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
[1]   The synthesis of pyrimidin-4-yl substituted α-amino acids.: A versatile approach from alkynyl ketones [J].
Adlington, RM ;
Baldwin, JE ;
Catterick, D ;
Pritchard, GJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (08) :855-866
[2]  
[Anonymous], J HETEROCYCLIC CHEM
[3]   A novel catalytic and highly enantioselective approach for the synthesis of optically active carbohydrate derivatives [J].
Audrain, H ;
Thorhauge, J ;
Hazell, RG ;
Jorgensen, KA .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) :4487-4497
[4]   STUDIES ON THE NACTINS - TOTAL SYNTHESIS OF (+/-)-TERT-BUTYL 8-O-(TERT-BUTYLDIMETHYLSILYL)NONACTATE [J].
BARRETT, AGM ;
SHETH, HG .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (25) :5017-5022
[5]   ENANTIODIVERGENT SYNTHESES OF (+)-NONACTIC AND (-)-NONACTIC ACID AND THE TOTAL SYNTHESIS OF NONACTIN [J].
BARTLETT, PA ;
MEADOWS, JD ;
OTTOW, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (18) :5304-5311
[6]   Syntheses and biological evaluation of 3-substituted amino-1-aryl-6-hydroxy-hex-2-ene-1-ones as antioxidant and hypolipidemic agents [J].
Batra, S ;
Srivastava, S ;
Singh, K ;
Chander, R ;
Khanna, AK ;
Bhaduri, AP .
BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (08) :2195-2209
[7]   ISOLATION OF A NEW AMINO ACID FROM LATHYRUS TINGITANUS [J].
BELL, EA .
BIOCHIMICA ET BIOPHYSICA ACTA, 1961, 47 (03) :602-&
[8]   Synthesis of functionalized furans based on a '[3+2] cyclization/bromination/elimination' strategy [J].
Bellur, E ;
Langer, P .
SYNTHESIS-STUTTGART, 2006, (03) :480-488
[9]   Synthesis of benzofurans with remote bromide functionality by domino "ring-cleavage-deprotection-cyclization" reactions of 2-alkylidenetetrahydrofurans with boron tribromide [J].
Bellur, E ;
Langer, P .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (19) :7686-7693
[10]   Efficient synthesis of furan-2-ylacetates, 7-(alkoxycarbonyl)benzofurans, and 7-(alkoxycarbonyl)-2,3-dihydrobenzofurans based on cyclization reactions of free and masked dianions: A "cyclization/dehydrogenation" strategy [J].
Bellur, E ;
Langer, P .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (24) :10013-10029