Molbank 2005, M440

http://www.mdpi.net/molbank/

 

6,10,14,18-Tetramethyl-1,5,10,14,19,20-hexaaza-tricyclo[14.2.1.15,8]eicosa-6,8(20),16(19),17-tetraene

 

Rachid Touzani,1 Abdelkrim Ramdani1 et Sghir El Kadiri2*

 

1) Laboratoire de Chimie Organique-Physique,

2) 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: 21 July 2005 / Published: 1 October 2005

 

Keywords: macrocyclic compounds, macrocyclic cavity, pyrazole

 

Macrocyclic chemistry is one of the fastest growing fields in chemistry. Studies of molecular recognition, transport biological aspets, selective catalysis the macrocycle containing the mixed sites of coordination, complexing with Ru (II) gives catalytic properties of SOD type and catalase [1-2], inclusion phenomena, organic synthesis and industrial applications of macrocyclic compounds are all burgeoning in many directions. In this work we describe the synthesis of new macrocyclic ligand containing pyrazol and aminic coordination sites.

 

 

A suspension of sodium carbonate (12 g, 120 mmol) in acetonitrile (250 mL) was refluxed under magnetic stirring, then a solution of 1,3-bis (3-chloromethyl-5-methylpyrazolyl)propane 1 (2.1 g, 7 mmol) [1, 2] 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 1.62 g (yield 70 %) macrocycle 3 as an oily substance.

 

1H-NMR (250MHz, CDCl3): δ= 5.90 (s, 2H, H-4); 4.00 (t, 4H, H-6); 3.59 (s, 4H, H-3); 2.52 (t, 4H, H-2); 2.39 (s, 6H, H-1'); 2.26 (d, 6H, H-5); 2.26 (t, 2H, H-7); 1.70 (m, 2H, H-1).

 

MS-FAB (m/z): 331 [M+H]+.

 

References:

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

2.Bienvenue, E.; Choua, S.; Lobo-Recio, M-HAS.; Marzin, C.; Pacheco, P.; Seta, P. and Tarrago, G.  J. Inorg. Biochem., 1995, 57, 157.

 

Sample Availability: Available from MDPI.

 

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