A convenient method for the conversion of a carboxy group into a 4,6-dimethoxy-1,3,5-triazine group: Application to N-benzylpyroglutamic acids

Synthesis

Volumn , Issue 17, 2006, Pages 2845-2848

  Oudir, Souhila ^a   Rigo, Benoît ^a   Hénichart, Jean Pierre ^b   Gautret, Philippe ^a  

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

^b Faculté des Sciences Pharmaceutiques et Biologiques Université de Lille   (France)

Author keywords

Heterocycles; Imidodicarbonimidate zinc salt; Lactams; Pyroglutamic derivatives; Triazines

Indexed keywords

FUNGI; MOLECULAR SIEVES; REACTION KINETICS; STOICHIOMETRY; ZINC COMPOUNDS;

HETEROCYCLES; IMIDODICARBONIMIDATE ZINC SALT; LACTAMS; PYROGLUTAMIC DERIVATIVES; TRIAZINES;

CARBOXYLIC ACIDS;

1 (2 CHLOROBENZYL) 5 (4,6 DIMETHOXY 1,3,5 TRIAZIN 2 YL)PYRROLIDIN 2 ONE; 1 (4 CHLOROBENZYL) 5 (4,6 DIMETHOXY 1,3,5 TRIAZIN 2 YL)PYRROLIDIN 2 ONE; 1 BENZYL 5 (4,6 DIMETHOXY 1,3,5 TRIAZIN 2 YL)PYRROLIDIN 2 ONE; 2 (DIBROMOMETHYL) 4,6 DIMETHOXY 1,3,5 TRIAZINE; 2 (DICHLOROMETHYL) 4,6 DIMETHOXY 1,3,5 TRIAZINE; 2 (DIETHOXYMETHYL) 4,6 DIMETHOXY 1,3,5 TRIAZINE; 2 (DIMETHOXYMETHYL) 4,6 DIMETHOXY 1,3,5 TRIAZINE; 4,6 DIMETHOXY 1,3,5 TRIAZINE DERIVATIVE; 5 (4,6 DIMETHOXY 1,3,5 TRIAZIN 2 YL) 1 (2 METHYLBENZYL)PYRROLIDIN 2 ONE; 5 (4,6 DIMETHOXY 1,3,5 TRIAZIN 2 YL) 1 (4 METHYLBENZYL)PYRROLIDIN 2 ONE; CARBOXYLIC ACID; ETHYL 4,6 DIMETHOXY 1,3,5 TRIAZINE 2 CARBOXYLATE; METHYL 4,6 DIMETHOXY 1,3,5 TRIAZINE 2 CARBOXYLATE; N BENZYLPYRROLIDINONE DERIVATIVE; PYROGLUTAMIC ACID DERIVATIVE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; POLYMERIZATION; STOICHIOMETRY;

EID: 33748770127     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-942519     Document Type: Article

References (18)

1. (a) Rigo, B.; Lespagnol, C.; Pauly, M. J. Heterocycl. Chem. 1986, 23, 183.
2. (b) Laboratoires Pauly M., EP 135144, 1985; Chem. Abstr. 1985, 103, 123914.
3. Caulier, P.; Couturier, D.; Rigo, B.; Fasseur, D.; Halama, P. J. Heterocycl. Chem. 1993, 30, 921.
4. (a) Fanelli, C.; Fabbri, A. A.; Monti, S.; Menicagli, R.; Pini, D.; Rapaccini, S. M.; Samaritani, S.; Salvadori, P. 7th International Congress of Plant Pathology; Edinburgh: Scotland, 1998.
5. (b) Samaritani, S.; Fabbri, A. A.; Fanelli, C.; Menicagli, R.; Salvadori, P. XXV Convegno Nazionale della Divisione di Chimica Organica; Folgaria: Italy, 1998.
6. (c) Ricelli, A.; Fabbri, A. A.; Fanelli, C.; Menicagli, R.; Samaritani, S.; Pini, D.; Rapaccini, S. M.; Salvadori, P. Restaurator 1999, 97.
7. Rigo, B.; Kolocouris, N. J. Heterocycl. Chem. 1983, 20, 893.
8. (a) Rembarz, G.; Fischer, E.; Roeber, K. Ch.; Ohff, R.; Crahmer, H. J. Prakt. Chem. 1969, 311, 889.
9. (b) Chiang, G. C. US Patent 4933450 A, 1990; Chem. Abstr. 1990, 113, 231414.
10. (c) Gates, P. S.; Jones, G. P.; Saunders, D. E. PCT Int. Appl. WO 9309099 A2, 1993; Chem. Abstr. 1993, 119, 180810.
11. (d) Voss, O.; Dudfield, P. J.; Bauer, K.; Bieringer, H.; Rosinger, C.; Ford, M. J.; Green, D. Ger. Offen. 19521355 A1, 1996; Chem. Abstr. 1997, 126, 144293.
12. (e) Weiss, S.; Krommer, H. US Patent 6342600 B1, 2002; Chem. Abstr. 2002, 136, 134795.
13. Sen, A. B.; Joshi, K. C. J. Indian Chem. Soc. 1948, 25, 483.
14. (a) Grundmann, C.; Kober, E. J. Am. Chem. Soc. 1957, 79, 944.
15. (b) Grundmann, C.; Kober, E. US Patent 3022303, 1962; Chem. Abstr. 1962, 57, 56334.
16. (a) Kober, E. J. Org. Chem. 1961, 26, 2270.
17. (b) Kober, E. H. US Patent 3226386, 1965; Chem. Abstr. 1966, 64, 67883.
18. Kober, E.; Grundmann, C. J. Am. Chem. Soc. 1958, 80, 5547.