Molbank 2006, M472

http://www.mdpi.net/molbank/

 

1-(ethoxycarbonylmethyl)-3-(1¡¯-tolyl-3¡¯-(ethoxycarbonyl)5¡¯-hydroxypyrazolyl)-2-oxo quinoxaline 

 

Souad Ferfra,Noureddine H.Ahabchane, El Mokhtar Essassi*

 

Laboratoire de Chimie Organique H¨¦t¨¦rocyclique, Facult¨¦ des Sciences, BP 1014, Avenue Ibn Batouta, Rabat, Maroc

e-mail:  [email protected]

*Author to whom correspondence should be addressed

 

Received: 13 February 2006 / Accepted: 18 February 2006/ Published: 28 February 2006

 

Keywords: cyclocondensations, quinoxaline, hydrazonoyl bromide

 


 

To a solution of hydrazonoyl bromide (5.70 g, 0.02 mol) 2 and 1 [1]  (3.18 g, 0.01 mol) in tetrahydrofuran (60 ml) was added triethylamine (2.02 g, 0.02 mol in 10 ml of THF). The reaction mixture was refluxed for 48 hours. The solvent was evaporated under reduced pressure and the resulting crude material was chromatographied over silica gel column using 10:90 ethylacetate:hexane as eluent (yield 70%).

 

Melting point: 182-184¡ãC

 

IR (KBr , cm-1 ): 1640 ( nN-C=O); 1720 (nN-C=O).

 

1H- NMR ( 250 MHz, CDCl3): d=  7.81-7.04 (8H, m, H arom); 5.02 (2H, s, NCH2); 4.44 (2H, q, J=7 Hz, CH2); 4.25 (2H, q, J = 7 Hz, CH2);  2.36 (3H, s, CH3-¦µ);  1.37 (3H, t, J = 7 Hz, CH3); 1.27 (3H, t, J = 7 Hz, CH3).

 

13C- NMR (250MHz, CDCl3): d= 166.5 (Cq); 164.2 (Cq); 161.6 (Cq); 154.5 (Cq); 143.8 (Cq); 143.4 (Cq); 135.9 (Cq); 135.5 (Cq); 129.4 (CHar); 129.1 CHar); 129.1 (Cq); 127.8 (CHar); 126.8 (Cq); 125.3 (CHar); 122.0 (CHar); 120.7 (CHar); 114.0 (CHar); 96 (C4); 62.3 (CH2); 61.7 (CH2); 44.2 (NCH2);  21.0 (¦µ-CH3); 14.2 (CH3).

 

MS (IE): 476

 

Reference

1. Ferfra, S. Ahabchane N.H., Essassi, E. M.; Molecules, submitted

 

Sample Availability: Available from MDPI.

 

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