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Asymmetric Synthesis of a New Monocyclic β-Lactam as a potential biological active compound
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Laboratoire de Chimie Organique-Physique, Département de Chimie, Faculté Des Sciences, Université Mohamed Premier, 60000 Oujda, Maroc
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(4), M440;
Received: 27 June 2005 / Accepted: 21 July 2005 / Published: 1 October 2005
Keywords: macrocyclic compounds; macrocyclic cavity; pyrazole 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.
Molbank 2005 m440 i001
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]+.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3


  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. J. Inorg. Biochem. 1995, 57, 157.
  • Sample Availability: Available from MDPI.
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