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

Abstract

Reaction of an activated form of carboxylic acids with a stoichiometric amount of zinc dimethyl imidodicarbonimidate (in CH₂Cl₂-pyridine with molecular sieves), led to 4,6-dimethoxy-1,3,5-triazines in high yields. This method has been applied to N-benzylpyroglutamic acids, in the preparation of potential antifungal products.

Key words

pyroglutamic derivatives - lactams - imidodicarbonimidate zinc salt - heterocycles - triazines

References

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