Synthesis of 4-(3-hydroxyalkyl)pyrimidines by ring transformation reactions of 2-alkylidenetetrahydrofurans with amidines

被引:25
作者
Bellur, Esen
Langer, Peter
机构
[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany
[2] Ernst Moritz Arndt Univ Greifswald, Inst Chem & Biochem, D-17487 Greifswald, Germany
[3] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany
关键词
Amidines; heterocycles; pyrimidines; ring transformation; tetrahydrofurans;
D O I
10.1016/j.tet.2006.03.069
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Domino reactions of amidines with 2-alkylidenetetrahydrofurans, prepared by cyclization of 1,3-dicarbonyl dianions or 1,3-bissilyl enol ethers with various dielectrophiles, provided an efficient access to 4-(3-hydroxyalkyl)pyrimidines. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5426 / 5434
页数:9
相关论文
共 59 条
[41]  
2-V
[42]   WITTIG AND HORNER-WITTIG COUPLING REACTIONS OF 2-SUBSTITUTED CYCLIC ETHERS AND THEIR APPLICATION TO SPIROKETAL SYNTHESIS [J].
LEY, SV ;
LYGO, B ;
ORGAN, HM ;
WONNACOTT, A .
TETRAHEDRON, 1985, 41 (18) :3825-3836
[44]   PHEROMONE SYNTHESIS .28. SYNTHESIS OF OPTICALLY-ACTIVE 2-ETHYL-1,6-DIOXASPIRO[4.4]NONANE (CHALCOGRAN), THE PRINCIPAL AGGREGATION PHEROMONE OF PITYOGENES-CHALCOGRAPHUS (L) [J].
MORI, K ;
SASAKI, M ;
TAMADA, S ;
SUGURO, T ;
MASUDA, S .
TETRAHEDRON, 1979, 35 (13) :1601-1605
[45]   ASYMMETRIC HYDROGENATION OF OLEFINS WITH APROTIC OXYGEN FUNCTIONALITIES CATALYZED BY BINAP RU(II) COMPLEXES [J].
OHTA, T ;
MIYAKE, T ;
SEIDO, N ;
KUMOBAYASHI, H ;
TAKAYA, H .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (02) :357-363
[46]  
OIVIN TLB, 1987, TETRAHEDRON, V43, P3309
[47]  
Pattenden G., 1978, PROG CHEM NAT PROD, V35, P133
[48]  
PEMMSIN M, 1988, EUR J CHEM, V23, P543
[49]   CYCLIZATION OF 6-HYDROXY-2-YNALS AND YNOATES - A NEW PATHWAY TO SUBSTITUTED 2-METHYLENE-TETRAHYDROFURANS [J].
PFLIEGER, D ;
MUCKENSTURM, B .
TETRAHEDRON, 1989, 45 (07) :2031-2040
[50]   RECENT ADVANCES IN CHEMISTRY OF UNSATURATED LACTONES [J].
RAO, YS .
CHEMICAL REVIEWS, 1976, 76 (05) :625-694