Molbank 2006, M494

http://www.mdpi.org/molbank/

 

1-{[Benzyl-(2-cyano-ethyl)-amino]-methyl}-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester

 

Leila Herrag,1,2*  Rachid Touzani,1,3  Abdelkrim Ramdani1 and Belkheir Hammouti2

 

1 Laboratoire de Chimie Organique Physique, Département de Chimie , Faculté des Sciences , Université Mohammed Premier , B.P. 524, 60000 Oujda , Maroc.

2Laboratoire de Chimie des Eaux et Corrosion, Département de Chimie, Faculté des  Sciences,  B.P. 717, Oujda, Maroc.

3 Université Mohammed Premier, Faculté Pluridisciplinaire de Nador B.P. 300, 62700 Selouane, Nador, Maroc

E-mail: [email protected]

*Author to whom correspondence should be addressed

 

Received: 19 July 2006 / Accepted: 31 July 2006 / Published: 1 September 2006

 

Keywords: pyrazole; propionitrile and tridentate ligand.

 

The products of aza-type Michael addition, i.e., β-amino carbonyl compounds and their derivatives, are often used as peptide analogs or precursors of optically active amino acids, amino alcohols, diamines, and lactams [1]. Moreover, β-amino carbonyl functionalities are ubiquitous motifs in natural products such as alkaloids and polyketides [2]. Herein, we report the synthesis of new product using aza-type Michael reactions under mild conditions.

 

 

 

A mixture of 3-(benzylamino)propionitrile 1 [3] (1g, 6.25mmol) and 1-hydroxymethyl-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester 2 [4] (1.15g , 6.25 mmol) in 20 ml of acetonitrile was stirred at room temperature for four days, then the mixture was dried with Na2SO4 and filtered. The solvent was evaporated under reduced pressure. The product 3 obtained with an 81% yield as yellow oil.

 

1H-NMR (300 MHz, CDCl3): δ= 7.34 (CHarom, 5H,  s) ; 6.55 ( CHpyr, 1H,  s) ; 4.94 (pyr-CH2-N, 2H, s) ; 4.33-4.4 ( OCH2 , 2H, q, J = 8Hz) ; 3.750 (C6H5-CH2, 2H,  s) ; 3.00-3.1 (CH2-CH2-CN, 2H, t, J = 7.33Hz) ; 2.34-2.38 ( N-CH2, 2H,  t, J = 8Hz); 2.18 (CH3, 3H,  s) and 1.39-1.34 ( CH3, 3H, t, J = 8Hz).

 

13C-NMR (CDCl3, 75 MHz): δ= 162.94 (l); 143.26 (i); 141.432 (g); 137.51 (m); 129.16; 129.06 (n); 128.83 (f); 128.23 (o); 119.00 (a); 109.19 (h); 67.70 (e); 61.26 (k); 56.76 (d); 48.34 (c); 17.44 (b); 14.77 (p); 11.55 (j).

 

EI-MS (70 eV, m/z):  173; 171; 154 (51.4); 119; 91 (60.6).

 

References:

1. Fustero, S.; Pina, B.; Salavert, E.; Navarro, A.; Ramirez de Arellano, M. C.; Fuentes, A. S. J. Org. Chem. 2002, 67, 4667.

2. Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed 1998, 37, 1045.

3. a) Xu, L.W.; Li, L.; Xia, C.-G. Helvetica Chimica Acta, 2004, 87, 1522. b) Azizi, N.; Saidi, M. R.  Tetrahedron, 2004, 60, 383.

4. Touzani, R. ; Ramdani, A. ; El Kadiri, S.; Gourand, F. Molecules, 1999, 4, M116.

 

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