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Synthesis 2006(17): 2845-2848
DOI: 10.1055/s-2006-942519
DOI: 10.1055/s-2006-942519
PAPER
© Georg Thieme Verlag Stuttgart · New YorkA Convenient Method for the Conversion of a Carboxy Group into a 4,6-Dimethoxy-1,3,5-triazine Group: Application to N-Benzylpyroglutamic Acids
Further Information
Received
22 March 2006
Publication Date:
25 July 2006 (online)
Publication History
Publication Date:
25 July 2006 (online)
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
- 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, andSaunders 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, andGreen D. inventors; Ger. Offen. 19521355 A1. ; Chem. Abstr. 1997, 126, 144293 - 5e
Weiss S, andKrommer 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, andKober 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