Solvent-free synthesis and structural characterization of azolyl-substituted pyrimidines

被引:6
作者
de la Hoz, A [1 ]
Blasco, H
Díaz-Ortiz, A
Elguero, J
Foces-Foces, C
Moreno, A
Sánchez-Migallón, A
Valiente, G
机构
[1] Univ Castilla La Mancha, Fac Quim, Dept Quim Organ, E-13071 Ciudad Real, Spain
[2] CSIC, Inst Quim Med, E-28006 Madrid, Spain
[3] CSIC, Inst Quim Fis Rocasolano, Dept Cristalog, E-28006 Madrid, Spain
关键词
D O I
10.1039/b200169c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Base-catalyzed trimerization of N-cyanomethylazoles under pressure and in solvent-free conditions a orded 4-amino-2,6-bis(azol-1-ylmethyl)-5-(azol-1-yl) pyrimidines (1-3) in 33 67% yields. The structures of these compounds was determined by a combination of NMR techniques and X-ray crystallography. The 4-amino groups show a restricted rotation around the C-N bond; the free energy of activation for this process was determined by variable temperature experiments. In the crystal structure of the pyrazol-1-yl derivative, the amino group shows a distorted planar geometry in both independent molecules and acts as a double hydrogen bond donor towards two of the three pyrazole rings, forming ribbons of R-2(2)(10) rings.
引用
收藏
页码:926 / 932
页数:7
相关论文
共 30 条
[21]   S-TRIAZOLOPYRIMIDINES .2. SYNTHESIS AS POTENTIAL THERAPEUTIC AGENTS [J].
MILLER, GW ;
ROSE, FL .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (MAY) :3357-&
[22]   Automated assignment of graph-set descriptors for crystallographically symmetric molecules [J].
Motherwell, WDS ;
Shields, GP ;
Allen, FH .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 2000, 56 :466-473
[23]   From molecules to crystal engineering: Supramolecular isomerism and polymorphism in network solids [J].
Moulton, B ;
Zaworotko, MJ .
CHEMICAL REVIEWS, 2001, 101 (06) :1629-1658
[24]   Synthesis of substituted 2-amino-4,6-bis(nonafluoro-tert-butyl)1,3,5-triazines [J].
Popov, AV ;
Shastin, AV ;
Luzina, EL ;
Pushin, AN ;
Gavrishova, TN .
RUSSIAN CHEMICAL BULLETIN, 1999, 48 (08) :1548-1552
[25]   ROTATIONAL-ISOMERISM IN 5-AMINO-6-(N-METHYLFORMAMIDO)-AS-TRIAZIN-3(2H)-ONE [J].
RIAND, J ;
TANGUY, M ;
CHENON, MT ;
TZENG, CC ;
PANZICA, RP .
MAGNETIC RESONANCE IN CHEMISTRY, 1990, 28 (06) :505-509
[26]  
RONZIO AR, 1995, ORG SYNTH, V3, P71
[27]  
Sandstrom J., 1982, DYNAMIC NMR SPECTROS, P96
[28]  
Seitz O, 1999, ANGEW CHEM INT EDIT, V38, P3466, DOI 10.1002/(SICI)1521-3773(19991203)38:23<3466::AID-ANIE3466>3.0.CO
[29]  
2-X
[30]   IN A MODEL C-G BASE PAIR, ONE AMINO GROUP ROTATES AND THE OTHER DOES NOT [J].
WILLIAMS, LD ;
WILLIAMS, NG ;
SHAW, BR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) :829-833