8,12-Diethyl-4,16-dimethyl-1,3,8,12,17,18-hexaazatricyclo[12.2.1.1^3,6]octadeca-4,6(18), 14(17), 15-tetraene

Farid Berhili ^a, Rachid Touzani ^a, Abdelkrim Ramdani ^a and Sghir El Kadiri ^b*

^a Laboratoire de Chimie Organique-Physique, Faculté des Sciences, Université Mohammed Ier Oujda, Maroc

^b Laboratoire de Chimie de l'Environnement et des Matériaux, Faculté des Sciences, Université Mohammed Ier Oujda, Maroc
* Fax : +212 56 50 06 03 E-mail: [email protected]

Received: 16 June 2002 / Accepted: 30 September 2002 / Published: 11 March 2003

Keywords: macrocyclic compounds, macrocyclic cavity, pyrazole

A suspension of sodium carbonate (12 g, 120 mmol) in acetonitrile (250 mL) was refluxed under magnetic stirring, then a solution of bis-(3-chloromethyl-5-methylpyrazolyl)methane (1) (2 g, 7 mmol) [1, 2] and diamine 2 (0.95 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 : 96/4) as eluent to give the macrocycle 3 as an oily substance.

Yield: (1.15 g, 50 %). 

(FAB)⁺ [M+H]⁺ = 331. 

¹H NMR (250 MHz, CDCl₃) d ppm: 6.00 (s, 2H, CH₂-NPz) ; 5.93 (s, 2H, H-Pz) ; 3.48 (s, 4H, Pz-CH₂-N) ; 2.60(q, 4H, N-CH₂-CH₃) ; 2.40 (s, 6H, CH₃-Pz) ; 2.13 (t, 4H, N-CH₂-CH₂) ; 1.57 (m, 2H, CH₂-CH₂-CH₂) ; 1.10 (t, 6H, N-CH₂-CH₃).

References

1. El Kadiri, S.; Ph. D. Thesis, U. S. T. L. Montpellier, 1988.

2. Malek, F.; Persin, M.; Ramdani, A.; Sarrasin, J.; Zidane, I. New. J. Chem. 2002, 2, 26.

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