Molbank 2005, M441

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7,11,15,19-Tetramethyl-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 Kadirib*

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: 27 June 2005 / Accepted: 10 August 2005 / Published: 1 November 2005

 

Keywords: macrocyclic compounds, macrocyclic cavity, pyrazole

 

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, and biological models.

In this work, we are interested in the synthesis of mixed donor macrocycles 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 (2.2 g, 7 mmol) [6], and N,N'-dimethyl-propane-1,3-diamine 2 (0.71 g , 7 mmol) 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 eluant to give 1.7 g (70 %) of macrocycle 3 as an oily substance.

 

1H NMR (250 MHz; CDCl3): δ= 5.90 (s, 2H, H4); 4.00 (t, 4H, H6); 3.50 (s, 4H, H3); 2.40 (s, 6H, H1'); 2.20 (d, 6H, H5); 2.19 (m, 4H, H2); 1.70 (m, 4H, H7); 1.65 (m, 2H, H1).

 

MS (FAB; m/z): 345 [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, New York, 1979.

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, Cambridge University Press, Cambridge, 1988.

5. Hancok  R. D.; Martell A. E ., Chem. Rev., 1989, 89, 1875

6. Tarrago, G.; El Kadiri, S.; Marzin, C. and Coquelet, C. New. J. Chem., 1991, 15, 677.

 

Sample Availability: Available from MDPI.

 

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