Tetrahedron Letters

Volumn 37, Issue 4, 1996, Pages 485-486

  Rigo, Benoît ^a   El Ghammarti, Samira ^a   Couturier, Daniel ^b  

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

^b UNIV LILLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PYROGLUTAMIC ACID DERIVATIVE; QUATERNARY AMMONIUM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030070032     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02215-5     Document Type: Article

References (13)

1. Many 5-aryl-2-pyrrolidinones possess a psychotropic activity: UCB, SA, Ger. Patent 1972, 2, 136,57; Chem. Abstr. 1972, 76, 113055 y; Lednicer, D.; Mitscher, L.A. The Organic Chemistry of Drug Synthesis; Wiley and Sons, Inc., New York,. 1977; vol. 1 pp. 235; Bocchi, V.; Gardini, G.P.; Pinza, M. Farmaco, Ed. Sci. 1971, 26, 429-434.
2. Many 5-aryl-2-pyrrolidinones possess a psychotropic activity: UCB, SA, Ger. Patent 1972, 2, 136,57; Chem. Abstr. 1972, 76, 113055 y; Lednicer, D.; Mitscher, L.A. The Organic Chemistry of Drug Synthesis; Wiley and Sons, Inc., New York,. 1977; vol. 1 pp. 235; Bocchi, V.; Gardini, G.P.; Pinza, M. Farmaco, Ed. Sci. 1971, 26, 429-434.
3. Many 5-aryl-2-pyrrolidinones possess a psychotropic activity: UCB, SA, Ger. Patent 1972, 2, 136,57; Chem. Abstr. 1972, 76, 113055 y; Lednicer, D.; Mitscher, L.A. The Organic Chemistry of Drug Synthesis; Wiley and Sons, Inc., New York,. 1977; vol. 1 pp. 235; Bocchi, V.; Gardini, G.P.; Pinza, M. Farmaco, Ed. Sci. 1971, 26, 429-434.
4. a) Rigo, B.; Fasseur, D.; Cherepy, N.; Couturier, D. Tetrahedron Lett. 1989, 30, 7057-7060;
5. b) Maryanoff, D.F.; McComsey, B.E.; Duhl-Emswiler, B.A. J. Org. Chem. 1983, 48, 5062-5074.
6. Iwasaki, T.; Horikawa, H.; Matsumoto, K.; Miyoshi, M. J. Org. Chem. 1979, 44, 1552-1554.
7. Acids 3 were obtained from the reaction of N,O-bis trimethylsilyl pyroglutamic acid with N-chloromethyl acetanilides: El Ghammarti S. Etude des voies de synthèse de bioisostères de la néothramycine, Thesis, USTL Lille France, 1995; these syntheses will be described in another publication.
8. For related reactions see : Hubert, J.C.; Wijnberg, J.B.P.A.; Speckamp, W.N. Tetrahedron 1975, 31, 1437-1441; Wijnberg, J.B.P.A.;. Speckamp, W.N.; de Boer, J.J.J. Tetrahedron Lett. 1974, 46, 4077-4080.
9. For related reactions see : Hubert, J.C.; Wijnberg, J.B.P.A.; Speckamp, W.N. Tetrahedron 1975, 31, 1437-1441; Wijnberg, J.B.P.A.;. Speckamp, W.N.; de Boer, J.J.J. Tetrahedron Lett. 1974, 46, 4077-4080.
10. Rigo, B.; Kolocouris, N. J. Heterocyclic Chem. 1983, 20, 893-898; Rigo, B.; Gautret, P.; Legrand, A.; El Ghammarti, S.; Couturier, D. Synth. Commun. 1994, 24, 2609-2615.
11. Rigo, B.; Kolocouris, N. J. Heterocyclic Chem. 1983, 20, 893-898; Rigo, B.; Gautret, P.; Legrand, A.; El Ghammarti, S.; Couturier, D. Synth. Commun. 1994, 24, 2609-2615.
12. Yasuda, S.; Yamamoto, Y.; Yoshida S.; Hanaoka, M. Chem. Pharm. Bull. 1988, 36, 4229-4236.
13. 2) δ 1.7-1.90 (m, 1H), 2.3-2.7 (m, 3H), 3.76(s, 3H), 3.78 (s, 3H), 3.8 (bs, deuterium oxide exchangeable, 1H), 4.09 (d, J = 10.9 Hz, 1H), 4.9-5 (m, 1H), 5.23 (d, J = 10.9 Hz, 1H), 6.24 (d, J = 8.7 Hz, 1H=, 6.62 (d, J = 8.7 Hz, 1H).