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

被引:15
作者
Oudir, Souhila
Rigo, Benoit
Henichart, Jean-Pierre
Gautret, Philippe
机构
[1] Ecole Hautes Etud Ingenieur, F-59046 Lille, France
[2] Univ Lille 2, Inst Chim Pharmaceut Albert Lespagnol, Grp Rech Inhibit Proliferat Cellulaire, EA 2692, F-59006 Lille, France
来源
SYNTHESIS-STUTTGART | 2006年 / 17期
关键词
pyroglutamic derivatives; lactams; imidodicarbonimidate zinc salt; heterocycles; triazines;
D O I
10.1055/s-2006-942519
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:2845 / 2848
页数:4
相关论文
共 18 条
[1]   STUDIES ON PYRROLIDINONES - SYNTHESIS OF 2-(5-OXO-2-PYRROLIDINYL)-1,3,4-OXADIAZOLES AND 2-(5-OXO-2-PYRROLIDINYL)BENZIMIDAZOLES [J].
CAULIEZ, P ;
COUTURIER, D ;
RIGO, B ;
FASSEUR, D ;
HALAMA, P .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1993, 30 (04) :921-927
[2]  
CHIONG GC, 1990, Patent No. 4933450
[3]  
Fanelli C., 1998, 7 INT C PLANT PATH E
[4]  
Gates P.S., 1993, PCT Int. Appl., Patent No. [WO 9309099 A2, 9309099]
[5]   TRIAZINES .18. THE REACTION OF ALIPHATIC DIAZOCOMPOUNDS WITH CHLORO-S-TRIAZINES [J].
GRUNDMANN, C ;
KOBER, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (04) :944-948
[6]  
GRUNDMANN C, 1962, Patent No. 3022303
[7]   TRIAZINES .21. THE PREPARATION OF S-TRIAZINE ALDEHYDES [J].
KOBER, E ;
GRUNDMANN, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (20) :5547-5551
[8]   CONVERSION OF TRICHLOROMETHYL GROUPS INTO DICHLOROMETHYL GROUPS [J].
KOBER, E .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (07) :2270-&
[9]  
KOBER E, 1965, Patent No. 3226386
[10]  
PAULY M, 1985, Patent No. 135144