Facile Synthesis of Novel Pyrimido[1,2-a]pyrimidin-4-ones from Highly Reactive Malonates

被引:10
作者
Gullu, Mustafa [1 ]
Dincsonmez, Ali [1 ]
Ozyavas, Oznur [1 ]
机构
[1] Ankara Univ, Fac Sci, Dept Chem, TR-06100 Ankara, Turkey
关键词
Nitrogen heterocycles; Fused-ring systems; Cyclization; Condensation; Malonates; REGIOSELECTIVE SYNTHESIS; HETEROCYCLES; DERIVATIVES; PYRIMIDINE; INHIBITORS; GUANIDINE; ACRYLONITRILE; HYDROXY; ANALOGS;
D O I
10.1002/ejoc.200901419
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A very simple and efficient procedure for the synthesis of novel 2-hydroxy-4H-pyrimido[1,2-a]pyrimidin-4-ones is described. Title compounds were obtained from the room temperature reaction of 2-aminopyrimidine and its substituted derivatives with bis(2,4,6-trichlorophenyl) malonates. High product yields were observed under optimized conditions. Applicability and reactivity of a range of substituted and unsubstituted phenyl malonates were also investigated. Structural identification of all new compounds was accomplished by spectroscopic methods and elemental analysis.
引用
收藏
页码:2113 / 2120
页数:8
相关论文
共 44 条
[1]   NEW SYNTHESIS OF IMIDAZO[1,2-A]PYRIMIDINES AND PYRIMIDO[1,2-A]PYRIMIDINES [J].
ABDELFATTAH, AM ;
SHERIF, SM ;
ELREEDY, AM ;
GADALLA, SA .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1992, 70 (1-2) :67-73
[2]   A new, one-pot, three-component synthesis of 4H-pyrido[1,2-a]-pyrimidines, 4H-pyrimido[1,2-a]pyrimidines, and 4H-pyrazino[ 1,2-a] pyrimidines [J].
Adib, Mehdi ;
Sayahi, Mohammad Hosein ;
Ziyadi, Hakimeh ;
Bijanzadeh, Hamid Reza ;
Zhu, Long-Guan .
TETRAHEDRON, 2007, 63 (45) :11135-11140
[3]   ALKYLATION OF 2-AMINO-4-HYDROXYPYRIMIDINES WITH ACRYLONITRILE AND WITH DIMETHYL SULFATE - 2 PYRIMIDO[1,2-A]PYRIMIDINEDIONES [J].
ANGIER, RB ;
CURRAN, WV .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (06) :1891-&
[4]  
BAKER BR, 1968, J MED CHEM, V11, P475, DOI 10.1021/jm00309a015
[5]  
BERNIER JL, 1980, J PHARM SCI-US, V69, P1343, DOI 10.1002/jps.2600691128
[6]   Chemistry of stable iminopropadienones, RN=C=C=C=O [J].
Bibas, H ;
Moloney, DWJ ;
Neumann, R ;
Shtaiwi, M ;
Bernhardt, PV ;
Wentrup, C .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (08) :2619-2631
[7]   SUBSTITUTED SULFANILAMIDOPYRIMIDINES [J].
BRAKER, W ;
PRIBYL, EJ ;
SHEEHAN, JT ;
SPITZMILLER, ER ;
LOTT, WA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1947, 69 (12) :3072-3078
[8]   SYNTHESIS OF PYRIMIDO[4,5-D]PYRIMIDINE [J].
BREDERECK, H ;
SIMCHEN, G ;
KRAMER, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1969, 8 (05) :383-+
[9]   Synthesis of pyrrolo[2,3-d]pyrimidines that are structurally related to methylated guanosines from tRNA and the nucleoside Q analogs, PreQ(0) and PreQ(1) [J].
Cheng, CS ;
Hoops, GC ;
Earl, RA ;
Townsend, LB .
NUCLEOSIDES & NUCLEOTIDES, 1997, 16 (04) :347-364
[10]  
CHEREZE N, 2005, Patent No. 2005058908