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Molbank 2005, M444 |
7,19-Dimethyl-11,15-bis(pyridin-2-ylmethyl)-1,6,11,15,20,21-hexaaza-tricyclo[15.2.1.16,9]heneicosa-7,9(21),17(20),18-tetraene
Rachid Touzani,a
Abdelkrim Ramdania
et Sghir El Kadiri.b*
aLaboratoire de Chimie
Organique-Physique
b*Laboratoire de Chimie de l`Environnement
et des Matériaux
Département
de Chimie, Faculté Des Sciences, Université Mohamed Premier,
60000
Oujda, Maroc
e-mail: [email protected]
Received: Received:
Keywords: macrocyclic
compounds, macrocyclic cavity, pyrazol.
Despite the numerous polydentate macrocyclic structures already described as neutral
receptors for various substrates [1-3], the search for new receptor families is
still important with a view to obtaining molecules capable of molecular
recognition, transport, selective catalysis or biological models.
In this work, we were interested in mixed donor macrocycle incorporating sp3 and sp2 nitrogens; some receptors of this type have been described
to the cyclam family and are obtained from 2,6 disubstituted pyridines [4,5].
A suspension of sodium carbonate (12 g, 120 mmol) in acetonitrile (250 mL) was refluxed under magnetic stirring, then a solution
of 1,4-bis(3-chloromethyl-5-methylpyrazolyl)butane 1 (2.1 g, 7 mmol) [1] and N,N'-bis(pyridin-2-ylmethyl)propane-1,3-diamine
2 (1.8 g , 7 mmol) [6] in acetonitrile
(50 mL) was added dropwise.
The solution was refluxed under stirring for two hours, filtered and the
solvent was removed in vacuum, the residue was purified on alumina column with
(CH2Cl2/MeOH: 95/5) as eluent
to give the 2.70 g (70% yield) macrocycle 3 as
an oily substance.
1H-NMR (250 MHz; CDCl3): δ= 8.49 Ha;
7.60 Hc; 7.53 Hd;
7.10 Hb; 5.88 (s, 2H, H4); 4.00
(t, 4H, H6); 3.89 (s, 4H, H3); 3.51 (s, 4H, H1');
2.40 (t, 4H, H2); 2.24 (d, 6H, H5); 1.70 (t, 2H, H1);
1.70 (m, 4H, H7).
MS
(FAB; m/z): 499 [M+H]+.
References:
1. Izatt R. M.; Christensen J. J. Progress in Macrocyclic
Chemistry, Wiley-Interscience, New York , 1979,
Vol. 1, 1981, Vol. 2.
2. Melson G. A.;,
Coordination Chemistry of Macrocycles, Plenum,
3. Bol, J. E.; Driessen,
W. L. and Reedijk, J.., J. Chem. Soc. Chem. Comm., 1995,
1365.
4. Lindoy L. F. The Chemistry of Macrocyclic
Ligand Complexes,
5. Hancok R. D.; Martell A. E . Chem. Rev., 1989, 89, 1875
6. Hartman, J. A. R.; Kammier, A.
L.; Spracklin, R. J.; Pearson, W. H.;, Combariza, M. Y. and Vachet, R.
W. Inorganica Chimica
Acta, 2004, 357, 1141.
Sample Availability: Available from MDPI.
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