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8,12-Dibenzyl-4,16-dimethyl-1,3,8,12,17,18-hexaazatricyclo[12.2.1.13,6]octadeca-4,6(18), 14(17), 15-tetraene
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10,14-Dibenzyl-6,18-dimethyl-1,5,10,14,19,20-hexaazatricyclo[14.2.1.15,8]icosa-6,8(20), 16(19), 17-tetraene

1
Laboratoire de Chimie Organique-Physique, Faculté des Sciences, Université Mohammed Ier Oujda, Maroc
2
Laboratoire de Chimie de l'Environnement et des Matériaux, Faculté des Sciences, Université Mohammed Ier Oujda, Maroc
*
Author to whom correspondence should be addressed.
Molbank 2003, 2003(1), M312; https://doi.org/10.3390/M312
Received: 16 June 2002 / Accepted: 30 September 2002 / Published: 11 March 2003

Excerpt

Note: In lieu of an abstract, this is an excerpt from the first page.

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)propane (1) (2.03 g, 7 mmol) [1-3] and diamine 2 (1.86 g , 7 mmol) in acetonitrile (50 mL) was added dropwise.[...]
Keywords: macrocyclic compounds, macrocyclic cavity, pyrazole macrocyclic compounds, macrocyclic cavity, pyrazole
Molbank 2003 m312 i001
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)propane (1) (2.03 g, 7 mmol) [1,2,3] and diamine 2 (1.86 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 : 97/3) as eluent to give the macrocycle 3 as an oily substance.
Yield: (2 g, 70 %).
(FAB)+ [M+H]+ = 485.
1H NMR (250 MHz, CDCl3) d ppm: 7.40 (m, 10H, Ph) ; 5.85 (s, 2H, HPz) ; 3.95 (t, 4H, CH2-Pz) ;3.60 (s, 4H, N-CH2-Ph) ; 3.50 (s, 4H, Pz-CH2-N) ; 2.45 (t, 4H, N-CH2-CH2) ; 2.40 (m, 2H, N-CH2-CH2) ; 2.20 (s, 6H, CH3-Pz) ;1.30 (m, 2H, CH2-CH2-CH2).

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References

  1. Tarrago, G.; El Kadiri, S.; Marzin, C.; Coquelet, C. New J. Chem. 1991, 15, 677.
  2. Bienvenue, E.; Choua, S.; Lobo-Recio, M-Has.; Marzin, C.; Pacheco, P.; Seta, P.; Tarrago, G. Inorg. Biochem. 1995, 57, 157.
  3. Bol, J. E.; Driessen, W. L.; Reedjik, J. J. Chem. Soc., Chem. Commun 1995, 13, 65.
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