First functionalization by metallation of the pyridine moiety of 4-methoxypyridopyrimidines.: Diazines:: Part 38

被引:15
作者
Audoux, J [1 ]
Plé, N [1 ]
Turck, A [1 ]
Quéguiner, G [1 ]
机构
[1] INSA, IRCOF, UMR 6014, Lab Chim Organ Fine & Heterocycl, F-76131 Mont St Aignan, France
关键词
metallation; methoxypyridopyrimidines; functionalization;
D O I
10.1016/j.tet.2004.05.061
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Starting from pyridopyrimidin-4(3H)-ones, a general synthetic route leading to 4-methoxypyridopyrimidines is described. The first lithiation and functionalization of the pyridine moiety has been studied. According to various structural parameters, the regioselectivity of the metallation is discussed. The functionalization of the 4-methoxypyridopyrimidines via the metallation reaction, provides an efficient process to access new substituted pyridopyrimidines. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6353 / 6362
页数:10
相关论文
共 29 条
[1]   DEVELOPMENT OF ETHYL 3,4-DIHYDRO-4-OXOPYRIMIDO[4,5-B]QUINOLINE-2-CARBOXYLATE, A NEW PROTOTYPE WITH ORAL ANTIALLERGY ACTIVITY [J].
ALTHUIS, TH ;
MOORE, PF ;
HESS, HJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1979, 22 (01) :44-48
[2]   STRUCTURE-ACTIVITY-RELATIONSHIPS IN A SERIES OF NOVEL 3,4-DIHYDRO-4-OXOPYRIMIDO[4,5-B]QUINOLINE-2-CARBOXYLIC ACID ANTIALLERGY AGENTS [J].
ALTHUIS, TH ;
KADIN, SB ;
CZUBA, LJ ;
MOORE, PF ;
HESS, HJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1980, 23 (03) :262-269
[3]   PYRIDOPYRIMIDINES .6. NUCLEOPHILIC SUBSTITUTIONS IN PYRIDO[2,3-D]PYRIMIDINE SERIES [J].
ANDERSON, GL ;
SHIM, JL ;
BROOM, AD .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (06) :993-996
[4]  
[Anonymous], 1976, US Patent, Patent No. 3947416
[5]  
Armarego W. M. F., 1967, FUSED PYRIMIDINES 1
[6]  
AUDOUX J, UNPUB
[7]   Diastereoisomeric atropisomers of peri-substituted naphthamides:: synthesis, stereoselectivity and stability [J].
Clayden, J ;
Westlund, N ;
Wilson, FX .
TETRAHEDRON LETTERS, 1999, 40 (45) :7883-7887
[8]   Structure-activity studies of 5-substituted pyridopyrimidines as adenosine kinase inhibitors [J].
Cowart, M ;
Lee, CH ;
Gfesser, GA ;
Bayburt, EK ;
Bhagwat, SS ;
Stewart, AO ;
Yu, HX ;
Kohlhaas, KL ;
McGaraughty, S ;
Wismer, CT ;
Mikusa, J ;
Zhu, C ;
Alexander, KM ;
Jarvis, MF ;
Kowaluk, EA .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (01) :83-86
[9]  
GAUTHERONCHAPOU.V, 1999, TETRAHEDRON, V55, P5389
[10]  
Huber B. S., 1968, J MED CHEM, V11, P708