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6,19-Dimethyl-10,15-bis(pyridin-2-ylmethyl)-1,5,10,15,20,21-hexaaza-tricyclo[15.2.1.15,8]heneicosa-6,8(21),17(20),18-tetraene
 
 
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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

1
Laboratoire de Chimie Organique-Physique, Département de Chimie, Faculté Des Sciences, Université Mohamed Premier, 60000 Oujda, Maroc
2
Laboratoire de Chimie de l`Environnement et des Matériaux, Département de Chimie, Faculté Des Sciences, Université Mohamed Premier, 60000 Oujda, Maroc
*
Author to whom correspondence should be addressed.
Molbank 2005, 2005(5), M444; https://doi.org/10.3390/M444
Submission received: 27 June 2005 / Accepted: 10 August 2005 / Published: 1 November 2005
Despite the numerous polydentate macrocyclic structures already described as neutral receptors for various substrates [1,2,3], 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].
Molbank 2005 m444 i001
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]+.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References

  1. Izatt, R. M.; Christensen, J. J. Progress in Macrocyclic Chemistry; Wiley-Interscience: New York, 1979; Vol. 1, 1981, Vol. 2. [Google Scholar]
  2. Melson, G. A. Coordination Chemistry of Macrocycles; Plenum: New York, 1979. [Google Scholar]
  3. Bol, J. E.; Driessen, W. L.; Reedijk, J. J. Chem. Soc. Chem. Comm. 1995, 1365.
  4. Lindoy, L. F. The Chemistry of Macrocyclic Ligand Complexes; Cambridge University Press: Cambridge, 1988. [Google Scholar]
  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.; Vachet, R. W. Inorganica Chimica Acta 2004, 357, 1141.
  • Sample Availability: Available from MDPI.

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MDPI and ACS Style

Touzani, R.; Ramdani, A.; El Kadiri, S. 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. Molbank 2005, 2005, M444. https://doi.org/10.3390/M444

AMA Style

Touzani R, Ramdani A, El Kadiri S. 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. Molbank. 2005; 2005(5):M444. https://doi.org/10.3390/M444

Chicago/Turabian Style

Touzani, Rachid, Abdelkrim Ramdani, and Sghir El Kadiri. 2005. "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" Molbank 2005, no. 5: M444. https://doi.org/10.3390/M444

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