Molbank 2006, M493 |
1-{[Benzyl-(2-cyano-ethyl)-amino]-methyl}-5-methyl-1H-pyrazole-3-carboxylic
acid methyl ester
Leila Herrag,1,2*
Rachid
Touzani,1,3 Abdelkrim Ramdani1 and Belkheir
Hammouti2
1 Laboratoire de Chimie Organique Physique, D¨¦partement de Chimie , Facult¨¦ des Sciences , Universit¨¦ Mohammed Premier , B.P. 524, 60000 Oujda , Maroc.
2Laboratoire de Chimie
des Eaux et Corrosion, D¨¦partement
de Chimie, Facult¨¦ des Sciences, B.P. 717,
3 Universit¨¦ Mohammed Premier, Facult¨¦ 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 nitrogen donor ligand.
The
products of aza-type Michael addition, i.e.,
¦Â-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, ¦Â-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 methyl
ester 2 [4] (1.062g ; 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 has been obtained with a 99% yield as
yellow oil.
1H-NMR (300 MHz, CDCl3): ¦Ä= 7.31 (CHarom, 5H, s) ; 6.56 ( CHpyr,1H, s) ; 4.94
(OCH3, 3H, s) ; 3.89 ( N-CH2-N, 2H, s) ;
3.75 (C6H5-CH2 ,2H, s) ; 3.01-3.06 (CH2-CH2-CN,
2H, t, J = 7.33 Hz) ; 2.33-2.37 (
N-CH2 , t, J = 7 Hz) and 2.18 ( CH3, 3H, s).
13C-NMR (CDCl3, 75 MHz): ¦Ä= 163.32 (l); 142.91 (i); 141.56 (g); 137.46 (m); 129.154 (n); 129.03; 129.08
(f); 128.26 (o); 118.97 (a); 109.30 (h); 67.82 (e); 56.79 (d); 52.37 (k); 48.36
(c); 17.46 (b); 11.55 (j).
EI-MS
(70 eV, m/z): 173 (16); 171; 119 (22); 91 (100).
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.
© 2006 MDPI. All rights reserved.